diff --git a/.rubocop.yml b/.rubocop.yml
index 501c217172c..1ed0294bec8 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -443,4 +443,4 @@ Style/WordArray:
 
 # `!!` is the de facto way in Ruby to cast an Object to boolean.
 Style/DoubleNegation:
-  Enabled: false
\ No newline at end of file
+  Enabled: false
diff --git a/.rubocop_todo.yml b/.rubocop_todo.yml
index 90064a42cb0..07fef6aeb12 100644
--- a/.rubocop_todo.yml
+++ b/.rubocop_todo.yml
@@ -407,3 +407,7 @@ Style/FrozenStringLiteralComment:
 Metrics/BlockNesting:
   Exclude:
     - 'lib/datadog/appsec/configuration/settings.rb'
+
+Style/YodaCondition:
+  Exclude:
+    - 'spec/support/platform_helpers.rb'
diff --git a/Gemfile b/Gemfile
index cc56608b026..6f5671ebdf9 100644
--- a/Gemfile
+++ b/Gemfile
@@ -83,10 +83,12 @@ else
 end
 
 if RUBY_VERSION >= '2.6.0'
-  gem 'rubocop', '~> 1.34.0', require: false
+  # 1.50 is the last version to support Ruby 2.6
+  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', '~> 2.2', require: false
+  # 2.20 is the last version to support Ruby 2.6
+  gem 'rubocop-rspec', ['~> 2.20', '< 2.21'], require: false
 end
 
 # Optional extensions
diff --git a/lib/datadog/core/configuration/options.rb b/lib/datadog/core/configuration/options.rb
index 0e106d10166..8e1c8772cdc 100644
--- a/lib/datadog/core/configuration/options.rb
+++ b/lib/datadog/core/configuration/options.rb
@@ -101,7 +101,7 @@ def options_hash
           end
 
           def reset_options!
-            options.values.each(&:reset)
+            options.each_value(&:reset)
           end
 
           private
diff --git a/lib/datadog/core/configuration/settings.rb b/lib/datadog/core/configuration/settings.rb
index 748ede56418..c1f124b9ec5 100644
--- a/lib/datadog/core/configuration/settings.rb
+++ b/lib/datadog/core/configuration/settings.rb
@@ -99,6 +99,7 @@ def initialize(*_)
           # Datadog features are sending to the Agent or backend.
           # @default `DD_TRACE_DEBUG` environment variable, otherwise `false`
           # @return [Boolean]
+          # rubocop:disable Lint/RedundantRequireStatement
           option :debug do |o|
             o.env Datadog::Core::Configuration::Ext::Diagnostics::ENV_DEBUG_ENABLED
             o.default false
@@ -109,6 +110,7 @@ def initialize(*_)
               require 'pp' if enabled
             end
           end
+          # rubocop:enable Lint/RedundantRequireStatement
 
           # Internal {Datadog::Statsd} metrics collection.
           #
diff --git a/lib/datadog/profiling.rb b/lib/datadog/profiling.rb
index a16e857cea0..5266e42bb25 100644
--- a/lib/datadog/profiling.rb
+++ b/lib/datadog/profiling.rb
@@ -73,7 +73,7 @@ def self.enabled?
     end
 
     private_class_method def self.replace_noop_allocation_count
-      def self.allocation_count # rubocop:disable Lint/DuplicateMethods, Lint/NestedMethodDefinition (On purpose!)
+      def self.allocation_count # rubocop:disable Lint/NestedMethodDefinition (On purpose!)
         Datadog::Profiling::Collectors::CpuAndWallTimeWorker._native_allocation_count
       end
     end
diff --git a/lib/datadog/tracing/contrib/utils/quantization/http.rb b/lib/datadog/tracing/contrib/utils/quantization/http.rb
index 3e7d1196ee0..3e232421977 100644
--- a/lib/datadog/tracing/contrib/utils/quantization/http.rb
+++ b/lib/datadog/tracing/contrib/utils/quantization/http.rb
@@ -160,11 +160,11 @@ def obfuscate_query(query, options = {})
                  (?:"|%22)                                     # closing '"' at end of value
               )
              |(?: # other common secret values
-                 bearer(?:\s|%20)+[a-z0-9._\-]+
+                 bearer(?:\s|%20)+[a-z0-9._-]+
                 |token(?::|%3A)[a-z0-9]{13}
                 |gh[opsu]_[0-9a-zA-Z]{36}
                 |ey[I-L](?:[\w=-]|%3D)+\.ey[I-L](?:[\w=-]|%3D)+(?:\.(?:[\w.+/=-]|%3D|%2F|%2B)+)?
-                |-{5}BEGIN(?:[a-z\s]|%20)+PRIVATE(?:\s|%20)KEY-{5}[^\-]+-{5}END(?:[a-z\s]|%20)+PRIVATE(?:\s|%20)KEY(?:-{5})?(?:\n|%0A)?
+                |-{5}BEGIN(?:[a-z\s]|%20)+PRIVATE(?:\s|%20)KEY-{5}[^-]+-{5}END(?:[a-z\s]|%20)+PRIVATE(?:\s|%20)KEY(?:-{5})?(?:\n|%0A)?
                 |(?:ssh-(?:rsa|dss)|ecdsa-[a-z0-9]+-[a-z0-9]+)(?:\s|%20)*(?:[a-z0-9/.+]|%2F|%5C|%2B){100,}(?:=|%3D)*(?:(?:\s+)[a-z0-9._-]+)?
               )
             }ix.freeze
diff --git a/spec/datadog/appsec/remote_spec.rb b/spec/datadog/appsec/remote_spec.rb
index f1305bd64a4..bfc329d16ce 100644
--- a/spec/datadog/appsec/remote_spec.rb
+++ b/spec/datadog/appsec/remote_spec.rb
@@ -404,9 +404,7 @@
             context 'unsupported key' do
               let(:data) do
                 {
-                  'unsupported' => {
-
-                  }
+                  'unsupported' => {}
                 }
               end
 
@@ -452,9 +450,7 @@
             context 'without rules_data information' do
               let(:data) do
                 {
-                  'other_key' => {
-
-                  }
+                  'other_key' => {}
                 }
               end
 
diff --git a/spec/datadog/profiling/integration_spec.rb b/spec/datadog/profiling/integration_spec.rb
index 7494bbf2ce2..f9bdd67716f 100644
--- a/spec/datadog/profiling/integration_spec.rb
+++ b/spec/datadog/profiling/integration_spec.rb
@@ -255,9 +255,8 @@ def stack_frame_to_function_id(backtrace_location)
           is_expected.to have(4).items
 
           # All but last are unique
-          (0..-2).each do |i|
+          3.times do |i|
             stack_sample = stack_samples[i]
-
             expect(sample[i].to_h).to eq(
               location_id: stack_sample.frames.collect { |f| stack_frame_to_location_id(f) },
               value: [stack_sample.cpu_time_interval_ns, stack_sample.wall_time_interval_ns],
diff --git a/spec/datadog/tracing/contrib/aws/instrumentation_spec.rb b/spec/datadog/tracing/contrib/aws/instrumentation_spec.rb
index 5a0b8e9c1f9..e105ec66dc4 100644
--- a/spec/datadog/tracing/contrib/aws/instrumentation_spec.rb
+++ b/spec/datadog/tracing/contrib/aws/instrumentation_spec.rb
@@ -454,9 +454,7 @@
       end
 
       let(:responses) do
-        { create_topic: {
-
-        } }
+        { create_topic: {} }
       end
 
       it_behaves_like 'schema version span'
diff --git a/spec/datadog/tracing/contrib/rails/rails_active_job_spec.rb b/spec/datadog/tracing/contrib/rails/rails_active_job_spec.rb
index f08977c51b4..82af5bfbc93 100644
--- a/spec/datadog/tracing/contrib/rails/rails_active_job_spec.rb
+++ b/spec/datadog/tracing/contrib/rails/rails_active_job_spec.rb
@@ -77,7 +77,7 @@ def perform(test_retry: false, test_discard: false)
       expect(span.name).to eq('active_job.enqueue')
       expect(span.resource).to eq('ExampleJob')
       expect(span.get_tag('active_job.adapter')).to eq('ActiveJob::QueueAdapters::InlineAdapter')
-      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f\-]{32}/)
+      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f-]{32}/)
       expect(span.get_tag('active_job.job.queue')).to eq('mice')
       expect(span.get_tag(Datadog::Tracing::Metadata::Ext::TAG_COMPONENT))
         .to eq('active_job')
@@ -97,7 +97,7 @@ def perform(test_retry: false, test_discard: false)
       expect(span.name).to eq('active_job.enqueue')
       expect(span.resource).to eq('ExampleJob')
       expect(span.get_tag('active_job.adapter')).to eq('ActiveJob::QueueAdapters::InlineAdapter')
-      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f\-]{32}/)
+      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f-]{32}/)
       expect(span.get_tag('active_job.job.queue')).to eq('mice')
       expect(span.get_tag('active_job.job.scheduled_at').to_time).to be_within(1).of(scheduled_at)
       expect(span.get_tag(Datadog::Tracing::Metadata::Ext::TAG_COMPONENT))
@@ -117,7 +117,7 @@ def perform(test_retry: false, test_discard: false)
       expect(span.name).to eq('active_job.perform')
       expect(span.resource).to eq('ExampleJob')
       expect(span.get_tag('active_job.adapter')).to eq('ActiveJob::QueueAdapters::InlineAdapter')
-      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f\-]{32}/)
+      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f-]{32}/)
       expect(span.get_tag('active_job.job.queue')).to eq('elephants')
       expect(span.get_tag(Datadog::Tracing::Metadata::Ext::TAG_COMPONENT))
         .to eq('active_job')
@@ -140,7 +140,7 @@ def perform(test_retry: false, test_discard: false)
       expect(enqueue_retry_span.name).to eq('active_job.enqueue_retry')
       expect(enqueue_retry_span.resource).to eq('ExampleJob')
       expect(enqueue_retry_span.get_tag('active_job.adapter')).to eq('ActiveJob::QueueAdapters::InlineAdapter')
-      expect(enqueue_retry_span.get_tag('active_job.job.id')).to match(/[0-9a-f\-]{32}/)
+      expect(enqueue_retry_span.get_tag('active_job.job.id')).to match(/[0-9a-f-]{32}/)
       expect(enqueue_retry_span.get_tag('active_job.job.queue')).to eq('elephants')
       expect(enqueue_retry_span.get_tag('active_job.job.error')).to eq('JobRetryError')
       expect(enqueue_retry_span.get_tag(Datadog::Tracing::Metadata::Ext::TAG_COMPONENT))
@@ -159,7 +159,7 @@ def perform(test_retry: false, test_discard: false)
       expect(retry_stopped_span.name).to eq('active_job.retry_stopped')
       expect(retry_stopped_span.resource).to eq('ExampleJob')
       expect(retry_stopped_span.get_tag('active_job.adapter')).to eq('ActiveJob::QueueAdapters::InlineAdapter')
-      expect(retry_stopped_span.get_tag('active_job.job.id')).to match(/[0-9a-f\-]{32}/)
+      expect(retry_stopped_span.get_tag('active_job.job.id')).to match(/[0-9a-f-]{32}/)
       expect(retry_stopped_span.get_tag('active_job.job.queue')).to eq('elephants')
       expect(retry_stopped_span.get_tag('active_job.job.error')).to eq('JobRetryError')
       expect(retry_stopped_span.get_tag(Datadog::Tracing::Metadata::Ext::TAG_COMPONENT))
@@ -183,7 +183,7 @@ def perform(test_retry: false, test_discard: false)
       expect(span.name).to eq('active_job.discard')
       expect(span.resource).to eq('ExampleJob')
       expect(span.get_tag('active_job.adapter')).to eq('ActiveJob::QueueAdapters::InlineAdapter')
-      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f\-]{32}/)
+      expect(span.get_tag('active_job.job.id')).to match(/[0-9a-f-]{32}/)
       expect(span.get_tag('active_job.job.queue')).to eq('elephants')
       expect(span.get_tag('active_job.job.error')).to eq('JobDiscardError')
       expect(span.get_tag(Datadog::Tracing::Metadata::Ext::TAG_COMPONENT))
diff --git a/spec/support/platform_helpers.rb b/spec/support/platform_helpers.rb
index 0c664fbdb28..590a332cbd9 100644
--- a/spec/support/platform_helpers.rb
+++ b/spec/support/platform_helpers.rb
@@ -1,3 +1,5 @@
+# frozen_string_literal: true
+
 require 'os'
 
 module PlatformHelpers
@@ -6,15 +8,15 @@ module PlatformHelpers
   # Ruby runtime engines
 
   def mri?
-    RUBY_ENGINE == 'ruby'.freeze
+    RUBY_ENGINE == 'ruby'
   end
 
   def jruby?
-    RUBY_ENGINE == 'jruby'.freeze
+    RUBY_ENGINE == 'jruby'
   end
 
   def truffleruby?
-    RUBY_ENGINE == 'truffleruby'.freeze
+    RUBY_ENGINE == 'truffleruby'
   end
 
   def engine_version