diff --git a/Rakefile b/Rakefile
index 3a5876fceaa..a29cb33859e 100644
--- a/Rakefile
+++ b/Rakefile
@@ -261,6 +261,9 @@ TEST_METADATA = {
     'redis-4' => '❌ 2.1 / ❌ 2.2 / ❌ 2.3 / ✅ 2.4 / ✅ 2.5 / ✅ 2.6 / ✅ 2.7 / ✅ 3.0 / ✅ 3.1 / ✅ 3.2 / ✅ 3.3 / ✅ jruby',
     'redis-5' => '❌ 2.1 / ❌ 2.2 / ❌ 2.3 / ❌ 2.4 / ✅ 2.5 / ✅ 2.6 / ✅ 2.7 / ✅ 3.0 / ✅ 3.1 / ✅ 3.2 / ✅ 3.3 / ✅ jruby'
   },
+  'routetest' => {
+    'multi-rack-app' => '❌ 2.1 / ❌ 2.2 / ❌ 2.3 / ❌ 2.4 / ✅ 2.5 / ✅ 2.6 / ✅ 2.7 / ✅ 3.0 / ✅ 3.1 / ✅ 3.2 / ✅ 3.3 / ✅ jruby'
+  },
   'appsec:rack' => {
     # Non-deprecated form of Regexp.new does not backport to Rack 1.x, see: https://github.com/rack/rack/pull/1998
     'rack-1' => '✅ 2.1 / ✅ 2.2 / ✅ 2.3 / ✅ 2.4 / ✅ 2.5 / ✅ 2.6 / ✅ 2.7 / ✅ 3.0 / ✅ 3.1 / ✅ 3.2 / ❌ 3.3 / ✅ jruby',
@@ -343,7 +346,7 @@ namespace :spec do
   task all: [:main, :benchmark,
              :rails, :railsredis, :railsredis_activesupport, :railsactivejob,
              :elasticsearch, :http, :redis, :sidekiq, :sinatra, :hanami, :hanami_autoinstrument,
-             :profiling]
+             :profiling, :routetest]
 
   desc '' # "Explicitly hiding from `rake -T`"
   RSpec::Core::RakeTask.new(:main) do |t, args|
@@ -378,6 +381,12 @@ namespace :spec do
     t.rspec_opts = args.to_a.join(' ')
   end
 
+  desc '' # "Explicitly hiding from `rake -T`"
+  RSpec::Core::RakeTask.new(:routetest) do |t, args|
+    t.pattern = 'spec/datadog/tracing/contrib/http_route_spec.rb'
+    t.rspec_opts = args.to_a.join(' ')
+  end
+
   desc '' # "Explicitly hiding from `rake -T`"
   RSpec::Core::RakeTask.new(:railsredis) do |t, args|
     t.pattern = 'spec/datadog/tracing/contrib/rails/**/*redis*_spec.rb'
diff --git a/appraisal/jruby-9.2.rb b/appraisal/jruby-9.2.rb
index 60d0c1ebab6..499f2d27dc3 100644
--- a/appraisal/jruby-9.2.rb
+++ b/appraisal/jruby-9.2.rb
@@ -289,3 +289,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 5.2.1'
+end
diff --git a/appraisal/jruby-9.3.rb b/appraisal/jruby-9.3.rb
index bdc4da0c834..909f16428ee 100644
--- a/appraisal/jruby-9.3.rb
+++ b/appraisal/jruby-9.3.rb
@@ -260,3 +260,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 5.2.1'
+end
diff --git a/appraisal/jruby-9.4.rb b/appraisal/jruby-9.4.rb
index 3e27e129855..2be3709b7c0 100644
--- a/appraisal/jruby-9.4.rb
+++ b/appraisal/jruby-9.4.rb
@@ -166,3 +166,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 6.1.0'
+end
diff --git a/appraisal/ruby-2.5.rb b/appraisal/ruby-2.5.rb
index fe6724405ec..fcacbeb9246 100644
--- a/appraisal/ruby-2.5.rb
+++ b/appraisal/ruby-2.5.rb
@@ -262,3 +262,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 5.2.1'
+end
diff --git a/appraisal/ruby-2.6.rb b/appraisal/ruby-2.6.rb
index 48acdee7559..3e20513b688 100644
--- a/appraisal/ruby-2.6.rb
+++ b/appraisal/ruby-2.6.rb
@@ -263,3 +263,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 5.2.1'
+end
diff --git a/appraisal/ruby-2.7.rb b/appraisal/ruby-2.7.rb
index b6304732c24..4660606429e 100644
--- a/appraisal/ruby-2.7.rb
+++ b/appraisal/ruby-2.7.rb
@@ -264,3 +264,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 5.2.1'
+end
diff --git a/appraisal/ruby-3.0.rb b/appraisal/ruby-3.0.rb
index 942a1a023d4..40e99c0dcea 100644
--- a/appraisal/ruby-3.0.rb
+++ b/appraisal/ruby-3.0.rb
@@ -177,3 +177,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 6.1.0'
+end
diff --git a/appraisal/ruby-3.1.rb b/appraisal/ruby-3.1.rb
index 942a1a023d4..40e99c0dcea 100644
--- a/appraisal/ruby-3.1.rb
+++ b/appraisal/ruby-3.1.rb
@@ -177,3 +177,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 6.1.0'
+end
diff --git a/appraisal/ruby-3.2.rb b/appraisal/ruby-3.2.rb
index 942a1a023d4..40e99c0dcea 100644
--- a/appraisal/ruby-3.2.rb
+++ b/appraisal/ruby-3.2.rb
@@ -177,3 +177,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 6.1.0'
+end
diff --git a/appraisal/ruby-3.3.rb b/appraisal/ruby-3.3.rb
index c9770bd40cf..ec95feba101 100644
--- a/appraisal/ruby-3.3.rb
+++ b/appraisal/ruby-3.3.rb
@@ -179,3 +179,11 @@
 appraise 'core-old' do
   gem 'dogstatsd-ruby', '~> 4'
 end
+
+appraise 'multi-rack-app' do
+  gem 'sinatra', '>= 3'
+  gem 'rack-contrib'
+  gem 'rack-test' # Dev dependencies for testing rack-based code
+  gem 'grape'
+  gem 'rails', '~> 6.1.0'
+end
diff --git a/gemfiles/jruby_9.2_multi_rack_app.gemfile b/gemfiles/jruby_9.2_multi_rack_app.gemfile
new file mode 100644
index 00000000000..c6ad9c076fb
--- /dev/null
+++ b/gemfiles/jruby_9.2_multi_rack_app.gemfile
@@ -0,0 +1,40 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-debugger-jruby"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "yard", "~> 0.9"
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "sinatra"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 5.2.1"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/jruby_9.2_multi_rack_app.gemfile.lock b/gemfiles/jruby_9.2_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..9f3cf167164
--- /dev/null
+++ b/gemfiles/jruby_9.2_multi_rack_app.gemfile.lock
@@ -0,0 +1,311 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailer (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (5.2.8.1)
+      actionview (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      rack (~> 2.0, >= 2.0.8)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.2)
+    actionview (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.3)
+    activejob (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      globalid (>= 0.3.6)
+    activemodel (5.2.8.1)
+      activesupport (= 5.2.8.1)
+    activerecord (5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      arel (>= 9.0)
+    activestorage (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      marcel (~> 1.0.0)
+    activesupport (5.2.8.1)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 0.7, < 2)
+      minitest (~> 5.1)
+      tzinfo (~> 1.1)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    arel (9.0.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6-java)
+    builder (3.2.4)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    debase-ruby_core_source (3.3.1)
+    diff-lcs (1.5.1)
+    digest (3.1.1-java)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-configurable (0.12.1)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.5, >= 0.5.0)
+    dry-container (0.7.2)
+      concurrent-ruby (~> 1.0)
+      dry-configurable (~> 0.1, >= 0.1.3)
+    dry-core (0.6.0)
+      concurrent-ruby (~> 1.0)
+    dry-inflector (0.2.0)
+    dry-logic (1.2.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.5, >= 0.5)
+    dry-types (1.5.1)
+      concurrent-ruby (~> 1.0)
+      dry-container (~> 0.3)
+      dry-core (~> 0.5, >= 0.5)
+      dry-inflector (~> 0.1, >= 0.1.2)
+      dry-logic (~> 1.0, >= 1.0.2)
+    erubi (1.12.0)
+    ffi (1.16.3-java)
+    globalid (1.1.0)
+      activesupport (>= 5.0)
+    grape (1.7.0)
+      activesupport
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    io-wait (0.3.1-java)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0)
+    libddwaf (1.14.0.0.0-java)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.2)
+    minitest (5.15.0)
+    msgpack (1.7.2-java)
+    mustermann (2.0.2)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.2.2)
+      digest
+      net-protocol
+      strscan
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.1.2)
+      io-wait
+      timeout
+    net-smtp (0.3.0)
+      digest
+      net-protocol
+      timeout
+    nio4r (2.7.0-java)
+    nokogiri (1.12.5-java)
+      racc (~> 1.4)
+    os (1.1.4)
+    pimpmychangelog (0.1.3)
+    pry (0.14.2-java)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+      spoon (~> 0.0)
+    pry-debugger-jruby (2.1.1-java)
+      pry (>= 0.13, < 0.15)
+      ruby-debug-base (>= 0.10.4, < 0.12)
+    public_suffix (4.0.7)
+    racc (1.7.3-java)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (2.2.4)
+      rack
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (5.2.8.1)
+      actioncable (= 5.2.8.1)
+      actionmailer (= 5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      activestorage (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      bundler (>= 1.3.0)
+      railties (= 5.2.8.1)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.5.0)
+      loofah (~> 2.19, >= 2.19.1)
+    railties (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      method_source
+      rake (>= 0.8.7)
+      thor (>= 0.19.0, < 2.0)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.3.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    ruby-debug-base (0.11.0-java)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (2.2.4)
+      mustermann (~> 2.0)
+      rack (~> 2.2)
+      rack-protection (= 2.2.4)
+      tilt (~> 2.0)
+    spoon (0.0.6)
+      ffi
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    strscan (3.1.0-java)
+    thor (1.2.2)
+    thread_safe (0.3.6-java)
+    tilt (2.3.0)
+    timeout (0.4.0)
+    tzinfo (1.2.11)
+      thread_safe (~> 0.1)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    websocket-driver (0.7.6-java)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+
+PLATFORMS
+  universal-java-1.8
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-debugger-jruby
+  rack-contrib
+  rack-test
+  rails (~> 5.2.1)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/jruby_9.3_multi_rack_app.gemfile b/gemfiles/jruby_9.3_multi_rack_app.gemfile
new file mode 100644
index 00000000000..1c1fa567d47
--- /dev/null
+++ b/gemfiles/jruby_9.3_multi_rack_app.gemfile
@@ -0,0 +1,44 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-debugger-jruby"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 5.2.1"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/jruby_9.3_multi_rack_app.gemfile.lock b/gemfiles/jruby_9.3_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..108797066cc
--- /dev/null
+++ b/gemfiles/jruby_9.3_multi_rack_app.gemfile.lock
@@ -0,0 +1,343 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailer (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (5.2.8.1)
+      actionview (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      rack (~> 2.0, >= 2.0.8)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.2)
+    actionview (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.3)
+    activejob (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      globalid (>= 0.3.6)
+    activemodel (5.2.8.1)
+      activesupport (= 5.2.8.1)
+    activerecord (5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      arel (>= 9.0)
+    activestorage (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      marcel (~> 1.0.0)
+    activesupport (5.2.8.1)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 0.7, < 2)
+      minitest (~> 5.1)
+      tzinfo (~> 1.1)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    arel (9.0.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6-java)
+    builder (3.2.4)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4-java)
+    debase-ruby_core_source (3.3.1)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-configurable (0.13.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.6)
+    dry-container (0.9.0)
+      concurrent-ruby (~> 1.0)
+      dry-configurable (~> 0.13, >= 0.13.0)
+    dry-core (0.7.1)
+      concurrent-ruby (~> 1.0)
+    dry-inflector (0.2.1)
+    dry-logic (1.2.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.5, >= 0.5)
+    dry-types (1.5.1)
+      concurrent-ruby (~> 1.0)
+      dry-container (~> 0.3)
+      dry-core (~> 0.5, >= 0.5)
+      dry-inflector (~> 0.1, >= 0.1.2)
+      dry-logic (~> 1.0, >= 1.0.2)
+    erubi (1.12.0)
+    ffi (1.16.3-java)
+    globalid (1.1.0)
+      activesupport (>= 5.0)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1-java)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0)
+    libddwaf (1.14.0.0.0-java)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2-java)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.3.7)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0-java)
+    nokogiri (1.13.10-java)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2-java)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+      spoon (~> 0.0)
+    pry-debugger-jruby (2.1.1-java)
+      pry (>= 0.13, < 0.15)
+      ruby-debug-base (>= 0.10.4, < 0.12)
+    public_suffix (5.0.4)
+    racc (1.7.3-java)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (5.2.8.1)
+      actioncable (= 5.2.8.1)
+      actionmailer (= 5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      activestorage (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      bundler (>= 1.3.0)
+      railties (= 5.2.8.1)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.5.0)
+      loofah (~> 2.19, >= 2.19.1)
+    railties (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      method_source
+      rake (>= 0.8.7)
+      thor (>= 0.19.0, < 2.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.4.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.18.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.17.1)
+      rubocop (>= 1.7.0, < 2.0)
+      rubocop-ast (>= 0.4.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-debug-base (0.11.0-java)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    spoon (0.0.6)
+      ffi
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    thread_safe (0.3.6-java)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (1.2.11)
+      thread_safe (~> 0.1)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    websocket-driver (0.7.6-java)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+
+PLATFORMS
+  universal-java-11
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-debugger-jruby
+  rack-contrib
+  rack-test
+  rails (~> 5.2.1)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/jruby_9.4_multi_rack_app.gemfile b/gemfiles/jruby_9.4_multi_rack_app.gemfile
new file mode 100644
index 00000000000..497f65f4870
--- /dev/null
+++ b/gemfiles/jruby_9.4_multi_rack_app.gemfile
@@ -0,0 +1,45 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-debugger-jruby"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "webrick", ">= 1.7.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 6.1.0"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/jruby_9.4_multi_rack_app.gemfile.lock b/gemfiles/jruby_9.4_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..54f206722bb
--- /dev/null
+++ b/gemfiles/jruby_9.4_multi_rack_app.gemfile.lock
@@ -0,0 +1,362 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailbox (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (>= 2.7.1)
+    actionmailer (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (6.1.7.6)
+      actionview (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      rack (~> 2.0, >= 2.0.9)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actiontext (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nokogiri (>= 1.8.5)
+    actionview (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activejob (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      globalid (>= 0.3.6)
+    activemodel (6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activerecord (6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activestorage (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      marcel (~> 1.0)
+      mini_mime (>= 1.1.0)
+    activesupport (6.1.7.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6-java)
+    builder (3.2.4)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4-java)
+    debase-ruby_core_source (3.3.1)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-core (1.0.1)
+      concurrent-ruby (~> 1.0)
+      zeitwerk (~> 2.6)
+    dry-inflector (1.0.0)
+    dry-logic (1.5.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0, < 2)
+      zeitwerk (~> 2.6)
+    dry-types (1.7.2)
+      bigdecimal (~> 3.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0)
+      dry-inflector (~> 1.0)
+      dry-logic (~> 1.4)
+      zeitwerk (~> 2.6)
+    erubi (1.12.0)
+    ffi (1.16.3-java)
+    globalid (1.2.1)
+      activesupport (>= 6.1)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1-java)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0)
+    libddwaf (1.14.0.0.0-java)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2-java)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.4.10)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0-java)
+    nokogiri (1.16.2-java)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2-java)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+      spoon (~> 0.0)
+    pry-debugger-jruby (2.1.1-java)
+      pry (>= 0.13, < 0.15)
+      ruby-debug-base (>= 0.10.4, < 0.12)
+    public_suffix (5.0.4)
+    racc (1.7.3-java)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (6.1.7.6)
+      actioncable (= 6.1.7.6)
+      actionmailbox (= 6.1.7.6)
+      actionmailer (= 6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actiontext (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      bundler (>= 1.15.0)
+      railties (= 6.1.7.6)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.5.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.20.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.20.2)
+      rubocop (>= 1.48.1, < 2.0)
+      rubocop-ast (>= 1.30.0, < 2.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-debug-base (0.11.0-java)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    spoon (0.0.6)
+      ffi
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    webrick (1.8.1)
+    websocket-driver (0.7.6-java)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+    zeitwerk (2.6.13)
+
+PLATFORMS
+  universal-java-11
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-debugger-jruby
+  rack-contrib
+  rack-test
+  rails (~> 6.1.0)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  webrick (>= 1.7.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_2.5_multi_rack_app.gemfile b/gemfiles/ruby_2.5_multi_rack_app.gemfile
new file mode 100644
index 00000000000..29e9626adaf
--- /dev/null
+++ b/gemfiles/ruby_2.5_multi_rack_app.gemfile
@@ -0,0 +1,44 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-nav"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "yard", "~> 0.9"
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1", "< 3.19.2"]
+gem "sinatra"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 5.2.1"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_2.5_multi_rack_app.gemfile.lock b/gemfiles/ruby_2.5_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..c9a78ed615d
--- /dev/null
+++ b/gemfiles/ruby_2.5_multi_rack_app.gemfile.lock
@@ -0,0 +1,328 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailer (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (5.2.8.1)
+      actionview (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      rack (~> 2.0, >= 2.0.8)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.2)
+    actionview (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.3)
+    activejob (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      globalid (>= 0.3.6)
+    activemodel (5.2.8.1)
+      activesupport (= 5.2.8.1)
+    activerecord (5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      arel (>= 9.0)
+    activestorage (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      marcel (~> 1.0.0)
+    activesupport (5.2.8.1)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 0.7, < 2)
+      minitest (~> 5.1)
+      tzinfo (~> 1.1)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    arel (9.0.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (0.8.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    digest (3.1.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-configurable (0.12.1)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.5, >= 0.5.0)
+    dry-container (0.7.2)
+      concurrent-ruby (~> 1.0)
+      dry-configurable (~> 0.1, >= 0.1.3)
+    dry-core (0.6.0)
+      concurrent-ruby (~> 1.0)
+    dry-inflector (0.2.0)
+    dry-logic (1.2.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.5, >= 0.5)
+    dry-types (1.5.1)
+      concurrent-ruby (~> 1.0)
+      dry-container (~> 0.3)
+      dry-core (~> 0.5, >= 0.5)
+      dry-inflector (~> 0.1, >= 0.1.2)
+      dry-logic (~> 1.0, >= 1.0.2)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.1.0)
+      activesupport (>= 5.0)
+    google-protobuf (3.19.1)
+    google-protobuf (3.19.1-x86_64-linux)
+    grape (1.7.0)
+      activesupport
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    io-wait (0.3.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-aarch64-linux)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-aarch64-linux)
+      ffi (~> 1.0)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.2)
+    mini_portile2 (2.6.1)
+    minitest (5.15.0)
+    msgpack (1.7.2)
+    mustermann (2.0.2)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.2.2)
+      digest
+      net-protocol
+      strscan
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.1.2)
+      io-wait
+      timeout
+    net-smtp (0.3.0)
+      digest
+      net-protocol
+      timeout
+    nio4r (2.7.0)
+    nokogiri (1.12.5)
+      mini_portile2 (~> 2.6.1)
+      racc (~> 1.4)
+    nokogiri (1.12.5-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-nav (1.0.0)
+      pry (>= 0.9.10, < 0.15)
+    pry-stack_explorer (0.4.13)
+      binding_of_caller (~> 0.7)
+      pry (~> 0.13)
+    public_suffix (4.0.7)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (2.2.4)
+      rack
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (5.2.8.1)
+      actioncable (= 5.2.8.1)
+      actionmailer (= 5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      activestorage (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      bundler (>= 1.3.0)
+      railties (= 5.2.8.1)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.5.0)
+      loofah (~> 2.19, >= 2.19.1)
+    railties (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      method_source
+      rake (>= 0.8.7)
+      thor (>= 0.19.0, < 2.0)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.3.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (2.2.4)
+      mustermann (~> 2.0)
+      rack (~> 2.2)
+      rack-protection (= 2.2.4)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    strscan (3.1.0)
+    thor (1.2.2)
+    thread_safe (0.3.6)
+    tilt (2.3.0)
+    timeout (0.4.0)
+    tzinfo (1.2.11)
+      thread_safe (~> 0.1)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, < 3.19.2, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-nav
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 5.2.1)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_2.6_multi_rack_app.gemfile b/gemfiles/ruby_2.6_multi_rack_app.gemfile
new file mode 100644
index 00000000000..e63f93f08f3
--- /dev/null
+++ b/gemfiles/ruby_2.6_multi_rack_app.gemfile
@@ -0,0 +1,48 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-byebug"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1", "< 3.19.2"]
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 5.2.1"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_2.6_multi_rack_app.gemfile.lock b/gemfiles/ruby_2.6_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..49044e453d5
--- /dev/null
+++ b/gemfiles/ruby_2.6_multi_rack_app.gemfile.lock
@@ -0,0 +1,360 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailer (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (5.2.8.1)
+      actionview (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      rack (~> 2.0, >= 2.0.8)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.2)
+    actionview (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.3)
+    activejob (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      globalid (>= 0.3.6)
+    activemodel (5.2.8.1)
+      activesupport (= 5.2.8.1)
+    activerecord (5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      arel (>= 9.0)
+    activestorage (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      marcel (~> 1.0.0)
+    activesupport (5.2.8.1)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 0.7, < 2)
+      minitest (~> 5.1)
+      tzinfo (~> 1.1)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    arel (9.0.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (1.0.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    byebug (11.1.3)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4)
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-configurable (0.13.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.6)
+    dry-container (0.9.0)
+      concurrent-ruby (~> 1.0)
+      dry-configurable (~> 0.13, >= 0.13.0)
+    dry-core (0.7.1)
+      concurrent-ruby (~> 1.0)
+    dry-inflector (0.2.1)
+    dry-logic (1.2.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 0.5, >= 0.5)
+    dry-types (1.5.1)
+      concurrent-ruby (~> 1.0)
+      dry-container (~> 0.3)
+      dry-core (~> 0.5, >= 0.5)
+      dry-inflector (~> 0.1, >= 0.1.2)
+      dry-logic (~> 1.0, >= 1.0.2)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.1.0)
+      activesupport (>= 5.0)
+    google-protobuf (3.19.1)
+    google-protobuf (3.19.1-x86_64-linux)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-aarch64-linux)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-aarch64-linux)
+      ffi (~> 1.0)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.3.7)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0)
+    nokogiri (1.13.10-aarch64-linux)
+      racc (~> 1.4)
+    nokogiri (1.13.10-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-byebug (3.8.0)
+      byebug (~> 11.0)
+      pry (~> 0.10)
+    pry-stack_explorer (0.6.1)
+      binding_of_caller (~> 1.0)
+      pry (~> 0.13)
+    public_suffix (5.0.4)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (5.2.8.1)
+      actioncable (= 5.2.8.1)
+      actionmailer (= 5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      activestorage (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      bundler (>= 1.3.0)
+      railties (= 5.2.8.1)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.5.0)
+      loofah (~> 2.19, >= 2.19.1)
+    railties (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      method_source
+      rake (>= 0.8.7)
+      thor (>= 0.19.0, < 2.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.4.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.18.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.17.1)
+      rubocop (>= 1.7.0, < 2.0)
+      rubocop-ast (>= 0.4.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    thread_safe (0.3.6)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (1.2.11)
+      thread_safe (~> 0.1)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, < 3.19.2, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-byebug
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 5.2.1)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_2.7_multi_rack_app.gemfile b/gemfiles/ruby_2.7_multi_rack_app.gemfile
new file mode 100644
index 00000000000..6a5ceddeba5
--- /dev/null
+++ b/gemfiles/ruby_2.7_multi_rack_app.gemfile
@@ -0,0 +1,48 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-byebug"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1"]
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 5.2.1"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_2.7_multi_rack_app.gemfile.lock b/gemfiles/ruby_2.7_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..3aaf9df480d
--- /dev/null
+++ b/gemfiles/ruby_2.7_multi_rack_app.gemfile.lock
@@ -0,0 +1,358 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailer (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (5.2.8.1)
+      actionview (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      rack (~> 2.0, >= 2.0.8)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.2)
+    actionview (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.0.3)
+    activejob (5.2.8.1)
+      activesupport (= 5.2.8.1)
+      globalid (>= 0.3.6)
+    activemodel (5.2.8.1)
+      activesupport (= 5.2.8.1)
+    activerecord (5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      arel (>= 9.0)
+    activestorage (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      marcel (~> 1.0.0)
+    activesupport (5.2.8.1)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 0.7, < 2)
+      minitest (~> 5.1)
+      tzinfo (~> 1.1)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    arel (9.0.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (1.0.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    byebug (11.1.3)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4)
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-core (1.0.0)
+      concurrent-ruby (~> 1.0)
+      zeitwerk (~> 2.6)
+    dry-inflector (1.0.0)
+    dry-logic (1.5.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0, < 2)
+      zeitwerk (~> 2.6)
+    dry-types (1.7.1)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0)
+      dry-inflector (~> 1.0)
+      dry-logic (~> 1.4)
+      zeitwerk (~> 2.6)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.1.0)
+      activesupport (>= 5.0)
+    google-protobuf (3.25.2-aarch64-linux)
+    google-protobuf (3.25.2-x86_64-linux)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-aarch64-linux)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-aarch64-linux)
+      ffi (~> 1.0)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.4.10)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0)
+    nokogiri (1.15.5-aarch64-linux)
+      racc (~> 1.4)
+    nokogiri (1.15.5-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-byebug (3.10.1)
+      byebug (~> 11.0)
+      pry (>= 0.13, < 0.15)
+    pry-stack_explorer (0.6.1)
+      binding_of_caller (~> 1.0)
+      pry (~> 0.13)
+    public_suffix (5.0.4)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (5.2.8.1)
+      actioncable (= 5.2.8.1)
+      actionmailer (= 5.2.8.1)
+      actionpack (= 5.2.8.1)
+      actionview (= 5.2.8.1)
+      activejob (= 5.2.8.1)
+      activemodel (= 5.2.8.1)
+      activerecord (= 5.2.8.1)
+      activestorage (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      bundler (>= 1.3.0)
+      railties (= 5.2.8.1)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (5.2.8.1)
+      actionpack (= 5.2.8.1)
+      activesupport (= 5.2.8.1)
+      method_source
+      rake (>= 0.8.7)
+      thor (>= 0.19.0, < 2.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.5.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.20.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.20.2)
+      rubocop (>= 1.48.1, < 2.0)
+      rubocop-ast (>= 1.30.0, < 2.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    thread_safe (0.3.6)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (1.2.11)
+      thread_safe (~> 0.1)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+    zeitwerk (2.6.13)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-byebug
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 5.2.1)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_3.0_multi_rack_app.gemfile b/gemfiles/ruby_3.0_multi_rack_app.gemfile
new file mode 100644
index 00000000000..c3efafe49a7
--- /dev/null
+++ b/gemfiles/ruby_3.0_multi_rack_app.gemfile
@@ -0,0 +1,49 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-byebug"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "webrick", ">= 1.7.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1"]
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 6.1.0"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_3.0_multi_rack_app.gemfile.lock b/gemfiles/ruby_3.0_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..0d461b48119
--- /dev/null
+++ b/gemfiles/ruby_3.0_multi_rack_app.gemfile.lock
@@ -0,0 +1,379 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailbox (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (>= 2.7.1)
+    actionmailer (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (6.1.7.6)
+      actionview (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      rack (~> 2.0, >= 2.0.9)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actiontext (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nokogiri (>= 1.8.5)
+    actionview (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activejob (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      globalid (>= 0.3.6)
+    activemodel (6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activerecord (6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activestorage (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      marcel (~> 1.0)
+      mini_mime (>= 1.1.0)
+    activesupport (6.1.7.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (1.0.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    byebug (11.1.3)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4)
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-core (1.0.1)
+      concurrent-ruby (~> 1.0)
+      zeitwerk (~> 2.6)
+    dry-inflector (1.0.0)
+    dry-logic (1.5.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0, < 2)
+      zeitwerk (~> 2.6)
+    dry-types (1.7.2)
+      bigdecimal (~> 3.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0)
+      dry-inflector (~> 1.0)
+      dry-logic (~> 1.4)
+      zeitwerk (~> 2.6)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.2.1)
+      activesupport (>= 6.1)
+    google-protobuf (3.25.2-aarch64-linux)
+    google-protobuf (3.25.2-x86_64-linux)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-aarch64-linux)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-aarch64-linux)
+      ffi (~> 1.0)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.4.10)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0)
+    nokogiri (1.16.2-aarch64-linux)
+      racc (~> 1.4)
+    nokogiri (1.16.2-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-byebug (3.10.1)
+      byebug (~> 11.0)
+      pry (>= 0.13, < 0.15)
+    pry-stack_explorer (0.6.1)
+      binding_of_caller (~> 1.0)
+      pry (~> 0.13)
+    public_suffix (5.0.4)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (6.1.7.6)
+      actioncable (= 6.1.7.6)
+      actionmailbox (= 6.1.7.6)
+      actionmailer (= 6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actiontext (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      bundler (>= 1.15.0)
+      railties (= 6.1.7.6)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.5.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.20.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.20.2)
+      rubocop (>= 1.48.1, < 2.0)
+      rubocop-ast (>= 1.30.0, < 2.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    webrick (1.8.1)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+    zeitwerk (2.6.13)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-byebug
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 6.1.0)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  webrick (>= 1.7.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_3.1_multi_rack_app.gemfile b/gemfiles/ruby_3.1_multi_rack_app.gemfile
new file mode 100644
index 00000000000..c3efafe49a7
--- /dev/null
+++ b/gemfiles/ruby_3.1_multi_rack_app.gemfile
@@ -0,0 +1,49 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-byebug"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "webrick", ">= 1.7.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1"]
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 6.1.0"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_3.1_multi_rack_app.gemfile.lock b/gemfiles/ruby_3.1_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..ecd61e5927d
--- /dev/null
+++ b/gemfiles/ruby_3.1_multi_rack_app.gemfile.lock
@@ -0,0 +1,376 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailbox (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (>= 2.7.1)
+    actionmailer (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (6.1.7.6)
+      actionview (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      rack (~> 2.0, >= 2.0.9)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actiontext (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nokogiri (>= 1.8.5)
+    actionview (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activejob (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      globalid (>= 0.3.6)
+    activemodel (6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activerecord (6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activestorage (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      marcel (~> 1.0)
+      mini_mime (>= 1.1.0)
+    activesupport (6.1.7.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (1.0.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    byebug (11.1.3)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4)
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-core (1.0.1)
+      concurrent-ruby (~> 1.0)
+      zeitwerk (~> 2.6)
+    dry-inflector (1.0.0)
+    dry-logic (1.5.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0, < 2)
+      zeitwerk (~> 2.6)
+    dry-types (1.7.2)
+      bigdecimal (~> 3.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0)
+      dry-inflector (~> 1.0)
+      dry-logic (~> 1.4)
+      zeitwerk (~> 2.6)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.2.1)
+      activesupport (>= 6.1)
+    google-protobuf (3.25.2-aarch64-linux)
+    google-protobuf (3.25.2-x86_64-linux)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.4.10)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0)
+    nokogiri (1.16.2-aarch64-linux)
+      racc (~> 1.4)
+    nokogiri (1.16.2-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-byebug (3.10.1)
+      byebug (~> 11.0)
+      pry (>= 0.13, < 0.15)
+    pry-stack_explorer (0.6.1)
+      binding_of_caller (~> 1.0)
+      pry (~> 0.13)
+    public_suffix (5.0.4)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (6.1.7.6)
+      actioncable (= 6.1.7.6)
+      actionmailbox (= 6.1.7.6)
+      actionmailer (= 6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actiontext (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      bundler (>= 1.15.0)
+      railties (= 6.1.7.6)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.5.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.20.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.20.2)
+      rubocop (>= 1.48.1, < 2.0)
+      rubocop-ast (>= 1.30.0, < 2.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    webrick (1.8.1)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+    zeitwerk (2.6.12)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-byebug
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 6.1.0)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  webrick (>= 1.7.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_3.2_multi_rack_app.gemfile b/gemfiles/ruby_3.2_multi_rack_app.gemfile
new file mode 100644
index 00000000000..d5deb903244
--- /dev/null
+++ b/gemfiles/ruby_3.2_multi_rack_app.gemfile
@@ -0,0 +1,48 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "webrick", ">= 1.7.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1"]
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 6.1.0"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_3.2_multi_rack_app.gemfile.lock b/gemfiles/ruby_3.2_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..1901570110e
--- /dev/null
+++ b/gemfiles/ruby_3.2_multi_rack_app.gemfile.lock
@@ -0,0 +1,374 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailbox (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (>= 2.7.1)
+    actionmailer (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (6.1.7.6)
+      actionview (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      rack (~> 2.0, >= 2.0.9)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actiontext (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nokogiri (>= 1.8.5)
+    actionview (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activejob (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      globalid (>= 0.3.6)
+    activemodel (6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activerecord (6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activestorage (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      marcel (~> 1.0)
+      mini_mime (>= 1.1.0)
+    activesupport (6.1.7.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (1.0.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4)
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-core (1.0.1)
+      concurrent-ruby (~> 1.0)
+      zeitwerk (~> 2.6)
+    dry-inflector (1.0.0)
+    dry-logic (1.5.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0, < 2)
+      zeitwerk (~> 2.6)
+    dry-types (1.7.2)
+      bigdecimal (~> 3.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0)
+      dry-inflector (~> 1.0)
+      dry-logic (~> 1.4)
+      zeitwerk (~> 2.6)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.2.1)
+      activesupport (>= 6.1)
+    google-protobuf (3.25.2-aarch64-linux)
+    google-protobuf (3.25.2-x86_64-linux)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-aarch64-linux)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-aarch64-linux)
+      ffi (~> 1.0)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.4.10)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0)
+    nokogiri (1.16.2-aarch64-linux)
+      racc (~> 1.4)
+    nokogiri (1.16.2-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-stack_explorer (0.6.1)
+      binding_of_caller (~> 1.0)
+      pry (~> 0.13)
+    public_suffix (5.0.4)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (6.1.7.6)
+      actioncable (= 6.1.7.6)
+      actionmailbox (= 6.1.7.6)
+      actionmailer (= 6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actiontext (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      bundler (>= 1.15.0)
+      railties (= 6.1.7.6)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.5.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.20.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.20.2)
+      rubocop (>= 1.48.1, < 2.0)
+      rubocop-ast (>= 1.30.0, < 2.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    webrick (1.8.1)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+    zeitwerk (2.6.13)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 6.1.0)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  webrick (>= 1.7.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/gemfiles/ruby_3.3_multi_rack_app.gemfile b/gemfiles/ruby_3.3_multi_rack_app.gemfile
new file mode 100644
index 00000000000..d5deb903244
--- /dev/null
+++ b/gemfiles/ruby_3.3_multi_rack_app.gemfile
@@ -0,0 +1,48 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "appraisal", "~> 2.4.0"
+gem "benchmark-ips", "~> 2.8"
+gem "benchmark-memory", "< 0.2"
+gem "builder"
+gem "climate_control", "~> 0.2.0"
+gem "concurrent-ruby"
+gem "extlz4", "~> 0.3", ">= 0.3.3"
+gem "json-schema", "< 3"
+gem "memory_profiler", "~> 0.9"
+gem "os", "~> 1.1"
+gem "pimpmychangelog", ">= 0.1.2"
+gem "pry"
+gem "pry-stack_explorer"
+gem "rake", ">= 10.5"
+gem "rake-compiler", "~> 1.1", ">= 1.1.1"
+gem "redcarpet", "~> 3.4"
+gem "rspec", "~> 3.12"
+gem "rspec-collection_matchers", "~> 1.1"
+gem "rspec-wait", "~> 0"
+gem "rspec_junit_formatter", ">= 0.5.1"
+gem "rspec_n", "~> 1.3"
+gem "simplecov", git: "https://github.com/DataDog/simplecov", ref: "3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db"
+gem "simplecov-cobertura", "~> 2.1.0"
+gem "warning", "~> 1"
+gem "webmock", ">= 3.10.0"
+gem "webrick", ">= 1.7.0"
+gem "yard", "~> 0.9"
+gem "rubocop", "~> 1.50.0", require: false
+gem "rubocop-packaging", "~> 0.5.2", require: false
+gem "rubocop-performance", "~> 1.9", require: false
+gem "rubocop-rspec", ["~> 2.20", "< 2.21"], require: false
+gem "dogstatsd-ruby", ">= 3.3.0", "!= 5.0.0", "!= 5.0.1", "!= 5.1.0"
+gem "google-protobuf", ["~> 3.0", "!= 3.7.0", "!= 3.7.1"]
+gem "sinatra", ">= 3"
+gem "rack-contrib"
+gem "rack-test"
+gem "grape"
+gem "rails", "~> 6.1.0"
+
+group :check do
+
+end
+
+gemspec path: "../"
diff --git a/gemfiles/ruby_3.3_multi_rack_app.gemfile.lock b/gemfiles/ruby_3.3_multi_rack_app.gemfile.lock
new file mode 100644
index 00000000000..d8ff8e4c3f2
--- /dev/null
+++ b/gemfiles/ruby_3.3_multi_rack_app.gemfile.lock
@@ -0,0 +1,373 @@
+GIT
+  remote: https://github.com/DataDog/simplecov
+  revision: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  ref: 3bb6b7ee58bf4b1954ca205f50dd44d6f41c57db
+  specs:
+    simplecov (0.21.2)
+      docile (~> 1.1)
+      simplecov-html (~> 0.11)
+      simplecov_json_formatter (~> 0.1)
+
+PATH
+  remote: ..
+  specs:
+    ddtrace (1.20.0)
+      datadog-ci (~> 0.7.0)
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 5.0.0.1.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
+
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actioncable (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nio4r (~> 2.0)
+      websocket-driver (>= 0.6.1)
+    actionmailbox (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (>= 2.7.1)
+    actionmailer (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      mail (~> 2.5, >= 2.5.4)
+      rails-dom-testing (~> 2.0)
+    actionpack (6.1.7.6)
+      actionview (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      rack (~> 2.0, >= 2.0.9)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actiontext (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      nokogiri (>= 1.8.5)
+    actionview (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activejob (6.1.7.6)
+      activesupport (= 6.1.7.6)
+      globalid (>= 0.3.6)
+    activemodel (6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activerecord (6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+    activestorage (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      marcel (~> 1.0)
+      mini_mime (>= 1.1.0)
+    activesupport (6.1.7.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
+    addressable (2.8.6)
+      public_suffix (>= 2.0.2, < 6.0)
+    appraisal (2.4.1)
+      bundler
+      rake
+      thor (>= 0.14.0)
+    ast (2.4.2)
+    base64 (0.2.0)
+    benchmark-ips (2.13.0)
+    benchmark-memory (0.1.2)
+      memory_profiler (~> 0.9)
+    bigdecimal (3.1.6)
+    binding_of_caller (1.0.0)
+      debug_inspector (>= 0.0.1)
+    builder (3.2.4)
+    climate_control (0.2.0)
+    coderay (1.1.3)
+    colorize (0.8.1)
+    concurrent-ruby (1.2.3)
+    crack (0.4.6)
+      bigdecimal
+      rexml
+    crass (1.0.6)
+    cri (2.15.11)
+    datadog-ci (0.7.0)
+      msgpack
+    date (3.3.4)
+    debase-ruby_core_source (3.3.1)
+    debug_inspector (1.2.0)
+    diff-lcs (1.5.1)
+    docile (1.4.0)
+    dogstatsd-ruby (5.6.1)
+    dry-core (1.0.1)
+      concurrent-ruby (~> 1.0)
+      zeitwerk (~> 2.6)
+    dry-inflector (1.0.0)
+    dry-logic (1.5.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0, < 2)
+      zeitwerk (~> 2.6)
+    dry-types (1.7.2)
+      bigdecimal (~> 3.0)
+      concurrent-ruby (~> 1.0)
+      dry-core (~> 1.0)
+      dry-inflector (~> 1.0)
+      dry-logic (~> 1.4)
+      zeitwerk (~> 2.6)
+    erubi (1.12.0)
+    extlz4 (0.3.4)
+    ffi (1.16.3)
+    globalid (1.2.1)
+      activesupport (>= 6.1)
+    google-protobuf (3.25.2)
+    grape (2.0.0)
+      activesupport (>= 5)
+      builder
+      dry-types (>= 1.1)
+      mustermann-grape (~> 1.0.0)
+      rack (>= 1.3.0)
+      rack-accept
+    hashdiff (1.1.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    json (2.7.1)
+    json-schema (2.8.1)
+      addressable (>= 2.4)
+    libdatadog (5.0.0.1.0-aarch64-linux)
+    libdatadog (5.0.0.1.0-x86_64-linux)
+    libddwaf (1.14.0.0.0-aarch64-linux)
+      ffi (~> 1.0)
+    libddwaf (1.14.0.0.0-x86_64-linux)
+      ffi (~> 1.0)
+    loofah (2.22.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    mail (2.8.1)
+      mini_mime (>= 0.1.1)
+      net-imap
+      net-pop
+      net-smtp
+    marcel (1.0.2)
+    memory_profiler (0.9.14)
+    method_source (1.0.0)
+    mini_mime (1.1.5)
+    minitest (5.22.0)
+    msgpack (1.7.2)
+    mustermann (3.0.0)
+      ruby2_keywords (~> 0.0.1)
+    mustermann-grape (1.0.2)
+      mustermann (>= 1.0.0)
+    net-imap (0.4.10)
+      date
+      net-protocol
+    net-pop (0.1.2)
+      net-protocol
+    net-protocol (0.2.2)
+      timeout
+    net-smtp (0.4.0.1)
+      net-protocol
+    nio4r (2.7.0)
+    nokogiri (1.16.2-aarch64-linux)
+      racc (~> 1.4)
+    nokogiri (1.16.2-x86_64-linux)
+      racc (~> 1.4)
+    os (1.1.4)
+    parallel (1.24.0)
+    parser (3.3.0.5)
+      ast (~> 2.4.1)
+      racc
+    pimpmychangelog (0.1.3)
+    pry (0.14.2)
+      coderay (~> 1.1)
+      method_source (~> 1.0)
+    pry-stack_explorer (0.6.1)
+      binding_of_caller (~> 1.0)
+      pry (~> 0.13)
+    public_suffix (5.0.4)
+    racc (1.7.3)
+    rack (2.2.8)
+    rack-accept (0.4.5)
+      rack (>= 0.4)
+    rack-contrib (2.4.0)
+      rack (< 4)
+    rack-protection (3.2.0)
+      base64 (>= 0.1.0)
+      rack (~> 2.2, >= 2.2.4)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails (6.1.7.6)
+      actioncable (= 6.1.7.6)
+      actionmailbox (= 6.1.7.6)
+      actionmailer (= 6.1.7.6)
+      actionpack (= 6.1.7.6)
+      actiontext (= 6.1.7.6)
+      actionview (= 6.1.7.6)
+      activejob (= 6.1.7.6)
+      activemodel (= 6.1.7.6)
+      activerecord (= 6.1.7.6)
+      activestorage (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      bundler (>= 1.15.0)
+      railties (= 6.1.7.6)
+      sprockets-rails (>= 2.0.0)
+    rails-dom-testing (2.2.0)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (6.1.7.6)
+      actionpack (= 6.1.7.6)
+      activesupport (= 6.1.7.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+    rainbow (3.1.1)
+    rake (13.1.0)
+    rake-compiler (1.2.7)
+      rake
+    redcarpet (3.6.0)
+    regexp_parser (2.9.0)
+    rexml (3.2.6)
+    rspec (3.13.0)
+      rspec-core (~> 3.13.0)
+      rspec-expectations (~> 3.13.0)
+      rspec-mocks (~> 3.13.0)
+    rspec-collection_matchers (1.2.1)
+      rspec-expectations (>= 2.99.0.beta1)
+    rspec-core (3.13.0)
+      rspec-support (~> 3.13.0)
+    rspec-expectations (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-mocks (3.13.0)
+      diff-lcs (>= 1.2.0, < 2.0)
+      rspec-support (~> 3.13.0)
+    rspec-support (3.13.0)
+    rspec-wait (0.0.9)
+      rspec (>= 3, < 4)
+    rspec_junit_formatter (0.6.0)
+      rspec-core (>= 2, < 4, != 2.12.0)
+    rspec_n (1.5.0)
+      colorize (~> 0.8.0)
+      cri (~> 2.15.3)
+    rubocop (1.50.2)
+      json (~> 2.3)
+      parallel (~> 1.10)
+      parser (>= 3.2.0.0)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.30.0)
+      parser (>= 3.2.1.0)
+    rubocop-capybara (2.20.0)
+      rubocop (~> 1.41)
+    rubocop-packaging (0.5.2)
+      rubocop (>= 1.33, < 2.0)
+    rubocop-performance (1.20.2)
+      rubocop (>= 1.48.1, < 2.0)
+      rubocop-ast (>= 1.30.0, < 2.0)
+    rubocop-rspec (2.20.0)
+      rubocop (~> 1.33)
+      rubocop-capybara (~> 2.17)
+    ruby-progressbar (1.13.0)
+    ruby2_keywords (0.0.5)
+    simplecov-cobertura (2.1.0)
+      rexml
+      simplecov (~> 0.19)
+    simplecov-html (0.12.3)
+    simplecov_json_formatter (0.1.4)
+    sinatra (3.2.0)
+      mustermann (~> 3.0)
+      rack (~> 2.2, >= 2.2.4)
+      rack-protection (= 3.2.0)
+      tilt (~> 2.0)
+    sprockets (4.2.1)
+      concurrent-ruby (~> 1.0)
+      rack (>= 2.2.4, < 4)
+    sprockets-rails (3.4.2)
+      actionpack (>= 5.2)
+      activesupport (>= 5.2)
+      sprockets (>= 3.0.0)
+    thor (1.3.0)
+    tilt (2.3.0)
+    timeout (0.4.1)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    unicode-display_width (2.5.0)
+    warning (1.3.0)
+    webmock (3.19.1)
+      addressable (>= 2.8.0)
+      crack (>= 0.3.2)
+      hashdiff (>= 0.4.0, < 2.0.0)
+    webrick (1.8.1)
+    websocket-driver (0.7.6)
+      websocket-extensions (>= 0.1.0)
+    websocket-extensions (0.1.5)
+    yard (0.9.34)
+    zeitwerk (2.6.13)
+
+PLATFORMS
+  aarch64-linux
+  x86_64-linux
+
+DEPENDENCIES
+  appraisal (~> 2.4.0)
+  benchmark-ips (~> 2.8)
+  benchmark-memory (< 0.2)
+  builder
+  climate_control (~> 0.2.0)
+  concurrent-ruby
+  ddtrace!
+  dogstatsd-ruby (>= 3.3.0, != 5.1.0, != 5.0.1, != 5.0.0)
+  extlz4 (~> 0.3, >= 0.3.3)
+  google-protobuf (~> 3.0, != 3.7.1, != 3.7.0)
+  grape
+  json-schema (< 3)
+  memory_profiler (~> 0.9)
+  os (~> 1.1)
+  pimpmychangelog (>= 0.1.2)
+  pry
+  pry-stack_explorer
+  rack-contrib
+  rack-test
+  rails (~> 6.1.0)
+  rake (>= 10.5)
+  rake-compiler (~> 1.1, >= 1.1.1)
+  redcarpet (~> 3.4)
+  rspec (~> 3.12)
+  rspec-collection_matchers (~> 1.1)
+  rspec-wait (~> 0)
+  rspec_junit_formatter (>= 0.5.1)
+  rspec_n (~> 1.3)
+  rubocop (~> 1.50.0)
+  rubocop-packaging (~> 0.5.2)
+  rubocop-performance (~> 1.9)
+  rubocop-rspec (~> 2.20, < 2.21)
+  simplecov!
+  simplecov-cobertura (~> 2.1.0)
+  sinatra (>= 3)
+  warning (~> 1)
+  webmock (>= 3.10.0)
+  webrick (>= 1.7.0)
+  yard (~> 0.9)
+
+BUNDLED WITH
+   2.3.26
diff --git a/lib/datadog/tracing/contrib/grape/endpoint.rb b/lib/datadog/tracing/contrib/grape/endpoint.rb
index 3231b853074..3081660ccfb 100644
--- a/lib/datadog/tracing/contrib/grape/endpoint.rb
+++ b/lib/datadog/tracing/contrib/grape/endpoint.rb
@@ -94,6 +94,8 @@ def endpoint_run(name, start, finish, id, payload)
 
                 span.set_error(payload[:exception_object]) if exception_is_error?(payload[:exception_object])
 
+                integration_route = endpoint.env['grape.routing_args'][:route_info].pattern.origin
+
                 # override the current span with this notification values
                 span.set_tag(Ext::TAG_ROUTE_ENDPOINT, api_view) unless api_view.nil?
                 span.set_tag(Ext::TAG_ROUTE_PATH, path)
@@ -101,6 +103,9 @@ def endpoint_run(name, start, finish, id, payload)
 
                 span.set_tag(Tracing::Metadata::Ext::HTTP::TAG_METHOD, request_method)
                 span.set_tag(Tracing::Metadata::Ext::HTTP::TAG_URL, path)
+
+                trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE, integration_route)
+                trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH, endpoint.env['SCRIPT_NAME'])
               ensure
                 span.start(start)
                 span.finish(finish)
diff --git a/lib/datadog/tracing/contrib/rack/middlewares.rb b/lib/datadog/tracing/contrib/rack/middlewares.rb
index 59ce44bde78..d2811a6517a 100644
--- a/lib/datadog/tracing/contrib/rack/middlewares.rb
+++ b/lib/datadog/tracing/contrib/rack/middlewares.rb
@@ -66,6 +66,10 @@ def compute_queue_time(env)
             end
           end
 
+          # rubocop:disable Metrics/CyclomaticComplexity
+          # rubocop:disable Metrics/PerceivedComplexity
+          # rubocop:disable Metrics/MethodLength
+          # rubocop:disable Metrics/AbcSize
           def call(env)
             # Find out if this is rack within rack
             previous_request_span = env[Ext::RACK_ENV_REQUEST_SPAN]
@@ -107,6 +111,30 @@ def call(env)
 
             # call the rest of the stack
             status, headers, response = @app.call(env)
+
+            if status != 404 && (last_route = request_trace.get_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE))
+              last_script_name = request_trace.get_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH)
+
+              # If the last_script_name is empty but the env['SCRIPT_NAME'] is NOT empty
+              # then the current rack request was not routed and must be accounted for
+              # which only happens in pure nested rack requests i.e /rack/rack/hello/world
+              #
+              # To account for the unaccounted nested rack requests of /rack/hello/world,
+              # we use 'PATH_INFO knowing that rack cannot have named parameters
+              if last_script_name == '' && env['SCRIPT_NAME'] != ''
+                last_script_name = last_route
+                last_route = env['PATH_INFO']
+              end
+
+              # Clear the route and route path tags from the request trace to avoid possibility of misplacement
+              request_trace.clear_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE)
+              request_trace.clear_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH)
+
+              # Ensure tags are placed in rack.request span as desired
+              request_span.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE, last_script_name + last_route)
+              request_span.clear_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH)
+            end
+
             [status, headers, response]
 
           # rubocop:disable Lint/RescueException
@@ -142,10 +170,6 @@ def call(env)
           end
           # rubocop:enable Lint/RescueException
 
-          # rubocop:disable Metrics/AbcSize
-          # rubocop:disable Metrics/CyclomaticComplexity
-          # rubocop:disable Metrics/PerceivedComplexity
-          # rubocop:disable Metrics/MethodLength
           def set_request_tags!(trace, request_span, env, status, headers, response, original_env)
             request_header_collection = Header::RequestHeaderCollection.new(env)
 
diff --git a/lib/datadog/tracing/contrib/rails/patcher.rb b/lib/datadog/tracing/contrib/rails/patcher.rb
index d5837adf171..e2d147cd0cb 100644
--- a/lib/datadog/tracing/contrib/rails/patcher.rb
+++ b/lib/datadog/tracing/contrib/rails/patcher.rb
@@ -5,11 +5,24 @@
 require_relative 'middlewares'
 require_relative 'utils'
 require_relative '../semantic_logger/patcher'
+require_relative 'ext'
 
 module Datadog
   module Tracing
     module Contrib
       module Rails
+        # Patcher to trace rails routing done by JourneyRouter
+        module JourneyRouterPatch
+          def find_routes(*args)
+            result = super
+            integration_route = result.first[2].path.spec.to_s.gsub(/\(\.:format\)/, '') if result.any?
+            request_trace = Tracing.active_trace || TraceOperation.new
+            request_trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE, integration_route)
+            request_trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH, args.first.env['SCRIPT_NAME'])
+            result
+          end
+        end
+
         # Patcher enables patching of 'rails' module.
         module Patcher
           include Contrib::Patcher
@@ -41,6 +54,9 @@ def before_initialize(app)
               # Sometimes we don't want to activate middleware e.g. OpenTracing, etc.
               add_middleware(app) if Datadog.configuration.tracing[:rails][:middleware]
 
+              # ActionDispatch::Journey is not available or incompatible in Rails < 4.2.
+              ActionDispatch::Journey::Router.prepend(JourneyRouterPatch) if Integration.version >= Gem::Version.new('4.2')
+
               Rails::LogInjection.configure_log_tags(app.config)
             end
           end
diff --git a/lib/datadog/tracing/contrib/sinatra/tracer.rb b/lib/datadog/tracing/contrib/sinatra/tracer.rb
index 5b52e7649e7..e85f3ea6830 100644
--- a/lib/datadog/tracing/contrib/sinatra/tracer.rb
+++ b/lib/datadog/tracing/contrib/sinatra/tracer.rb
@@ -47,16 +47,16 @@ def route_eval
               configuration = Datadog.configuration.tracing[:sinatra]
               return super unless Tracing.enabled?
 
-              datadog_route = Sinatra::Env.route_path(env)
+              integration_route = Sinatra::Env.route_path(env)
 
               Tracing.trace(
                 Ext::SPAN_ROUTE,
                 service: configuration[:service_name],
                 span_type: Tracing::Metadata::Ext::HTTP::TYPE_INBOUND,
-                resource: "#{request.request_method} #{datadog_route}",
+                resource: "#{request.request_method} #{integration_route}",
               ) do |span, trace|
                 span.set_tag(Ext::TAG_APP_NAME, settings.name || settings.superclass.name)
-                span.set_tag(Ext::TAG_ROUTE_PATH, datadog_route)
+                span.set_tag(Ext::TAG_ROUTE_PATH, integration_route)
 
                 if request.script_name && !request.script_name.empty?
                   span.set_tag(Ext::TAG_SCRIPT_NAME, request.script_name)
@@ -73,6 +73,10 @@ def route_eval
 
                 Contrib::Analytics.set_measured(span)
 
+                _, path = env['sinatra.route'].split(' ', 2)
+                trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE, path)
+                trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH, env['SCRIPT_NAME'])
+                # binding.pry
                 super
               end
             end
diff --git a/lib/datadog/tracing/metadata/ext.rb b/lib/datadog/tracing/metadata/ext.rb
index e8d2a6f0ed2..a2c944bd1b9 100644
--- a/lib/datadog/tracing/metadata/ext.rb
+++ b/lib/datadog/tracing/metadata/ext.rb
@@ -86,6 +86,8 @@ module HTTP
           TYPE_TEMPLATE = 'template'
           TAG_CLIENT_IP = 'http.client_ip'
           HEADER_USER_AGENT = 'User-Agent'
+          TAG_ROUTE = 'http.route'
+          TAG_ROUTE_PATH = 'http.route.path'
 
           # General header functionality
           module Headers
diff --git a/sig/datadog/tracing/metadata/ext.rbs b/sig/datadog/tracing/metadata/ext.rbs
index aeca3b827a1..f5a236abffc 100644
--- a/sig/datadog/tracing/metadata/ext.rbs
+++ b/sig/datadog/tracing/metadata/ext.rbs
@@ -42,6 +42,8 @@ module Datadog
           ERROR_RANGE: ::Range[::Integer]
           TAG_BASE_URL: ::String
           TAG_METHOD: ::String
+          TAG_ROUTE: String
+          TAG_ROUTE_PATH: String
           TAG_STATUS_CODE: ::String
           TAG_USER_AGENT: ::String
           TAG_URL: ::String
diff --git a/spec/datadog/core/environment/execution_spec.rb b/spec/datadog/core/environment/execution_spec.rb
index 85bf70010e4..655a4a2a2ec 100644
--- a/spec/datadog/core/environment/execution_spec.rb
+++ b/spec/datadog/core/environment/execution_spec.rb
@@ -115,6 +115,7 @@ def test_it_does_something_useful
             gemfile(true) do
               source 'https://rubygems.org'
               gem 'spring', '>= 2.0.2'
+              gem 'concurrent-ruby', '#{Gem.loaded_specs['concurrent-ruby'].version}'
             end
 
             # Load the `bin/spring` file, just like a real Spring application would.
diff --git a/spec/datadog/tracing/contrib/http_route_spec.rb b/spec/datadog/tracing/contrib/http_route_spec.rb
new file mode 100644
index 00000000000..924db954d96
--- /dev/null
+++ b/spec/datadog/tracing/contrib/http_route_spec.rb
@@ -0,0 +1,332 @@
+require 'datadog/tracing/contrib/support/spec_helper'
+
+require 'grape'
+require 'rack/test'
+require 'sinatra'
+require 'rails'
+require 'action_controller'
+
+require 'ddtrace'
+
+RSpec.describe 'Multi-app testing for http.route' do
+  include Rack::Test::Methods
+
+  let(:options) { {} }
+
+  before do
+    Datadog.configure do |c|
+      c.tracing.instrument :sinatra, options
+      c.tracing.instrument :rack, options
+      c.tracing.instrument :grape, options
+      c.tracing.instrument :rails, options
+    end
+  end
+
+  after do
+    Datadog.registry[:sinatra].reset_configuration!
+    Datadog.registry[:rack].reset_configuration!
+    Datadog.registry[:grape].reset_configuration!
+    Datadog.registry[:rails].reset_configuration!
+  end
+
+  shared_context 'multi-app' do
+    let(:app) do
+      apps_to_build = apps
+
+      Rack::Builder.new do
+        apps_to_build.each do |route, app|
+          map route do
+            run app
+          end
+        end
+      end.to_app
+    end
+
+    let(:apps) do
+      {
+        '/' => rack_app,
+        '/rack' => rack_app,
+        '/sinatra' => sinatra_app,
+        '/grape' => grape_app,
+        '/rails' => rails_app,
+        '/rack/rack' => rack_app,
+        '/rack/sinatra' => sinatra_app,
+        '/rack/grape' => grape_app,
+        '/rack/rails' => rails_app
+      }
+    end
+
+    let(:rack_app) do
+      Rack::Builder.new do
+        map '/hello/world' do
+          run ->(_env) { [200, { 'content-type' => 'text/plain' }, 'hello world'] }
+        end
+      end
+    end
+
+    let(:sinatra_app) do
+      Class.new(Sinatra::Application) do
+        get '/hello/world' do
+          'hello world'
+        end
+
+        get '/hello/:id' do
+          "hello #{params[:id]}"
+        end
+      end
+    end
+
+    let(:grape_app) do
+      Class.new(Grape::API) do
+        get '/hello/world' do
+          'hello world'
+        end
+        get '/hello/:id' do
+          "hello #{params[:id]}"
+        end
+      end
+    end
+
+    let(:rails_app) do
+      Class.new(Rails::Engine) do
+        routes.draw do
+          get '/hello/world' => 'hello#world'
+          get '/hello/:id' => 'hello#show'
+        end
+      end
+    end
+
+    before do
+      stub_const(
+        'HelloController',
+        Class.new(ActionController::Base) do
+          def world
+            render plain: 'Hello, world!'
+          end
+
+          def show
+            render plain: "Hello, #{params[:id]}!"
+          end
+        end
+      )
+    end
+  end
+
+  context 'base routes' do
+    include_context 'multi-app'
+
+    describe 'request to base app' do
+      subject(:response) { get '/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to rack app' do
+      subject(:response) { get '/rack/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to sinatra app' do
+      subject(:response) { get '/sinatra/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/sinatra/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to sinatra app w/param' do
+      subject(:response) { get '/sinatra/hello/7' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/sinatra/hello/:id')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to grape app' do
+      subject(:response) { get '/grape/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/grape/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to grape app w/param' do
+      subject(:response) { get '/grape/hello/7' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/grape/hello/:id')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to rails app' do
+      subject(:response) { get '/rails/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rails/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to rails app w/param' do
+      subject(:response) { get '/rails/hello/7' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rails/hello/:id')
+
+          break
+        end
+      end
+    end
+  end
+
+  context 'nested rack routes' do
+    include_context 'multi-app'
+
+    describe 'request to nested sinatra app' do
+      subject(:response) { get '/rack/sinatra/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/sinatra/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to nested sinatra app w/param' do
+      subject(:response) { get '/rack/sinatra/hello/7' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/sinatra/hello/:id')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to nested grape app' do
+      subject(:response) { get '/rack/grape/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/grape/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to nested grape app w/param' do
+      subject(:response) { get '/rack/grape/hello/7' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/grape/hello/:id')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to nested rails app' do
+      subject(:response) { get '/rack/rails/hello/world' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/rails/hello/world')
+
+          break
+        end
+      end
+    end
+
+    describe 'request to nested rails app w/param' do
+      subject(:response) { get '/rack/rails/hello/7' }
+
+      it do
+        is_expected.to be_ok
+        spans.each do |span|
+          next unless span.name == Datadog::Tracing::Contrib::Rack::Ext::SPAN_REQUEST
+
+          expect(span.get_tag('http.route')).to eq('/rack/rails/hello/:id')
+
+          break
+        end
+      end
+    end
+  end
+end
diff --git a/spec/datadog/tracing/contrib/rails/rack_spec.rb b/spec/datadog/tracing/contrib/rails/rack_spec.rb
index 19c3b687e9f..79471b94326 100644
--- a/spec/datadog/tracing/contrib/rails/rack_spec.rb
+++ b/spec/datadog/tracing/contrib/rails/rack_spec.rb
@@ -144,6 +144,7 @@ def internal_server_error
       expect(request_span.service).to eq(tracer.default_service)
       expect(request_span.resource).to eq('TestController#full')
       expect(request_span.get_tag('http.url')).to eq('/full')
+      expect(request_span.get_tag('http.route')).to eq('/full') if Rails.version >= '4.2'
       expect(request_span.get_tag('http.method')).to eq('GET')
       expect(request_span.get_tag('http.status_code')).to eq('200')
       expect(request_span).to be_measured
@@ -379,6 +380,7 @@ def internal_server_error
       expect(request_span.span_type).to eq('web')
       expect(request_span.resource).to eq('TestController#error')
       expect(request_span.get_tag('http.url')).to eq('/error')
+      expect(request_span.get_tag('http.route')).to eq('/error') if Rails.version >= '4.2'
       expect(request_span.get_tag('http.method')).to eq('GET')
       expect(request_span.get_tag('http.status_code')).to eq('500')
       expect(request_span).to have_error
@@ -414,6 +416,7 @@ def internal_server_error
       expect(request_span.span_type).to eq('web')
       expect(request_span.resource).to eq('TestController#soft_error')
       expect(request_span.get_tag('http.url')).to eq('/soft_error')
+      expect(request_span.get_tag('http.route')).to eq('/soft_error') if Rails.version >= '4.2'
       expect(request_span.get_tag('http.method')).to eq('GET')
       expect(request_span.get_tag('http.status_code')).to eq('520')
       expect(request_span).to have_error
@@ -449,6 +452,7 @@ def internal_server_error
       expect(request_span.span_type).to eq('web')
       expect(request_span.resource).to eq('TestController#sub_error')
       expect(request_span.get_tag('http.url')).to eq('/sub_error')
+      expect(request_span.get_tag('http.route')).to eq('/sub_error') if Rails.version >= '4.2'
       expect(request_span.get_tag('http.method')).to eq('GET')
       expect(request_span.get_tag('http.status_code')).to eq('500')
       expect(request_span).to have_error