diff --git a/.gitlab-ci.yml b/.gitlab-ci.yml
index 72f8eeacbaf..65f6d927b37 100644
--- a/.gitlab-ci.yml
+++ b/.gitlab-ci.yml
@@ -108,6 +108,9 @@ build-gem:
   script:
     - export RUBY_PACKAGE_VERSION=$(cat tmp/version.txt)
     - export DATADOG_GEM_LOCATION=$(readlink -f pkg/datadog-*.gem)
+    - ruby -v
+    - gem -v
+    - bundler -v
     - ruby .gitlab/install_datadog_deps.rb
   artifacts:
     paths:
diff --git a/.gitlab/Dockerfile-2.7.8 b/.gitlab/Dockerfile-2.7.8
index 3d53736129f..447c2bfa2df 100644
--- a/.gitlab/Dockerfile-2.7.8
+++ b/.gitlab/Dockerfile-2.7.8
@@ -1,4 +1,5 @@
-# This is copied from official Docker image, but compile Ruby with `--disable-shared` instead.
+# This is copied from official Docker image
+# but compile Ruby with `--disable-shared` and update gem version
 
 FROM registry.ddbuild.io/images/mirror/buildpack-deps:buster
 
@@ -75,6 +76,8 @@ RUN set -eux; \
 # verify we have no "ruby" packages installed
 	if dpkg -l | grep -i ruby; then exit 1; fi; \
 	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# update gem version
+	gem update --system 3.3.27;\
 # rough smoke test
 	ruby --version; \
 	gem --version; \
diff --git a/.gitlab/Dockerfile-3.0.6 b/.gitlab/Dockerfile-3.0.6
index d33612bd083..08b2947d849 100644
--- a/.gitlab/Dockerfile-3.0.6
+++ b/.gitlab/Dockerfile-3.0.6
@@ -1,4 +1,5 @@
-# This is copied from official Docker image, but compile Ruby with `--disable-shared` instead.
+# This is copied from official Docker image
+# but compile Ruby with `--disable-shared` and update gem version
 
 FROM registry.ddbuild.io/images/mirror/buildpack-deps:buster
 
@@ -75,6 +76,8 @@ RUN set -eux; \
 # verify we have no "ruby" packages installed
 	if dpkg -l | grep -i ruby; then exit 1; fi; \
 	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# update gem version
+	gem update --system;\
 # rough smoke test
 	ruby --version; \
 	gem --version; \
diff --git a/.gitlab/Dockerfile-3.1.4 b/.gitlab/Dockerfile-3.1.4
index 867a1f4075e..c27d01a0081 100644
--- a/.gitlab/Dockerfile-3.1.4
+++ b/.gitlab/Dockerfile-3.1.4
@@ -1,4 +1,5 @@
-# This is copied from official Docker image, but compile Ruby with `--disable-shared` instead.
+# This is copied from official Docker image
+# but compile Ruby with `--disable-shared` and update gem version
 
 FROM registry.ddbuild.io/images/mirror/buildpack-deps:buster
 
@@ -75,6 +76,8 @@ RUN set -eux; \
 # verify we have no "ruby" packages installed
 	if dpkg -l | grep -i ruby; then exit 1; fi; \
 	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# update gem version
+	gem update --system;\
 # rough smoke test
 	ruby --version; \
 	gem --version; \
diff --git a/.gitlab/Dockerfile-3.2.2 b/.gitlab/Dockerfile-3.2.2
index 20348ab5e70..5f0b67f3a0a 100644
--- a/.gitlab/Dockerfile-3.2.2
+++ b/.gitlab/Dockerfile-3.2.2
@@ -1,4 +1,5 @@
-# This is copied from official Docker image, but compile Ruby with `--disable-shared` instead.
+# This is copied from official Docker image, but
+# compile Ruby with `--disable-shared` and update gem version
 
 FROM registry.ddbuild.io/images/mirror/buildpack-deps:buster
 
@@ -99,6 +100,8 @@ RUN set -eux; \
 # verify we have no "ruby" packages installed
 	if dpkg -l | grep -i ruby; then exit 1; fi; \
 	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# update gem version
+	gem update --system;\
 # rough smoke test
 	ruby --version; \
 	gem --version; \
diff --git a/.gitlab/install_datadog_deps.rb b/.gitlab/install_datadog_deps.rb
index 091bc35bc8b..f2c7f506fea 100755
--- a/.gitlab/install_datadog_deps.rb
+++ b/.gitlab/install_datadog_deps.rb
@@ -4,8 +4,22 @@
 require 'fileutils'
 require 'pathname'
 
+puts '=== RUBY_VERSION ==='
+puts RUBY_VERSION
+puts '=== RUBY_ENGINE ==='
+puts RUBY_ENGINE
+puts '=== RUBY_ENGINE_VERSION ==='
+puts RUBY_ENGINE_VERSION
+puts '=== RUBY_PLATFORM ==='
+puts RUBY_PLATFORM
+puts '=== GEM PLATFORM ==='
+puts Gem::Platform.local
+
 ruby_api_version = Gem.ruby_api_version
 
+puts '=== RUBY API VERISON ==='
+puts ruby_api_version
+
 current_path = Pathname.new(FileUtils.pwd)
 
 tmp_path = current_path.join('tmp')
@@ -19,6 +33,7 @@
 File.open(gemfile_file_path, 'w') do |file|
   file.write("source 'https://rubygems.org'\n")
   file.write("gem 'datadog', '#{ENV.fetch('RUBY_PACKAGE_VERSION')}', path: '#{current_path}'\n")
+  file.write("gem 'ffi', '1.16.3'\n")
   # Mimick outdated `msgpack` version, uncomment below line to test
   # file.write("gem 'msgpack', '1.6.0'\n")
 end
diff --git a/.vscode/settings.json b/.vscode/settings.json
new file mode 100644
index 00000000000..5e0380954a2
--- /dev/null
+++ b/.vscode/settings.json
@@ -0,0 +1,5 @@
+{
+  "files.associations": {
+    "Dockerfile*": "dockerfile"
+  }
+}
diff --git a/spec/datadog/release_gem_spec.rb b/spec/datadog/release_gem_spec.rb
index 51619fd2e7c..5d7769841b7 100644
--- a/spec/datadog/release_gem_spec.rb
+++ b/spec/datadog/release_gem_spec.rb
@@ -46,6 +46,7 @@
             |\.circleci
             |\.github
             |\.gitlab
+            |\.vscode
             |lib-injection
             |appraisal
             |benchmarks