diff --git a/bin/console b/bin/console
deleted file mode 100755
index f29b0521..00000000
--- a/bin/console
+++ /dev/null
@@ -1,15 +0,0 @@
-#!/usr/bin/env ruby
-# frozen_string_literal: true
-
-require "bundler/setup"
-require "datadog/ci"
-
-# You can add fixtures and/or initialization code here to make experimenting
-# with your gem easier. You can also use a different console, if you like.
-
-# (If you use this, don't forget to add pry to your Gemfile!)
-# require "pry"
-# Pry.start
-
-require "irb"
-IRB.start(__FILE__)
diff --git a/bin/ddcirb b/bin/ddcirb
new file mode 100755
index 00000000..b2eab361
--- /dev/null
+++ b/bin/ddcirb
@@ -0,0 +1,11 @@
+#!/usr/bin/env ruby
+
+rubyopts = [
+  "-rdatadog/ci/auto_instrument"
+]
+
+existing_rubyopt = ENV["RUBYOPT"]
+
+ENV["RUBYOPT"] = existing_rubyopt ? "#{existing_rubyopt} #{rubyopts.join(" ")}" : rubyopts.join(" ")
+
+::Kernel.exec(*ARGV)
diff --git a/bin/setup b/bin/setup
deleted file mode 100755
index dce67d86..00000000
--- a/bin/setup
+++ /dev/null
@@ -1,8 +0,0 @@
-#!/usr/bin/env bash
-set -euo pipefail
-IFS=$'\n\t'
-set -vx
-
-bundle install
-
-# Do any other automated setup that you need to do here
diff --git a/datadog-ci.gemspec b/datadog-ci.gemspec
index bdaa2d95..71712c51 100644
--- a/datadog-ci.gemspec
+++ b/datadog-ci.gemspec
@@ -22,6 +22,7 @@ Gem::Specification.new do |spec|
 
   spec.homepage = "https://github.com/DataDog/datadog-ci-rb"
   spec.license = "BSD-3-Clause"
+  spec.executables = ["ddcirb"]
 
   spec.metadata["allowed_push_host"] = "https://rubygems.org"
   spec.metadata["changelog_uri"] = "https://github.com/DataDog/datadog-ci-rb/blob/main/CHANGELOG.md"
@@ -36,6 +37,7 @@ Gem::Specification.new do |spec|
       README.md
       ext/**/*
       lib/**/*
+      bin/**/*
     ]].select { |fn| File.file?(fn) } # We don't want directories, only files
       .reject { |fn| fn.end_with?(".so", ".bundle") } # Exclude local native binary artifacts
 
diff --git a/lib/datadog/ci.rb b/lib/datadog/ci.rb
index a5efc9f8..60152014 100644
--- a/lib/datadog/ci.rb
+++ b/lib/datadog/ci.rb
@@ -6,6 +6,7 @@
 require_relative "ci/ext/app_types"
 require_relative "ci/ext/telemetry"
 
+require "datadog"
 require "datadog/core"
 
 module Datadog
diff --git a/lib/datadog/ci/auto_instrument.rb b/lib/datadog/ci/auto_instrument.rb
new file mode 100644
index 00000000..da0b0148
--- /dev/null
+++ b/lib/datadog/ci/auto_instrument.rb
@@ -0,0 +1,4 @@
+require "datadog/ci"
+require "datadog/ci/contrib/contrib"
+
+Datadog::CI::Contrib.auto_instrument!
diff --git a/lib/datadog/ci/contrib/contrib.rb b/lib/datadog/ci/contrib/contrib.rb
index 457a7e74..19378453 100644
--- a/lib/datadog/ci/contrib/contrib.rb
+++ b/lib/datadog/ci/contrib/contrib.rb
@@ -5,18 +5,83 @@
 module Datadog
   module CI
     module Contrib
+      @@auto_instrumented_integrations = {}
+
+      def self.auto_instrument!
+        Datadog.logger.debug("Auto instrumenting all integrations...")
+
+        Integration.registry.each do |name, integration|
+          next unless integration.auto_instrument?
+
+          Datadog.logger.debug "#{name} is allowed to be auto instrumented"
+
+          if integration.class.loaded?
+            Datadog.logger.debug("#{name} is already loaded")
+
+            configure_ci_with_framework(name)
+          else
+            Datadog.logger.debug("#{name} is not loaded yet")
+
+            Datadog.logger.debug("Registering on require hook for #{name}...")
+
+            @@auto_instrumented_integrations[name] = integration
+          end
+        end
+
+        enable_trace_requires
+      end
+
+      def self.enable_trace_requires
+        @@trp = TracePoint.new(:script_compiled) do |tp|
+          on_require(tp.instruction_sequence.path)
+        end
+
+        @@trp.enable
+      end
+
+      def self.disable_trace_requires
+        @@trp.disable
+      end
+
+      def self.on_require(path)
+        Datadog.logger.debug { "Path: #{path}" }
+        @@auto_instrumented_integrations.each do |gem_name, integration|
+          if path.include?(gem_name.to_s) && integration.class.loaded?
+            Datadog.logger.debug { "Gem '#{gem_name}' loaded. Configuring integration." }
+
+            Contrib.disable_trace_requires
+
+            configure_ci_with_framework(gem_name)
+          end
+        end
+      rescue => e
+        Datadog.logger.debug do
+          "Failed to execute callback for gem: #{e.class.name} #{e.message} at #{Array(e.backtrace).join("\n")}"
+        end
+      end
+
+      def self.configure_ci_with_framework(framework)
+        Datadog.logger.debug("Configuring CI with #{framework}...")
+
+        Datadog.configure do |c|
+          c.tracing.enabled = true
+          c.ci.enabled = true
+          c.ci.instrument framework
+        end
+      end
+
       # This method auto instruments all test libraries (ex: selenium-webdriver).
       # It is intended to be called when test session starts to add additional capabilities to test visibility.
       #
       # This method does not automatically instrument test frameworks (ex: RSpec, Cucumber, etc), it requires
       # test framework to be already instrumented.
-      def self.auto_instrument_on_session_start!
-        Datadog.logger.debug("Auto instrumenting all integrations...")
+      def self.instrument_on_session_start!
+        Datadog.logger.debug("Instrumenting additional libraries when session starts...")
 
         Integration.registry.each do |name, integration|
-          next unless integration.auto_instrument?
+          next unless integration.instrument_on_session_start?
 
-          Datadog.logger.debug "#{name} is allowed to be auto instrumented"
+          Datadog.logger.debug "#{name} is allowed to be instrumented when session starts"
 
           patch_results = integration.patch
           if patch_results == true
diff --git a/lib/datadog/ci/contrib/cucumber/integration.rb b/lib/datadog/ci/contrib/cucumber/integration.rb
index bbbcf82c..c11542e2 100644
--- a/lib/datadog/ci/contrib/cucumber/integration.rb
+++ b/lib/datadog/ci/contrib/cucumber/integration.rb
@@ -21,15 +21,18 @@ def self.version
           end
 
           def self.loaded?
-            !defined?(::Cucumber).nil? && !defined?(::Cucumber::Runtime).nil?
+            !defined?(::Cucumber).nil? && !defined?(::Cucumber::Runtime).nil? && !defined?(::Cucumber::Configuration).nil?
           end
 
           def self.compatible?
             super && version >= MINIMUM_VERSION
           end
 
-          # test environments should not auto instrument test libraries
           def auto_instrument?
+            true
+          end
+
+          def instrument_on_session_start?
             false
           end
 
diff --git a/lib/datadog/ci/contrib/minitest/integration.rb b/lib/datadog/ci/contrib/minitest/integration.rb
index ce1cd89c..fb83b52c 100644
--- a/lib/datadog/ci/contrib/minitest/integration.rb
+++ b/lib/datadog/ci/contrib/minitest/integration.rb
@@ -21,15 +21,19 @@ def self.version
           end
 
           def self.loaded?
-            !defined?(::Minitest).nil?
+            !defined?(::Minitest).nil? && !defined?(::Minitest::Runnable).nil? && !defined?(::Minitest::Test).nil? &&
+              !defined?(::Minitest::CompositeReporter).nil?
           end
 
           def self.compatible?
             super && version >= MINIMUM_VERSION
           end
 
-          # test environments should not auto instrument test libraries
           def auto_instrument?
+            true
+          end
+
+          def instrument_on_session_start?
             false
           end
 
diff --git a/lib/datadog/ci/contrib/rspec/integration.rb b/lib/datadog/ci/contrib/rspec/integration.rb
index c0279c79..94d9aff4 100644
--- a/lib/datadog/ci/contrib/rspec/integration.rb
+++ b/lib/datadog/ci/contrib/rspec/integration.rb
@@ -22,15 +22,22 @@ def self.version
 
           def self.loaded?
             !defined?(::RSpec).nil? && !defined?(::RSpec::Core).nil? &&
-              !defined?(::RSpec::Core::Example).nil?
+              !defined?(::RSpec::Core::Example).nil? &&
+              !defined?(::RSpec::Core::Runner).nil? &&
+              !defined?(::RSpec::Core::ExampleGroup).nil?
           end
 
           def self.compatible?
             super && version >= MINIMUM_VERSION
           end
 
-          # test environments should not auto instrument test libraries
+          # TODO: rename the following 2 methods: the difference is not about auto or on session start:
+          # the difference is that the first one is for test frameworks, the second one is for additional libraries
           def auto_instrument?
+            true
+          end
+
+          def instrument_on_session_start?
             false
           end
 
diff --git a/lib/datadog/ci/contrib/selenium/integration.rb b/lib/datadog/ci/contrib/selenium/integration.rb
index 6d3e9bec..57713aad 100644
--- a/lib/datadog/ci/contrib/selenium/integration.rb
+++ b/lib/datadog/ci/contrib/selenium/integration.rb
@@ -29,8 +29,12 @@ def self.compatible?
             super && version >= MINIMUM_VERSION
           end
 
-          # additional instrumentations for test helpers are auto instrumented on test session start
           def auto_instrument?
+            false
+          end
+
+          # additional instrumentations for test helpers are instrumented on test session start
+          def instrument_on_session_start?
             true
           end
 
diff --git a/lib/datadog/ci/test_visibility/component.rb b/lib/datadog/ci/test_visibility/component.rb
index 572ce78b..2a5b5380 100644
--- a/lib/datadog/ci/test_visibility/component.rb
+++ b/lib/datadog/ci/test_visibility/component.rb
@@ -146,7 +146,7 @@ def on_test_session_started(test_session)
           git_tree_upload_worker.perform(test_session.git_repository_url)
 
           # finds and instruments additional test libraries that we support (ex: selenium-webdriver)
-          Contrib.auto_instrument_on_session_start!
+          Contrib.instrument_on_session_start!
 
           # sends internal telemetry events
           Telemetry.test_session_started(test_session)
diff --git a/sig/datadog/ci/contrib/selenium/integration.rbs b/sig/datadog/ci/contrib/selenium/integration.rbs
index 15a9b87a..9c04ea59 100644
--- a/sig/datadog/ci/contrib/selenium/integration.rbs
+++ b/sig/datadog/ci/contrib/selenium/integration.rbs
@@ -14,7 +14,7 @@ module Datadog
 
           def self.compatible?: () -> bool
 
-          def auto_instrument?: () -> true
+          def auto_instrument?: () -> bool
 
           def new_configuration: () -> untyped
 
diff --git a/spec/datadog/ci/configuration/settings_spec.rb b/spec/datadog/ci/configuration/settings_spec.rb
index b70eae46..2ee655ee 100644
--- a/spec/datadog/ci/configuration/settings_spec.rb
+++ b/spec/datadog/ci/configuration/settings_spec.rb
@@ -38,6 +38,10 @@ def self.auto_instrument?
     false
   end
 
+  def instrument_on_session_start?
+    false
+  end
+
   def patcher
     Patcher
   end
diff --git a/spec/datadog/ci/contrib/cucumber/integration_spec.rb b/spec/datadog/ci/contrib/cucumber/integration_spec.rb
index de70ee02..32cc415e 100644
--- a/spec/datadog/ci/contrib/cucumber/integration_spec.rb
+++ b/spec/datadog/ci/contrib/cucumber/integration_spec.rb
@@ -57,7 +57,7 @@
   describe "#auto_instrument?" do
     subject(:auto_instrument?) { integration.auto_instrument? }
 
-    it { is_expected.to be(false) }
+    it { is_expected.to be(true) }
   end
 
   describe "#configuration" do
diff --git a/spec/datadog/ci/contrib/minitest/integration_spec.rb b/spec/datadog/ci/contrib/minitest/integration_spec.rb
index 105f17da..5663b486 100644
--- a/spec/datadog/ci/contrib/minitest/integration_spec.rb
+++ b/spec/datadog/ci/contrib/minitest/integration_spec.rb
@@ -49,7 +49,7 @@
   describe "#auto_instrument?" do
     subject(:auto_instrument?) { integration.auto_instrument? }
 
-    it { is_expected.to be(false) }
+    it { is_expected.to be(true) }
   end
 
   describe "#configuration" do
diff --git a/spec/datadog/ci/contrib/rspec/integration_spec.rb b/spec/datadog/ci/contrib/rspec/integration_spec.rb
index b387a13a..9ea21ea3 100644
--- a/spec/datadog/ci/contrib/rspec/integration_spec.rb
+++ b/spec/datadog/ci/contrib/rspec/integration_spec.rb
@@ -49,7 +49,7 @@
   describe "#auto_instrument?" do
     subject(:auto_instrument?) { integration.auto_instrument? }
 
-    it { is_expected.to be(false) }
+    it { is_expected.to be(true) }
   end
 
   describe "#configuration" do
diff --git a/spec/datadog/ci/release_gem_spec.rb b/spec/datadog/ci/release_gem_spec.rb
index 5708c587..8567fbe6 100644
--- a/spec/datadog/ci/release_gem_spec.rb
+++ b/spec/datadog/ci/release_gem_spec.rb
@@ -40,7 +40,6 @@
             |\.circleci
             |\.github
             |\.vscode
-            | bin
             |gemfiles
             |integration
             |tasks