diff --git a/.rubocop_rspec_base.yml b/.rubocop_rspec_base.yml
index 4d0b7912a..3130e2676 100644
--- a/.rubocop_rspec_base.yml
+++ b/.rubocop_rspec_base.yml
@@ -1,4 +1,4 @@
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 # This file contains defaults for RSpec projects. Individual projects
diff --git a/.travis.yml b/.travis.yml
index 55be0958b..79f9f1eed 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -1,4 +1,4 @@
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 language: ruby
@@ -8,9 +8,7 @@ cache:
   directories:
     - ../bundle
 before_install:
-  # We need to ensure the latest version of Rubygems, unless we're on an old Ruby.
-  - gem update --system $(ruby -e "puts '2.7.8' if ENV['RUBY_VERSION'] >= '2.3.0'")
-  - gem install bundler
+  - "script/update_rubygems_and_install_bundler"
   - unset _JAVA_OPTIONS
   - "script/clone_all_rspec_repos"
 bundler_args: "--binstubs --standalone --without documentation --path ../bundle"
diff --git a/appveyor.yml b/appveyor.yml
index 3a32e7814..369422723 100644
--- a/appveyor.yml
+++ b/appveyor.yml
@@ -1,4 +1,4 @@
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 version: "{build}"
diff --git a/rspec-support.gemspec b/rspec-support.gemspec
index 50f3f8112..cf06bdcc1 100644
--- a/rspec-support.gemspec
+++ b/rspec-support.gemspec
@@ -35,7 +35,6 @@ Gem::Specification.new do |spec|
 
   spec.required_ruby_version = '>= 1.8.7'
 
-  spec.add_development_dependency "bundler",      "~> 1.3"
   spec.add_development_dependency "rake",         "~> 10.0.0"
   spec.add_development_dependency "thread_order", "~> 1.1.0"
 end
diff --git a/script/clone_all_rspec_repos b/script/clone_all_rspec_repos
index 419c2c18a..dcd4d914d 100755
--- a/script/clone_all_rspec_repos
+++ b/script/clone_all_rspec_repos
@@ -1,5 +1,5 @@
 #!/bin/bash
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 set -e
diff --git a/script/functions.sh b/script/functions.sh
index 6f552b473..1642bdb81 100644
--- a/script/functions.sh
+++ b/script/functions.sh
@@ -1,4 +1,4 @@
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
diff --git a/script/predicate_functions.sh b/script/predicate_functions.sh
index 2348b3716..cfdc471f7 100644
--- a/script/predicate_functions.sh
+++ b/script/predicate_functions.sh
@@ -1,4 +1,4 @@
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 function is_mri {
@@ -57,6 +57,14 @@ function is_mri_2plus {
   fi
 }
 
+function is_ruby_23_plus {
+  if ruby -e "exit(RUBY_VERSION.to_f >= 2.3)"; then
+    return 0
+  else
+    return 1
+  fi
+}
+
 function rspec_support_compatible {
   if [ "$MAINTENANCE_BRANCH" != "2-99-maintenance" ] && [ "$MAINTENANCE_BRANCH" != "2-14-maintenance" ]; then
     return 0
diff --git a/script/run_build b/script/run_build
index 293ba765f..891a05e96 100755
--- a/script/run_build
+++ b/script/run_build
@@ -1,5 +1,5 @@
 #!/bin/bash
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 set -e
diff --git a/script/travis_functions.sh b/script/travis_functions.sh
index 1bc5eccbf..8b89cc8bd 100644
--- a/script/travis_functions.sh
+++ b/script/travis_functions.sh
@@ -1,4 +1,4 @@
-# This file was generated on 2018-12-30T16:45:58+00:00 from the rspec-dev repo.
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
 # DO NOT modify it by hand as your changes will get lost the next time it is generated.
 
 # Taken from:
diff --git a/script/update_rubygems_and_install_bundler b/script/update_rubygems_and_install_bundler
new file mode 100755
index 000000000..bcf7e86db
--- /dev/null
+++ b/script/update_rubygems_and_install_bundler
@@ -0,0 +1,15 @@
+#!/bin/bash
+# This file was generated on 2019-01-03T20:34:23+00:00 from the rspec-dev repo.
+# DO NOT modify it by hand as your changes will get lost the next time it is generated.
+
+set -e
+source script/functions.sh
+
+if is_ruby_23_plus; then
+  gem update --system
+  gem install bundler
+else
+  echo "Warning installing older versions of Rubygems / Bundler"
+  gem update --system '2.7.8'
+  gem install bundler -v '1.17.3'
+fi