diff --git a/Steepfile b/Steepfile
index adcd6d99..6571d23e 100644
--- a/Steepfile
+++ b/Steepfile
@@ -15,6 +15,7 @@ target :lib do
   library "securerandom"
   library "tmpdir"
   library "fileutils"
+  library "socket"
 
   repo_path "vendor/rbs"
   library "ddtrace"
diff --git a/lib/datadog/ci/configuration/components.rb b/lib/datadog/ci/configuration/components.rb
index 4c8414f3..329f9546 100644
--- a/lib/datadog/ci/configuration/components.rb
+++ b/lib/datadog/ci/configuration/components.rb
@@ -96,6 +96,8 @@ def activate_ci!(settings)
           )
 
           itr = ITR::Runner.new(
+            api: test_visibility_api,
+            dd_env: settings.env,
             coverage_writer: coverage_writer,
             enabled: settings.ci.enabled && settings.ci.itr_enabled
           )
diff --git a/lib/datadog/ci/ext/test.rb b/lib/datadog/ci/ext/test.rb
index 7c548203..0d219b96 100644
--- a/lib/datadog/ci/ext/test.rb
+++ b/lib/datadog/ci/ext/test.rb
@@ -43,6 +43,7 @@ module Test
         # Environment runtime tags
         TAG_OS_ARCHITECTURE = "os.architecture"
         TAG_OS_PLATFORM = "os.platform"
+        TAG_OS_VERSION = "os.version"
         TAG_RUNTIME_NAME = "runtime.name"
         TAG_RUNTIME_VERSION = "runtime.version"
 
diff --git a/lib/datadog/ci/itr/runner.rb b/lib/datadog/ci/itr/runner.rb
index 85d23bf6..44d72877 100644
--- a/lib/datadog/ci/itr/runner.rb
+++ b/lib/datadog/ci/itr/runner.rb
@@ -10,6 +10,7 @@
 require_relative "../utils/parsing"
 
 require_relative "coverage/event"
+require_relative "skippable"
 
 module Datadog
   module CI
@@ -18,20 +19,30 @@ module ITR
       # Integrates with backend to provide test impact analysis data and
       # skip tests that are not impacted by the changes
       class Runner
+        attr_reader :correlation_id, :skippable_tests
+
         def initialize(
+          dd_env:,
+          api: nil,
           coverage_writer: nil,
           enabled: false
         )
           @enabled = enabled
+          @api = api
+          @dd_env = dd_env
+
           @test_skipping_enabled = false
           @code_coverage_enabled = false
 
           @coverage_writer = coverage_writer
 
+          @correlation_id = nil
+          @skippable_tests = []
+
           Datadog.logger.debug("ITR Runner initialized with enabled: #{@enabled}")
         end
 
-        def configure(remote_configuration, test_session)
+        def configure(remote_configuration, test_session:, git_tree_upload_worker:)
           Datadog.logger.debug("Configuring ITR Runner with remote configuration: #{remote_configuration}")
 
           @enabled = Utils::Parsing.convert_to_bool(
@@ -55,6 +66,8 @@ def configure(remote_configuration, test_session)
           load_datadog_cov! if @code_coverage_enabled
 
           Datadog.logger.debug("Configured ITR Runner with enabled: #{@enabled}, skipping_tests: #{@test_skipping_enabled}, code_coverage: #{@code_coverage_enabled}")
+
+          fetch_skippable_tests(test_session: test_session, git_tree_upload_worker: git_tree_upload_worker)
         end
 
         def enabled?
@@ -129,6 +142,20 @@ def ensure_test_source_covered(test_source_file, coverage)
 
           coverage[absolute_test_source_file_path] = true
         end
+
+        def fetch_skippable_tests(test_session:, git_tree_upload_worker:)
+          return unless skipping_tests?
+
+          # we can only request skippable tests if git metadata is already uploaded
+          git_tree_upload_worker.wait_until_done
+
+          skippable_response = Skippable.new(api: @api, dd_env: @dd_env).fetch_skippable_tests(test_session)
+          @correlation_id = skippable_response.correlation_id
+          @skippable_tests = skippable_response.tests
+
+          Datadog.logger.debug { "Fetched skippable tests: \n #{@skippable_tests}" }
+          Datadog.logger.debug { "ITR correlation ID: #{@correlation_id}" }
+        end
       end
     end
   end
diff --git a/lib/datadog/ci/itr/skippable.rb b/lib/datadog/ci/itr/skippable.rb
index 0c155227..28b3c1b6 100644
--- a/lib/datadog/ci/itr/skippable.rb
+++ b/lib/datadog/ci/itr/skippable.rb
@@ -4,24 +4,12 @@
 
 require_relative "../ext/transport"
 require_relative "../ext/test"
+require_relative "../utils/test_run"
 
 module Datadog
   module CI
     module ITR
       class Skippable
-        class Test
-          attr_reader :name, :suite
-
-          def initialize(name:, suite:)
-            @name = name
-            @suite = suite
-          end
-
-          def ==(other)
-            name == other.name && suite == other.suite
-          end
-        end
-
         class Response
           def initialize(http_response)
             @http_response = http_response
@@ -38,13 +26,17 @@ def correlation_id
           end
 
           def tests
+            res = Set.new
+
             payload.fetch("data", [])
-              .filter_map do |test_data|
+              .each do |test_data|
                 next unless test_data["type"] == Ext::Test::ITR_TEST_SKIPPING_MODE
 
                 attrs = test_data["attributes"] || {}
-                Test.new(name: attrs["name"], suite: attrs["suite"])
+                res << Utils::TestRun.test_full_name(attrs["name"], attrs["suite"])
               end
+
+            res
           end
 
           private
@@ -65,7 +57,7 @@ def payload
           end
         end
 
-        def initialize(api: nil, dd_env: nil)
+        def initialize(dd_env:, api: nil)
           @api = api
           @dd_env = dd_env
         end
@@ -98,10 +90,11 @@ def payload(test_session)
                 "repository_url" => test_session.git_repository_url,
                 "sha" => test_session.git_commit_sha,
                 "configurations" => {
-                  "os.platform" => test_session.os_platform,
-                  "os.architecture" => test_session.os_architecture,
-                  "runtime.name" => test_session.runtime_name,
-                  "runtime.version" => test_session.runtime_version
+                  Ext::Test::TAG_OS_PLATFORM => test_session.os_platform,
+                  Ext::Test::TAG_OS_ARCHITECTURE => test_session.os_architecture,
+                  Ext::Test::TAG_OS_VERSION => test_session.os_version,
+                  Ext::Test::TAG_RUNTIME_NAME => test_session.runtime_name,
+                  Ext::Test::TAG_RUNTIME_VERSION => test_session.runtime_version
                 }
               }
             }
diff --git a/lib/datadog/ci/span.rb b/lib/datadog/ci/span.rb
index 481c87e1..097fc710 100644
--- a/lib/datadog/ci/span.rb
+++ b/lib/datadog/ci/span.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require "datadog/core/environment/platform"
+
 require_relative "ext/test"
 require_relative "utils/test_run"
 
@@ -151,6 +153,12 @@ def os_platform
         tracer_span.get_tag(Ext::Test::TAG_OS_PLATFORM)
       end
 
+      # Returns the OS version extracted from the environment.
+      # @return [String] OS version.
+      def os_version
+        tracer_span.get_tag(Ext::Test::TAG_OS_VERSION)
+      end
+
       # Returns the runtime name extracted from the environment.
       # @return [String] runtime name.
       def runtime_name
@@ -166,6 +174,7 @@ def runtime_version
       def set_environment_runtime_tags
         tracer_span.set_tag(Ext::Test::TAG_OS_ARCHITECTURE, ::RbConfig::CONFIG["host_cpu"])
         tracer_span.set_tag(Ext::Test::TAG_OS_PLATFORM, ::RbConfig::CONFIG["host_os"])
+        tracer_span.set_tag(Ext::Test::TAG_OS_VERSION, Core::Environment::Platform.kernel_release)
         tracer_span.set_tag(Ext::Test::TAG_RUNTIME_NAME, Core::Environment::Ext::LANG_ENGINE)
         tracer_span.set_tag(Ext::Test::TAG_RUNTIME_VERSION, Core::Environment::Ext::ENGINE_VERSION)
         tracer_span.set_tag(Ext::Test::TAG_COMMAND, Utils::TestRun.command)
diff --git a/lib/datadog/ci/test_visibility/recorder.rb b/lib/datadog/ci/test_visibility/recorder.rb
index 83b92e44..d3a07414 100644
--- a/lib/datadog/ci/test_visibility/recorder.rb
+++ b/lib/datadog/ci/test_visibility/recorder.rb
@@ -229,7 +229,12 @@ def configure_library(test_session)
               Datadog.logger.debug { "git metadata upload did not complete in time when configuring library" }
             end
           end
-          @itr.configure(remote_configuration.payload, test_session)
+
+          @itr.configure(
+            remote_configuration.payload,
+            test_session: test_session,
+            git_tree_upload_worker: @git_tree_upload_worker
+          )
         end
 
         def skip_tracing(block = nil)
diff --git a/lib/datadog/ci/test_visibility/transport.rb b/lib/datadog/ci/test_visibility/transport.rb
index 572de392..4116d513 100644
--- a/lib/datadog/ci/test_visibility/transport.rb
+++ b/lib/datadog/ci/test_visibility/transport.rb
@@ -14,7 +14,7 @@ class Transport < Datadog::CI::Transport::EventPlatformTransport
 
         def initialize(
           api:,
-          dd_env: nil,
+          dd_env:,
           serializers_factory: Datadog::CI::TestVisibility::Serializers::Factories::TestLevel,
           max_payload_size: DEFAULT_MAX_PAYLOAD_SIZE
         )
diff --git a/lib/datadog/ci/transport/http.rb b/lib/datadog/ci/transport/http.rb
index a8ece315..a00ff3bf 100644
--- a/lib/datadog/ci/transport/http.rb
+++ b/lib/datadog/ci/transport/http.rb
@@ -4,6 +4,7 @@
 require "datadog/core/transport/http/adapters/net"
 require "datadog/core/transport/http/env"
 require "datadog/core/transport/request"
+require "socket"
 
 require_relative "gzip"
 require_relative "../ext/transport"
@@ -20,6 +21,8 @@ class HTTP
           :compress
 
         DEFAULT_TIMEOUT = 30
+        MAX_RETRIES = 3
+        INITIAL_BACKOFF = 1
 
         def initialize(host:, timeout: DEFAULT_TIMEOUT, port: nil, ssl: true, compress: false)
           @host = host
@@ -29,7 +32,7 @@ def initialize(host:, timeout: DEFAULT_TIMEOUT, port: nil, ssl: true, compress:
           @compress = compress.nil? ? false : compress
         end
 
-        def request(path:, payload:, headers:, verb: "post")
+        def request(path:, payload:, headers:, verb: "post", retries: MAX_RETRIES, backoff: INITIAL_BACKOFF)
           if compress
             headers[Ext::Transport::HEADER_CONTENT_ENCODING] = Ext::Transport::CONTENT_ENCODING_GZIP
             payload = Gzip.compress(payload)
@@ -41,9 +44,7 @@ def request(path:, payload:, headers:, verb: "post")
           end
 
           response = ResponseDecorator.new(
-            adapter.call(
-              build_env(path: path, payload: payload, headers: headers, verb: verb)
-            )
+            perform_http_call(path: path, payload: payload, headers: headers, verb: verb, retries: retries, backoff: backoff)
           )
 
           Datadog.logger.debug do
@@ -55,6 +56,25 @@ def request(path:, payload:, headers:, verb: "post")
 
         private
 
+        def perform_http_call(path:, payload:, headers:, verb:, retries: MAX_RETRIES, backoff: INITIAL_BACKOFF)
+          adapter.call(
+            build_env(path: path, payload: payload, headers: headers, verb: verb)
+          )
+        rescue Timeout::Error, Errno::EINVAL, Errno::ECONNRESET, EOFError, SocketError, Net::HTTPBadResponse => e
+          Datadog.logger.debug("Failed to send request with #{e} (#{e.message})")
+
+          if retries.positive?
+            sleep(backoff)
+
+            perform_http_call(
+              path: path, payload: payload, headers: headers, verb: verb, retries: retries - 1, backoff: backoff * 2
+            )
+          else
+            Datadog.logger.error("Failed to send request after #{MAX_RETRIES} retries")
+            raise e
+          end
+        end
+
         def build_env(path:, payload:, headers:, verb:)
           env = Datadog::Core::Transport::HTTP::Env.new(
             Datadog::Core::Transport::Request.new
diff --git a/lib/datadog/ci/transport/remote_settings_api.rb b/lib/datadog/ci/transport/remote_settings_api.rb
index ec252bd0..03ac76a1 100644
--- a/lib/datadog/ci/transport/remote_settings_api.rb
+++ b/lib/datadog/ci/transport/remote_settings_api.rb
@@ -51,7 +51,7 @@ def default_payload
           end
         end
 
-        def initialize(api: nil, dd_env: nil)
+        def initialize(dd_env:, api: nil)
           @api = api
           @dd_env = dd_env
         end
@@ -86,10 +86,11 @@ def payload(test_session)
                 "sha" => test_session.git_commit_sha,
                 "test_level" => Ext::Test::ITR_TEST_SKIPPING_MODE,
                 "configurations" => {
-                  "os.platform" => test_session.os_platform,
-                  "os.arch" => test_session.os_architecture,
-                  "runtime.name" => test_session.runtime_name,
-                  "runtime.version" => test_session.runtime_version
+                  Ext::Test::TAG_OS_PLATFORM => test_session.os_platform,
+                  Ext::Test::TAG_OS_ARCHITECTURE => test_session.os_architecture,
+                  Ext::Test::TAG_OS_VERSION => test_session.os_version,
+                  Ext::Test::TAG_RUNTIME_NAME => test_session.runtime_name,
+                  Ext::Test::TAG_RUNTIME_VERSION => test_session.runtime_version
                 }
               }
             }
diff --git a/lib/datadog/ci/utils/test_run.rb b/lib/datadog/ci/utils/test_run.rb
index 1e41715e..65a4c0e3 100644
--- a/lib/datadog/ci/utils/test_run.rb
+++ b/lib/datadog/ci/utils/test_run.rb
@@ -9,6 +9,10 @@ def self.command
 
           @command = "#{$0} #{ARGV.join(" ")}"
         end
+
+        def self.test_full_name(test_name, suite)
+          "#{suite}.#{test_name}"
+        end
       end
     end
   end
diff --git a/sig/datadog/ci/ext/test.rbs b/sig/datadog/ci/ext/test.rbs
index 5b235a54..dc308af1 100644
--- a/sig/datadog/ci/ext/test.rbs
+++ b/sig/datadog/ci/ext/test.rbs
@@ -52,6 +52,8 @@ module Datadog
 
         TAG_OS_PLATFORM: "os.platform"
 
+        TAG_OS_VERSION: "os.version"
+
         TAG_RUNTIME_NAME: "runtime.name"
 
         TAG_RUNTIME_VERSION: "runtime.version"
diff --git a/sig/datadog/ci/itr/runner.rbs b/sig/datadog/ci/itr/runner.rbs
index 1e4f8b53..180d7aca 100644
--- a/sig/datadog/ci/itr/runner.rbs
+++ b/sig/datadog/ci/itr/runner.rbs
@@ -5,12 +5,16 @@ module Datadog
         @enabled: bool
         @test_skipping_enabled: bool
         @code_coverage_enabled: bool
-        @api: Datadog::CI::Transport::Api::Base?
+        @correlation_id: String
+        @skippable_tests: Array[Datadog::CI::ITR::Skippable::Test]
         @coverage_writer: Datadog::CI::ITR::Coverage::Writer?
 
-        def initialize: (?enabled: bool, coverage_writer: Datadog::CI::ITR::Coverage::Writer?) -> void
+        @api: Datadog::CI::Transport::Api::Base?
+        @dd_env: String?
+
+        def initialize: (dd_env: String?, ?enabled: bool, coverage_writer: Datadog::CI::ITR::Coverage::Writer?, api: Datadog::CI::Transport::Api::Base?) -> void
 
-        def configure: (Hash[String, untyped] remote_configuration, Datadog::CI::TestSession test_session) -> void
+        def configure: (Hash[String, untyped] remote_configuration, test_session: Datadog::CI::TestSession, git_tree_upload_worker: Datadog::CI::Worker) -> void
 
         def enabled?: () -> bool
 
@@ -33,6 +37,8 @@ module Datadog
         def write: (Datadog::CI::ITR::Coverage::Event event) -> void
 
         def ensure_test_source_covered: (String test_source_file, Hash[String, untyped] coverage) -> void
+
+        def fetch_skippable_tests: (test_session: Datadog::CI::TestSession, git_tree_upload_worker: Datadog::CI::Worker) -> void
       end
     end
   end
diff --git a/sig/datadog/ci/itr/skippable.rbs b/sig/datadog/ci/itr/skippable.rbs
index bb06b5e9..15c81922 100644
--- a/sig/datadog/ci/itr/skippable.rbs
+++ b/sig/datadog/ci/itr/skippable.rbs
@@ -5,18 +5,6 @@ module Datadog
         @api: Datadog::CI::Transport::Api::Base?
         @dd_env: String?
 
-        class Test
-          @name: String?
-
-          @suite: String?
-
-          attr_reader name: String?
-
-          attr_reader suite: String?
-
-          def initialize: (name: String?, suite: String?) -> void
-        end
-
         class Response
           @http_response: Datadog::Core::Transport::HTTP::Adapters::Net::Response?
           @json: Hash[String, untyped]?
@@ -27,14 +15,14 @@ module Datadog
 
           def correlation_id: () -> String?
 
-          def tests: () -> Array[Test]
+          def tests: () -> Set[String]
 
           private
 
           def payload: () -> Hash[String, untyped]
         end
 
-        def initialize: (?api: Datadog::CI::Transport::Api::Base?, ?dd_env: String?) -> void
+        def initialize: (?api: Datadog::CI::Transport::Api::Base?, dd_env: String?) -> void
 
         def fetch_skippable_tests: (Datadog::CI::TestSession test_session) -> Response
 
diff --git a/sig/datadog/ci/span.rbs b/sig/datadog/ci/span.rbs
index cbf14fff..6be70c73 100644
--- a/sig/datadog/ci/span.rbs
+++ b/sig/datadog/ci/span.rbs
@@ -55,6 +55,8 @@ module Datadog
 
       def os_platform: () -> String?
 
+      def os_version: () -> String?
+
       def runtime_name: () -> String?
 
       def runtime_version: () -> String?
diff --git a/sig/datadog/ci/test_visibility/transport.rbs b/sig/datadog/ci/test_visibility/transport.rbs
index 7eeba0b0..77ec7a0b 100644
--- a/sig/datadog/ci/test_visibility/transport.rbs
+++ b/sig/datadog/ci/test_visibility/transport.rbs
@@ -10,7 +10,7 @@ module Datadog
 
         def initialize: (
           api: Datadog::CI::Transport::Api::Base,
-          ?dd_env: ::String?,
+          dd_env: ::String?,
           ?serializers_factory: singleton(Datadog::CI::TestVisibility::Serializers::Factories::TestLevel) | singleton(Datadog::CI::TestVisibility::Serializers::Factories::TestSuiteLevel),
           ?max_payload_size: Integer
         ) -> void
diff --git a/sig/datadog/ci/transport/http.rbs b/sig/datadog/ci/transport/http.rbs
index 9b02cebb..69154763 100644
--- a/sig/datadog/ci/transport/http.rbs
+++ b/sig/datadog/ci/transport/http.rbs
@@ -14,10 +14,12 @@ module Datadog
         attr_reader compress: bool
 
         DEFAULT_TIMEOUT: 30
+        MAX_RETRIES: 3
+        INITIAL_BACKOFF: 1
 
         def initialize: (host: String, ?port: Integer?, ?ssl: bool, ?timeout: Integer, ?compress: bool) -> void
 
-        def request: (?verb: String, payload: String, headers: Hash[String, String], path: String) -> ResponseDecorator
+        def request: (?verb: String, payload: String, headers: Hash[String, String], path: String, ?retries: Integer, ?backoff: Integer) -> ResponseDecorator
 
         private
 
@@ -25,6 +27,8 @@ module Datadog
 
         def build_env: (payload: String, headers: Hash[String, String], path: String, verb: String) -> Datadog::Core::Transport::HTTP::Env
 
+        def perform_http_call: (payload: String, headers: Hash[String, String], path: String, verb: String, ?retries: Integer, ?backoff: Integer) -> Datadog::Core::Transport::Response
+
         class AdapterSettings
           attr_reader hostname: String
           attr_reader port: Integer?
diff --git a/sig/datadog/ci/transport/remote_settings_api.rbs b/sig/datadog/ci/transport/remote_settings_api.rbs
index 15086cc4..1c655f0e 100644
--- a/sig/datadog/ci/transport/remote_settings_api.rbs
+++ b/sig/datadog/ci/transport/remote_settings_api.rbs
@@ -22,7 +22,7 @@ module Datadog
         @api: Datadog::CI::Transport::Api::Base?
         @dd_env: String?
 
-        def initialize: (?api: Datadog::CI::Transport::Api::Base?, ?dd_env: String?) -> void
+        def initialize: (?api: Datadog::CI::Transport::Api::Base?, dd_env: String?) -> void
 
         def fetch_library_settings: (Datadog::CI::TestSession test_session) -> Response
 
diff --git a/sig/datadog/ci/utils/test_run.rbs b/sig/datadog/ci/utils/test_run.rbs
index c985f99b..66fef457 100644
--- a/sig/datadog/ci/utils/test_run.rbs
+++ b/sig/datadog/ci/utils/test_run.rbs
@@ -5,6 +5,8 @@ module Datadog
         self.@command: String
 
         def self.command: () -> String
+
+        def self.test_full_name: (String test_name, String test_suite) -> String
       end
     end
   end
diff --git a/spec/datadog/ci/itr/runner_spec.rb b/spec/datadog/ci/itr/runner_spec.rb
index 80add74d..6fd53fd5 100644
--- a/spec/datadog/ci/itr/runner_spec.rb
+++ b/spec/datadog/ci/itr/runner_spec.rb
@@ -4,34 +4,41 @@
 
 RSpec.describe Datadog::CI::ITR::Runner do
   let(:itr_enabled) { true }
+
+  let(:api) { double("api") }
   let(:writer) { spy("writer") }
+  let(:git_worker) { spy("git_worker") }
+
   let(:tracer_span) { Datadog::Tracing::SpanOperation.new("session") }
   let(:test_session) { Datadog::CI::TestSession.new(tracer_span) }
 
-  subject(:runner) { described_class.new(coverage_writer: writer, enabled: itr_enabled) }
+  subject(:runner) { described_class.new(api: api, dd_env: "dd_env", coverage_writer: writer, enabled: itr_enabled) }
+  let(:configure) { runner.configure(remote_configuration, test_session: test_session, git_tree_upload_worker: git_worker) }
 
   before do
     allow(writer).to receive(:write)
   end
 
   describe "#configure" do
-    before do
-      runner.configure(remote_configuration, test_session)
-    end
-
     context "when remote configuration call failed" do
       let(:remote_configuration) { {"itr_enabled" => false} }
 
       it "configures the runner and test session" do
+        configure
+
         expect(runner.enabled?).to be false
         expect(runner.skipping_tests?).to be false
         expect(runner.code_coverage?).to be false
       end
     end
 
-    context "when remote configuration call returned correct response" do
+    context "when remote configuration call returned correct response without tests skipping" do
       let(:remote_configuration) { {"itr_enabled" => true, "code_coverage" => true, "tests_skipping" => false} }
 
+      before do
+        configure
+      end
+
       it "configures the runner" do
         expect(runner.enabled?).to be true
         expect(runner.skipping_tests?).to be false
@@ -47,10 +54,41 @@
       end
     end
 
+    context "when remote configuration call returned correct response with tests skipping" do
+      let(:remote_configuration) { {"itr_enabled" => true, "code_coverage" => true, "tests_skipping" => true} }
+      let(:skippable) do
+        instance_double(
+          Datadog::CI::ITR::Skippable,
+          fetch_skippable_tests: instance_double(
+            Datadog::CI::ITR::Skippable::Response,
+            correlation_id: "42",
+            tests: Set.new(["suite.test"])
+          )
+        )
+      end
+
+      before do
+        expect(Datadog::CI::ITR::Skippable).to receive(:new).and_return(skippable)
+        configure
+      end
+
+      it "configures the runner" do
+        expect(runner.enabled?).to be true
+        expect(runner.skipping_tests?).to be true
+
+        expect(runner.correlation_id).to eq("42")
+        expect(runner.skippable_tests).to eq(Set.new(["suite.test"]))
+
+        expect(git_worker).to have_received(:wait_until_done)
+      end
+    end
+
     context "when remote configuration call returned correct response with strings instead of bools" do
       let(:remote_configuration) { {"itr_enabled" => "true", "code_coverage" => "true", "tests_skipping" => "false"} }
 
       it "configures the runner" do
+        configure
+
         expect(runner.enabled?).to be true
         expect(runner.skipping_tests?).to be false
         expect(runner.code_coverage?).to be(!PlatformHelpers.jruby?) # code coverage is not supported in JRuby
@@ -61,6 +99,8 @@
       let(:remote_configuration) { {} }
 
       it "configures the runner" do
+        configure
+
         expect(runner.enabled?).to be false
         expect(runner.skipping_tests?).to be false
         expect(runner.code_coverage?).to be false
@@ -73,7 +113,7 @@
     let(:test_span) { Datadog::CI::Test.new(tracer_span) }
 
     before do
-      runner.configure(remote_configuration, test_session)
+      configure
     end
 
     context "when code coverage is disabled" do
@@ -140,7 +180,8 @@
     before do
       skip("Code coverage is not supported in JRuby") if PlatformHelpers.jruby?
 
-      runner.configure(remote_configuration, test_session)
+      configure
+
       expect(test_span).to receive(:id).and_return(1)
       expect(test_span).to receive(:test_suite_id).and_return(2)
       expect(test_span).to receive(:test_session_id).and_return(3)
diff --git a/spec/datadog/ci/itr/skippable_spec.rb b/spec/datadog/ci/itr/skippable_spec.rb
index be209ba5..32bef886 100644
--- a/spec/datadog/ci/itr/skippable_spec.rb
+++ b/spec/datadog/ci/itr/skippable_spec.rb
@@ -18,6 +18,7 @@
           "git.commit.sha" => "commit_sha",
           "os.platform" => "platform",
           "os.architecture" => "arch",
+          "os.version" => "version",
           "runtime.name" => "runtime_name",
           "runtime.version" => "runtime_version"
         })
@@ -47,6 +48,7 @@
         configurations = attributes["configurations"]
         expect(configurations["os.platform"]).to eq("platform")
         expect(configurations["os.architecture"]).to eq("arch")
+        expect(configurations["os.version"]).to eq("version")
         expect(configurations["runtime.name"]).to eq("runtime_name")
         expect(configurations["runtime.version"]).to eq("runtime_version")
       end
@@ -94,9 +96,7 @@
           it "parses the response" do
             expect(response.ok?).to be true
             expect(response.correlation_id).to eq("correlation_id_123")
-            expect(response.tests.first).to eq(
-              Datadog::CI::ITR::Skippable::Test.new(name: "test_name", suite: "test_suite_name")
-            )
+            expect(response.tests).to eq(Set.new(["test_suite_name.test_name"]))
           end
         end
 
diff --git a/spec/datadog/ci/span_spec.rb b/spec/datadog/ci/span_spec.rb
index b7709d34..c352f2f3 100644
--- a/spec/datadog/ci/span_spec.rb
+++ b/spec/datadog/ci/span_spec.rb
@@ -191,6 +191,7 @@
     it "sets the environment runtime tags" do
       expect(tracer_span).to receive(:set_tag).with("os.architecture", ::RbConfig::CONFIG["host_cpu"])
       expect(tracer_span).to receive(:set_tag).with("os.platform", ::RbConfig::CONFIG["host_os"])
+      expect(tracer_span).to receive(:set_tag).with("os.version", Datadog::Core::Environment::Platform.kernel_release)
       expect(tracer_span).to receive(:set_tag).with("runtime.name", Datadog::Core::Environment::Ext::LANG_ENGINE)
       expect(tracer_span).to receive(:set_tag).with("runtime.version", Datadog::Core::Environment::Ext::ENGINE_VERSION)
       expect(tracer_span).to receive(:set_tag).with("test.command", test_command)
@@ -253,6 +254,14 @@
     end
   end
 
+  describe "#os_version" do
+    it "returns the OS version" do
+      expect(tracer_span).to receive(:get_tag).with("os.version").and_return("version")
+
+      expect(span.os_version).to eq("version")
+    end
+  end
+
   describe "#runtime_name" do
     it "returns the runtime name" do
       expect(tracer_span).to receive(:get_tag).with("runtime.name").and_return("name")
diff --git a/spec/datadog/ci/transport/http_spec.rb b/spec/datadog/ci/transport/http_spec.rb
index f9e6cf5b..e9eca4d6 100644
--- a/spec/datadog/ci/transport/http_spec.rb
+++ b/spec/datadog/ci/transport/http_spec.rb
@@ -145,5 +145,32 @@
         expect(response.code).to eq(200)
       end
     end
+
+    context "when request fails" do
+      let(:request_options) { {backoff: 0} }
+
+      context "when succeeds after retries" do
+        before do
+          expect(adapter).to receive(:call).and_raise(Errno::ECONNRESET).exactly(described_class::MAX_RETRIES).times
+          expect(adapter).to receive(:call).and_return(http_response)
+        end
+
+        it "produces a response" do
+          is_expected.to be_a_kind_of(described_class::ResponseDecorator)
+
+          expect(response.code).to eq(200)
+        end
+      end
+
+      context "when retries are exhausted" do
+        before do
+          expect(adapter).to receive(:call).and_raise(Errno::ECONNRESET).exactly(described_class::MAX_RETRIES + 1).times
+        end
+
+        it "raises" do
+          expect { response }.to raise_error(Errno::ECONNRESET)
+        end
+      end
+    end
   end
 end
diff --git a/spec/datadog/ci/transport/remote_settings_api_spec.rb b/spec/datadog/ci/transport/remote_settings_api_spec.rb
index a46f30c9..f9c52091 100644
--- a/spec/datadog/ci/transport/remote_settings_api_spec.rb
+++ b/spec/datadog/ci/transport/remote_settings_api_spec.rb
@@ -18,6 +18,7 @@
           "git.commit.sha" => "commit_sha",
           "os.platform" => "platform",
           "os.architecture" => "arch",
+          "os.version" => "version",
           "runtime.name" => "runtime_name",
           "runtime.version" => "runtime_version"
         })
@@ -48,7 +49,8 @@
 
         configurations = attributes["configurations"]
         expect(configurations["os.platform"]).to eq("platform")
-        expect(configurations["os.arch"]).to eq("arch")
+        expect(configurations["os.architecture"]).to eq("arch")
+        expect(configurations["os.version"]).to eq("version")
         expect(configurations["runtime.name"]).to eq("runtime_name")
         expect(configurations["runtime.version"]).to eq("runtime_version")
       end
diff --git a/spec/support/contexts/ci_mode.rb b/spec/support/contexts/ci_mode.rb
index 8f232668..54b02054 100644
--- a/spec/support/contexts/ci_mode.rb
+++ b/spec/support/contexts/ci_mode.rb
@@ -23,6 +23,18 @@
   let(:git_metadata_upload_enabled) { false }
   let(:require_git) { false }
 
+  let(:itr_correlation_id) { "itr_correlation_id" }
+  let(:itr_skippable_tests) { [] }
+
+  let(:skippable_tests_response) do
+    instance_double(
+      Datadog::CI::ITR::Skippable::Response,
+      ok?: true,
+      correlation_id: itr_correlation_id,
+      tests: itr_skippable_tests
+    )
+  end
+
   let(:recorder) { Datadog.send(:components).ci_recorder }
 
   before do
@@ -35,8 +47,8 @@
     allow(Datadog::CI::Utils::TestRun).to receive(:command).and_return(test_command)
 
     allow_any_instance_of(Datadog::CI::Transport::RemoteSettingsApi).to receive(:fetch_library_settings).and_return(
-      double(
-        "remote_settings_api_response",
+      instance_double(
+        Datadog::CI::Transport::RemoteSettingsApi::Response,
         payload: {
           "itr_enabled" => itr_enabled,
           "code_coverage" => code_coverage_enabled,
@@ -45,8 +57,8 @@
         require_git?: require_git
       ),
       # This is for the second call to fetch_library_settings
-      double(
-        "remote_settings_api_response",
+      instance_double(
+        Datadog::CI::Transport::RemoteSettingsApi::Response,
         payload: {
           "itr_enabled" => itr_enabled,
           "code_coverage" => !code_coverage_enabled,
@@ -55,7 +67,7 @@
         require_git?: !require_git
       )
     )
-
+    allow_any_instance_of(Datadog::CI::ITR::Skippable).to receive(:fetch_skippable_tests).and_return(skippable_tests_response)
     allow_any_instance_of(Datadog::CI::ITR::Coverage::Transport).to receive(:send_events).and_return([])
 
     Datadog.configure do |c|
diff --git a/vendor/rbs/ddtrace/0/datadog/core/environment/platform.rbs b/vendor/rbs/ddtrace/0/datadog/core/environment/platform.rbs
new file mode 100644
index 00000000..ebfd15d0
--- /dev/null
+++ b/vendor/rbs/ddtrace/0/datadog/core/environment/platform.rbs
@@ -0,0 +1,12 @@
+module Datadog
+  module Core
+    module Environment
+      module Platform
+        def self?.hostname: () -> (untyped | nil)
+        def self?.kernel_name: () -> untyped
+        def self?.kernel_release: () -> (untyped | untyped | nil)
+        def self?.kernel_version: () -> (untyped | nil)
+      end
+    end
+  end
+end