diff --git a/.editorconfig b/.editorconfig
new file mode 100644
index 0000000..eb57fc2
--- /dev/null
+++ b/.editorconfig
@@ -0,0 +1,14 @@
+root = true
+
+[*]
+end_of_line = lf
+insert_final_newline = true
+trim_trailing_whitespace = true
+
+[*.yml]
+indent_style = space
+indent_size = 2
+
+[*.md.erb]
+insert_final_newline = false
+trim_trailing_whitespace = false
diff --git a/.github/CODEOWNERS b/.github/CODEOWNERS
new file mode 100644
index 0000000..5a70a98
--- /dev/null
+++ b/.github/CODEOWNERS
@@ -0,0 +1 @@
+* @DataDog/lang-platform-ruby
diff --git a/.github/workflows/build-ruby.yml b/.github/workflows/build-ruby.yml
index 66831f6..de58bbc 100644
--- a/.github/workflows/build-ruby.yml
+++ b/.github/workflows/build-ruby.yml
@@ -86,7 +86,7 @@ jobs:
           docker run --platform linux/x86_64 --rm ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} ruby -e 'puts RUBY_DESCRIPTION'
           docker run --platform linux/x86_64 --rm ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} gem --version
           docker run --platform linux/x86_64 --rm ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} bundle --version
-          docker run --platform linux/x86_64 --rm -v "${PWD}":"${PWD}" -w "${PWD}" ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} /bin/sh -c 'bundle install && bundle exec rake test'
+          docker run --platform linux/x86_64 --rm -v "${PWD}":"${PWD}" -w "${PWD}" -e BUNDLE_GEMFILE=gemfiles/${{ matrix.engine }}-${{ matrix.version }}.gemfile ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} /bin/sh -c 'bundle install && bundle exec rake test'
 
       # Then, build image for aarch64 which, being emulated under qemu, is slower
       #
@@ -108,7 +108,7 @@ jobs:
           docker run --platform linux/aarch64 --rm ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} ruby -e 'puts RUBY_DESCRIPTION'
           docker run --platform linux/aarch64 --rm ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} gem --version
           docker run --platform linux/aarch64 --rm ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} bundle --version
-          docker run --platform linux/aarch64 --rm -v "${PWD}":"${PWD}" -w "${PWD}" ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} /bin/sh -c 'bundle install && bundle exec rake test'
+          docker run --platform linux/aarch64 --rm -v "${PWD}":"${PWD}" -w "${PWD}" -e BUNDLE_GEMFILE=gemfiles/${{ matrix.engine }}-${{ matrix.version }}.gemfile ${{ steps.vars.outputs.IMAGE }}:${{ steps.vars.outputs.TAG }} /bin/sh -c 'bundle install && bundle exec rake test'
 
       # Finally, assemble multi-arch image for a combined push to the registry
       #
diff --git a/.gitignore b/.gitignore
index 9bf08c3..106318a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -2,3 +2,4 @@
 /.direnv
 /vendor/bundle
 /Gemfile.lock
+/gemfiles/*.gemfile.lock
diff --git a/.rubocop.yml b/.rubocop.yml
new file mode 100644
index 0000000..1400412
--- /dev/null
+++ b/.rubocop.yml
@@ -0,0 +1,17 @@
+require:
+  - standard
+  - standard-custom
+  - standard-performance
+  - rubocop-performance
+  - rubocop-rake
+  - rubocop-minitest
+
+inherit_gem:
+  standard: config/base.yml
+  standard-custom: config/base.yml
+  standard-performance: config/base.yml
+
+AllCops:
+  TargetRubyVersion: 2.5
+  SuggestExtensions: false
+  NewCops: enable
diff --git a/.standard.yml b/.standard.yml
new file mode 100644
index 0000000..5852d57
--- /dev/null
+++ b/.standard.yml
@@ -0,0 +1,3 @@
+# For available configuration options, see:
+#   https://github.com/standardrb/standard
+ruby_version: 2.5
diff --git a/Gemfile b/Gemfile
index ba470b5..759fc9f 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,4 +1,4 @@
-source 'https://rubygems.org'
+# frozen_string_literal: true
 
-gem 'minitest'
-gem 'rake'
+gemfile = "#{RUBY_ENGINE}-#{RUBY_ENGINE_VERSION.split(".").take(2).join(".")}.gemfile"
+eval_gemfile "gemfiles/#{gemfile}"
diff --git a/gemfiles/jruby-9.2.gemfile b/gemfiles/jruby-9.2.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/jruby-9.2.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/jruby-9.3.gemfile b/gemfiles/jruby-9.3.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/jruby-9.3.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/jruby-9.4.gemfile b/gemfiles/jruby-9.4.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/jruby-9.4.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.1.gemfile b/gemfiles/ruby-2.1.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.1.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.2.gemfile b/gemfiles/ruby-2.2.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.2.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.3.gemfile b/gemfiles/ruby-2.3.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.3.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.4.gemfile b/gemfiles/ruby-2.4.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.4.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.5.gemfile b/gemfiles/ruby-2.5.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.5.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.6.gemfile b/gemfiles/ruby-2.6.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.6.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-2.7.gemfile b/gemfiles/ruby-2.7.gemfile
new file mode 100644
index 0000000..b3d4cd4
--- /dev/null
+++ b/gemfiles/ruby-2.7.gemfile
@@ -0,0 +1,7 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
diff --git a/gemfiles/ruby-3.0.gemfile b/gemfiles/ruby-3.0.gemfile
new file mode 100644
index 0000000..657d930
--- /dev/null
+++ b/gemfiles/ruby-3.0.gemfile
@@ -0,0 +1,18 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
+
+group :check do
+  gem "standard"
+  gem "rubocop"
+  gem "rubocop-rake"
+  gem "rubocop-minitest"
+end
+
+group :ide do
+  gem "ruby-lsp"
+end
diff --git a/gemfiles/ruby-3.1.gemfile b/gemfiles/ruby-3.1.gemfile
new file mode 100644
index 0000000..657d930
--- /dev/null
+++ b/gemfiles/ruby-3.1.gemfile
@@ -0,0 +1,18 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
+
+group :check do
+  gem "standard"
+  gem "rubocop"
+  gem "rubocop-rake"
+  gem "rubocop-minitest"
+end
+
+group :ide do
+  gem "ruby-lsp"
+end
diff --git a/gemfiles/ruby-3.2.gemfile b/gemfiles/ruby-3.2.gemfile
new file mode 100644
index 0000000..657d930
--- /dev/null
+++ b/gemfiles/ruby-3.2.gemfile
@@ -0,0 +1,18 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
+
+group :check do
+  gem "standard"
+  gem "rubocop"
+  gem "rubocop-rake"
+  gem "rubocop-minitest"
+end
+
+group :ide do
+  gem "ruby-lsp"
+end
diff --git a/gemfiles/ruby-3.3.gemfile b/gemfiles/ruby-3.3.gemfile
new file mode 100644
index 0000000..657d930
--- /dev/null
+++ b/gemfiles/ruby-3.3.gemfile
@@ -0,0 +1,18 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
+
+group :check do
+  gem "standard"
+  gem "rubocop"
+  gem "rubocop-rake"
+  gem "rubocop-minitest"
+end
+
+group :ide do
+  gem "ruby-lsp"
+end
diff --git a/gemfiles/ruby-3.4.gemfile b/gemfiles/ruby-3.4.gemfile
new file mode 100644
index 0000000..657d930
--- /dev/null
+++ b/gemfiles/ruby-3.4.gemfile
@@ -0,0 +1,18 @@
+source "https://rubygems.org"
+
+gem "rake"
+
+group :test do
+  gem "minitest"
+end
+
+group :check do
+  gem "standard"
+  gem "rubocop"
+  gem "rubocop-rake"
+  gem "rubocop-minitest"
+end
+
+group :ide do
+  gem "ruby-lsp"
+end