ddtrace 1.20.0 → 1.21.0

data/lib/datadog/core/transport/ext.rb

@@ -25,6 +25,8 @@ module Datadog
           HEADER_META_LANG = 'Datadog-Meta-Lang'
           HEADER_META_LANG_VERSION = 'Datadog-Meta-Lang-Version'
           HEADER_META_LANG_INTERPRETER = 'Datadog-Meta-Lang-Interpreter'
+          # Use for distinguishing between CRuby, JRuby, and TruffleRuby.
+          HEADER_META_LANG_INTERPRETER_VENDOR = 'Datadog-Meta-Lang-Interpreter-Vendor'
           HEADER_META_TRACER_VERSION = 'Datadog-Meta-Tracer-Version'
 
           # Header that prevents the Net::HTTP integration from tracing internal trace requests.

data/lib/datadog/core/utils/url.rb

@@ -0,0 +1,25 @@
+# frozen_string_literal: true
+
+require 'uri'
+
+module Datadog
+  module Core
+    module Utils
+      # Helpers class that provides methods to process URLs
+      # such as filtering sensitive information.
+      module Url
+        def self.filter_basic_auth(url)
+          return nil if url.nil?
+
+          URI(url).tap do |u|
+            u.user = nil
+            u.password = nil
+          end.to_s
+        # Git scheme: git@github.com:DataDog/dd-trace-rb.git
+        rescue URI::InvalidURIError
+          url
+        end
+      end
+    end
+  end
+end

data/lib/datadog/profiling/collectors/cpu_and_wall_time_worker.rb

@@ -100,6 +100,12 @@ module Datadog
         def stats
           self.class._native_stats(self)
         end
+
+        def stats_and_reset_not_thread_safe
+          stats = self.stats
+          self.class._native_stats_reset_not_thread_safe(self)
+          stats
+        end
       end
     end
   end

data/lib/datadog/profiling/collectors/info.rb

@@ -0,0 +1,101 @@
+# frozen_string_literal: true
+
+require 'set'
+require 'time'
+
+module Datadog
+  module Profiling
+    module Collectors
+      # Collects information of relevance for profiler. This will get sent alongside
+      # the profile and show up in the UI or potentially influence processing in some way.
+      #
+      # Information is currently collected and frozen at construction time. A full collector
+      # could be seen as overkill for this case but it allows us to centralize information
+      # gathering and easily support more flexible/dynamic info collection in the future.
+      class Info
+        def initialize(settings)
+          @profiler_info = nil
+          @info = {
+            platform: collect_platform_info,
+            runtime: collect_runtime_info,
+            application: collect_application_info(settings),
+            profiler: collect_profiler_info(settings),
+          }.freeze
+        end
+
+        attr_reader :info
+
+        private
+
+        # Instead of trying to figure out real process start time by checking
+        # /proc or some other complex/non-portable way, approximate start time
+        # by time of requirement of this file.
+        START_TIME = Time.now.utc.freeze
+
+        def collect_platform_info
+          @platform_info ||= {
+            container_id: Datadog::Core::Environment::Container.container_id,
+            hostname: Datadog::Core::Environment::Platform.hostname,
+            kernel_name: Datadog::Core::Environment::Platform.kernel_name,
+            kernel_release: Datadog::Core::Environment::Platform.kernel_release,
+            kernel_version: Datadog::Core::Environment::Platform.kernel_version
+          }.freeze
+        end
+
+        def collect_runtime_info
+          @runtime_info ||= {
+            engine: Datadog::Core::Environment::Identity.lang_engine,
+            version: Datadog::Core::Environment::Identity.lang_version,
+            platform: Datadog::Core::Environment::Identity.lang_platform,
+          }.freeze
+        end
+
+        def collect_application_info(settings)
+          @application_info ||= {
+            start_time: START_TIME.iso8601,
+            env: settings.env,
+            service: settings.service,
+            version: settings.version,
+          }.freeze
+        end
+
+        def collect_profiler_info(settings)
+          unless @profiler_info
+            lib_datadog_gem = ::Gem.loaded_specs['libdatadog']
+            @profiler_info = {
+              version: Datadog::Core::Environment::Identity.tracer_version,
+              libdatadog: "#{lib_datadog_gem.version}-#{lib_datadog_gem.platform}",
+              settings: collect_settings_recursively(settings.profiling),
+            }.freeze
+          end
+          @profiler_info
+        end
+
+        # The settings/option model isn't directly serializable because
+        # of subsettings and options that link to full blown custom object
+        # instances without proper serialization.
+        # This method navigates a settings object recursively, converting
+        # it into more basic types that are trivially convertible to JSON.
+        def collect_settings_recursively(v)
+          v = v.options_hash if v.respond_to?(:options_hash)
+
+          if v.nil? || v.is_a?(Symbol) || v.is_a?(Numeric) || v.is_a?(String) || v.equal?(true) || v.equal?(false)
+            Core::Utils::SafeDup.frozen_or_dup(v)
+          elsif v.is_a?(Hash)
+            collected_hash = v.each_with_object({}) do |(key, value), hash|
+              collected_value = collect_settings_recursively(value)
+              hash[key] = collected_value
+            end
+            collected_hash.freeze
+          elsif v.is_a?(Enumerable)
+            collected_list = v
+              .map { |value| collect_settings_recursively(value) }
+            collected_list.freeze
+          else
+            v.inspect
+          end
+        end
+      end
+    end
+  end
+end

data/lib/datadog/profiling/component.rb

@@ -8,11 +8,7 @@ module Datadog
       # * Code Hotspots panel in the trace viewer, as well as scoping a profile down to a span
       # * Endpoint aggregation in the profiler UX, including normalization (resource per endpoint call)
       def self.build_profiler_component(settings:, agent_settings:, optional_tracer:) # rubocop:disable Metrics/MethodLength
-        require_relative '../profiling/diagnostics/environment_logger'
-
-        Profiling::Diagnostics::EnvironmentLogger.collect_and_log!
-
-        return unless settings.profiling.enabled
+        return [nil, { profiling_enabled: false }] unless settings.profiling.enabled
 
         # Workaround for weird dependency direction: the Core::Configuration::Components class currently has a
         # dependency on individual products, in this case the Profiler.
@@ -32,7 +28,8 @@ module Datadog
         # done, then profiling may not be loaded, and thus to avoid this issue we do a require here (which is a
         # no-op if profiling is already loaded).
         require_relative '../profiling'
-        return unless Profiling.supported?
+
+        return [nil, { profiling_enabled: false }] unless Profiling.supported?
 
         # Activate forking extensions
         Profiling::Tasks::Setup.new.run
@@ -40,7 +37,7 @@ module Datadog
         # NOTE: Please update the Initialization section of ProfilingDevelopment.md with any changes to this method
 
         no_signals_workaround_enabled = no_signals_workaround_enabled?(settings)
-        timeline_enabled = settings.profiling.advanced.experimental_timeline_enabled
+        timeline_enabled = settings.profiling.advanced.timeline_enabled
         allocation_profiling_enabled = enable_allocation_profiling?(settings)
         heap_sample_every = get_heap_sample_every(settings)
         heap_profiling_enabled = enable_heap_profiling?(settings, allocation_profiling_enabled, heap_sample_every)
@@ -72,11 +69,11 @@ module Datadog
           heap_sample_every: heap_sample_every,
         }.freeze
 
-        exporter = build_profiler_exporter(settings, recorder, internal_metadata: internal_metadata)
+        exporter = build_profiler_exporter(settings, recorder, worker, internal_metadata: internal_metadata)
         transport = build_profiler_transport(settings, agent_settings)
         scheduler = Profiling::Scheduler.new(exporter: exporter, transport: transport, interval: upload_period_seconds)
 
-        Profiling::Profiler.new(worker: worker, scheduler: scheduler)
+        [Profiling::Profiler.new(worker: worker, scheduler: scheduler), { profiling_enabled: true }]
       end
 
       private_class_method def self.build_thread_context_collector(settings, recorder, optional_tracer, timeline_enabled)
@@ -89,12 +86,15 @@ module Datadog
         )
       end
 
-      private_class_method def self.build_profiler_exporter(settings, recorder, internal_metadata:)
+      private_class_method def self.build_profiler_exporter(settings, recorder, worker, internal_metadata:)
+        info_collector = Profiling::Collectors::Info.new(settings)
         code_provenance_collector =
           (Profiling::Collectors::CodeProvenance.new if settings.profiling.advanced.code_provenance_enabled)
 
         Profiling::Exporter.new(
           pprof_recorder: recorder,
+          worker: worker,
+          info_collector: info_collector,
           code_provenance_collector: code_provenance_collector,
           internal_metadata: internal_metadata,
         )
@@ -135,7 +135,7 @@ module Datadog
       end
 
       private_class_method def self.enable_allocation_profiling?(settings)
-        unless settings.profiling.advanced.experimental_allocation_enabled
+        unless settings.profiling.allocation_enabled
           # Allocation profiling disabled, short-circuit out
           return false
         end
@@ -179,9 +179,7 @@ module Datadog
           )
         end
 
-        Datadog.logger.warn(
-          'Enabled experimental allocation profiling. This is experimental, not recommended, and will increase overhead!'
-        )
+        Datadog.logger.debug('Enabled allocation profiling')
 
         true
       end

data/lib/datadog/profiling/exporter.rb

@@ -23,31 +23,39 @@ module Datadog
         :time_provider,
         :last_flush_finish_at,
         :created_at,
-        :internal_metadata
+        :internal_metadata,
+        :info_json
 
       public
 
       def initialize(
         pprof_recorder:,
+        worker:,
+        info_collector:,
         code_provenance_collector:,
         internal_metadata:,
         minimum_duration_seconds: PROFILE_DURATION_THRESHOLD_SECONDS,
         time_provider: Time
       )
         @pprof_recorder = pprof_recorder
+        @worker = worker
         @code_provenance_collector = code_provenance_collector
         @minimum_duration_seconds = minimum_duration_seconds
         @time_provider = time_provider
         @last_flush_finish_at = nil
         @created_at = time_provider.now.utc
         @internal_metadata = internal_metadata
+        # NOTE: At the time of this comment collected info does not change over time so we'll hardcode
+        #       it on startup to prevent serializing the same info on every flush.
+        @info_json = JSON.fast_generate(info_collector.info).freeze
       end
 
       def flush
-        start, finish, uncompressed_pprof = pprof_recorder.serialize
+        worker_stats = @worker.stats_and_reset_not_thread_safe
+        start, finish, compressed_pprof = pprof_recorder.serialize
         @last_flush_finish_at = finish
 
-        return if uncompressed_pprof.nil? # We don't want to report empty profiles
+        return if compressed_pprof.nil? # We don't want to report empty profiles
 
         if duration_below_threshold?(start, finish)
           Datadog.logger.debug('Skipped exporting profiling events as profile duration is below minimum')
@@ -60,11 +68,17 @@ module Datadog
           start: start,
           finish: finish,
           pprof_file_name: Datadog::Profiling::Ext::Transport::HTTP::PPROF_DEFAULT_FILENAME,
-          pprof_data: uncompressed_pprof.to_s,
+          pprof_data: compressed_pprof.to_s,
           code_provenance_file_name: Datadog::Profiling::Ext::Transport::HTTP::CODE_PROVENANCE_FILENAME,
           code_provenance_data: uncompressed_code_provenance,
           tags_as_array: Datadog::Profiling::TagBuilder.call(settings: Datadog.configuration).to_a,
-          internal_metadata: internal_metadata,
+          internal_metadata: internal_metadata.merge(
+            {
+              worker_stats: worker_stats,
+              gc: GC.stat,
+            }
+          ),
+          info_json: info_json,
         )
       end
 

data/lib/datadog/profiling/ext.rb

@@ -23,6 +23,8 @@ module Datadog
           FORM_FIELD_TAG_RUNTIME_VERSION = 'runtime_version'
           FORM_FIELD_TAG_SERVICE = 'service'
           FORM_FIELD_TAG_VERSION = 'version'
+          TAG_GIT_REPOSITORY_URL = 'git.repository_url'
+          TAG_GIT_COMMIT_SHA = 'git.commit.sha'
 
           PPROF_DEFAULT_FILENAME = 'rubyprofile.pprof'
           CODE_PROVENANCE_FILENAME = 'code-provenance.json'

data/lib/datadog/profiling/flush.rb

@@ -14,7 +14,8 @@ module Datadog
         :code_provenance_file_name,
         :code_provenance_data, # gzipped json bytes
         :tags_as_array,
-        :internal_metadata_json
+        :internal_metadata_json,
+        :info_json
 
       def initialize(
         start:,
@@ -24,7 +25,8 @@ module Datadog
         code_provenance_file_name:,
         code_provenance_data:,
         tags_as_array:,
-        internal_metadata:
+        internal_metadata:,
+        info_json:
       )
         @start = start
         @finish = finish
@@ -33,7 +35,8 @@ module Datadog
         @code_provenance_file_name = code_provenance_file_name
         @code_provenance_data = code_provenance_data
         @tags_as_array = tags_as_array
-        @internal_metadata_json = JSON.fast_generate(internal_metadata.map { |k, v| [k, v.to_s] }.to_h)
+        @internal_metadata_json = JSON.fast_generate(internal_metadata)
+        @info_json = info_json
       end
     end
   end

data/lib/datadog/profiling/http_transport.rb

@@ -43,6 +43,8 @@ module Datadog
 
           tags_as_array: flush.tags_as_array,
           internal_metadata_json: flush.internal_metadata_json,
+
+          info_json: flush.info_json
         )
 
         if status == :ok
@@ -117,7 +119,8 @@ module Datadog
         code_provenance_file_name:,
         code_provenance_data:,
         tags_as_array:,
-        internal_metadata_json:
+        internal_metadata_json:,
+        info_json:
       )
         self.class._native_do_export(
           exporter_configuration,
@@ -132,6 +135,7 @@ module Datadog
           code_provenance_data,
           tags_as_array,
           internal_metadata_json,
+          info_json,
         )
       end
 

data/lib/datadog/profiling/load_native_extension.rb

@@ -1,23 +1,23 @@
 # This file is used to load the profiling native extension. It works in two steps:
 #
-# 1. Load the ddtrace_profiling_loader extension. This extension will be used to load the actual extension, but in
-#    a special way that avoids exposing native-level code symbols. See `ddtrace_profiling_loader.c` for more details.
+# 1. Load the datadog_profiling_loader extension. This extension will be used to load the actual extension, but in
+#    a special way that avoids exposing native-level code symbols. See `datadog_profiling_loader.c` for more details.
 #
-# 2. Use the Datadog::Profiling::Loader exposed by the ddtrace_profiling_loader extension to load the actual
+# 2. Use the Datadog::Profiling::Loader exposed by the datadog_profiling_loader extension to load the actual
 #    profiling native extension.
 #
 # All code on this file is on-purpose at the top-level; this makes it so this file is executed only once,
 # the first time it gets required, to avoid any issues with the native extension being initialized more than once.
 
 begin
-  require "ddtrace_profiling_loader.#{RUBY_VERSION}_#{RUBY_PLATFORM}"
+  require "datadog_profiling_loader.#{RUBY_VERSION}_#{RUBY_PLATFORM}"
 rescue LoadError => e
   raise LoadError,
     'Failed to load the profiling loader extension. To fix this, please remove and then reinstall ddtrace ' \
     "(Details: #{e.message})"
 end
 
-extension_name = "ddtrace_profiling_native_extension.#{RUBY_VERSION}_#{RUBY_PLATFORM}"
+extension_name = "datadog_profiling_native_extension.#{RUBY_VERSION}_#{RUBY_PLATFORM}"
 full_file_path = "#{__dir__}/../../#{extension_name}.#{RbConfig::CONFIG['DLEXT']}"
 init_function_name = "Init_#{extension_name.split('.').first}"
 

data/lib/datadog/profiling/native_extension.rb

@@ -3,7 +3,7 @@
 module Datadog
   module Profiling
     # This module contains classes and methods which are implemented using native code in the
-    # ext/ddtrace_profiling_native_extension folder, as well as some Ruby-level utilities that don't make sense to
+    # ext/datadog_profiling_native_extension folder, as well as some Ruby-level utilities that don't make sense to
     # write using C
     module NativeExtension
       private_class_method def self.working?

data/lib/datadog/profiling/tag_builder.rb

@@ -1,6 +1,7 @@
 # frozen_string_literal: true
 
 require_relative '../core/utils'
+require_relative '../core/environment/git'
 
 module Datadog
   module Profiling
@@ -23,6 +24,8 @@ module Datadog
         runtime_id: Core::Environment::Identity.id,
         runtime_platform: Core::Environment::Identity.lang_platform,
         runtime_version: Core::Environment::Identity.lang_version,
+        git_repository_url: Core::Environment::Git.git_repository_url,
+        git_commit_sha: Core::Environment::Git.git_commit_sha,
         # User-provided tags
         user_tags: settings.tags
       )
@@ -42,6 +45,8 @@ module Datadog
         tags[FORM_FIELD_TAG_ENV] = env if env
         tags[FORM_FIELD_TAG_SERVICE] = service if service
         tags[FORM_FIELD_TAG_VERSION] = version if version
+        tags[TAG_GIT_REPOSITORY_URL] = git_repository_url if git_repository_url
+        tags[TAG_GIT_COMMIT_SHA] = git_commit_sha if git_commit_sha
 
         # Make sure everything is an utf-8 string, to avoid encoding issues in native code/libddprof/further downstream
         user_tags.merge(tags).map do |key, value|

data/lib/datadog/profiling/tasks/exec.rb

@@ -1,7 +1,7 @@
 module Datadog
   module Profiling
     module Tasks
-      # Wraps command with Datadog tracing
+      # Wraps command with Datadog profiling
       class Exec
         attr_reader :args
 
@@ -36,10 +36,10 @@ module Datadog
         def exec_with_error_handling(args)
           Kernel.exec(*args)
         rescue Errno::ENOENT => e
-          Kernel.warn "ddtracerb exec failed: #{e.class.name} #{e.message} (command was '#{args.join(' ')}')"
+          Kernel.warn "ddprofrb exec failed: #{e.class.name} #{e.message} (command was '#{args.join(' ')}')"
           Kernel.exit 127
         rescue Errno::EACCES, Errno::ENOEXEC => e
-          Kernel.warn "ddtracerb exec failed: #{e.class.name} #{e.message} (command was '#{args.join(' ')}')"
+          Kernel.warn "ddprofrb exec failed: #{e.class.name} #{e.message} (command was '#{args.join(' ')}')"
           Kernel.exit 126
         end
       end

data/lib/datadog/profiling/tasks/help.rb

@@ -1,12 +1,12 @@
 module Datadog
   module Profiling
     module Tasks
-      # Prints help message for usage of `ddtrace`
+      # Prints help message for usage of `ddprofrb`
       class Help
         def run
           puts %(
-  Usage: ddtracerb [command] [arguments]
-    exec [command]: Executes command with tracing & profiling preloaded.
+  Usage: ddprofrb [command] [arguments]
+    exec [command]: Executes command with profiling preloaded.
     help:           Prints this help message.
           )
         end

data/lib/datadog/profiling.rb

@@ -77,7 +77,7 @@ module Datadog
 
     private_class_method def self.try_reading_skipped_reason_file(file_api = File)
       # This file, if it exists, is recorded by extconf.rb during compilation of the native extension
-      skipped_reason_file = "#{__dir__}/../../ext/ddtrace_profiling_native_extension/skipped_reason.txt"
+      skipped_reason_file = "#{__dir__}/../../ext/datadog_profiling_native_extension/skipped_reason.txt"
 
       begin
         return unless file_api.exist?(skipped_reason_file)
@@ -123,13 +123,13 @@ module Datadog
       return false unless supported?
 
       require_relative 'profiling/ext/forking'
+      require_relative 'profiling/collectors/info'
       require_relative 'profiling/collectors/code_provenance'
       require_relative 'profiling/collectors/cpu_and_wall_time_worker'
       require_relative 'profiling/collectors/dynamic_sampling_rate'
       require_relative 'profiling/collectors/idle_sampling_helper'
       require_relative 'profiling/collectors/stack'
       require_relative 'profiling/collectors/thread_context'
-      require_relative 'profiling/diagnostics/environment_logger'
       require_relative 'profiling/stack_recorder'
       require_relative 'profiling/exporter'
       require_relative 'profiling/flush'

data/lib/datadog/tracing/contrib/concurrent_ruby/async_patch.rb

@@ -0,0 +1,20 @@
+# frozen_string_literal: true
+
+require_relative 'context_composite_executor_service'
+
+module Datadog
+  module Tracing
+    module Contrib
+      module ConcurrentRuby
+        # This patches the Async - to wrap executor service using ContextCompositeExecutorService
+        module AsyncPatch
+          def initialize(delegate)
+            super(delegate)
+
+            @executor = ContextCompositeExecutorService.new(@executor)
+          end
+        end
+      end
+    end
+  end
+end

data/lib/datadog/tracing/contrib/concurrent_ruby/patcher.rb

@@ -6,7 +6,7 @@ module Datadog
   module Tracing
     module Contrib
       module ConcurrentRuby
-        # Patcher enables patching of 'Future' class.
+        # Patcher enables patching of 'Future' and 'Async' classes.
         module Patcher
           include Contrib::Patcher
 
@@ -21,6 +21,16 @@ module Datadog
             patch_future
             require_relative 'promises_future_patch'
             patch_promises_future
+            require_relative 'async_patch'
+            async_patch
+          end
+
+          # Propagate tracing context in Concurrent::Async
+          def async_patch
+            if defined?(::Concurrent::Async)
+              # NOTE: AsyncDelegator is a private constant
+              ::Concurrent::Async.const_get(:AsyncDelegator).prepend(AsyncPatch)
+            end
           end
 
           # Propagate tracing context in Concurrent::Future

data/lib/datadog/tracing/contrib/extensions.rb

@@ -168,8 +168,12 @@ module Datadog
               integration
             end
 
-            # TODO: Deprecate in the next major version, as `instrument` better describes this method's purpose
-            alias_method :use, :instrument
+            def use(integration_name, options = {}, &block)
+              Core.log_deprecation do
+                'Configuration with `use` has been deprecated, use `instrument` instead.'
+              end
+              instrument(integration_name, options, &block)
+            end
 
             # For the provided `integration_name`, resolves a matching configuration
             # for the provided integration from an integration-specific `key`.

data/lib/datadog/tracing/contrib/grape/endpoint.rb

@@ -94,6 +94,8 @@ module Datadog
 
                 span.set_error(payload[:exception_object]) if exception_is_error?(payload[:exception_object])
 
+                integration_route = endpoint.env['grape.routing_args'][:route_info].pattern.origin
+
                 # override the current span with this notification values
                 span.set_tag(Ext::TAG_ROUTE_ENDPOINT, api_view) unless api_view.nil?
                 span.set_tag(Ext::TAG_ROUTE_PATH, path)
@@ -101,6 +103,9 @@ module Datadog
 
                 span.set_tag(Tracing::Metadata::Ext::HTTP::TAG_METHOD, request_method)
                 span.set_tag(Tracing::Metadata::Ext::HTTP::TAG_URL, path)
+
+                trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE, integration_route)
+                trace.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH, endpoint.env['SCRIPT_NAME'])
               ensure
                 span.start(start)
                 span.finish(finish)

data/lib/datadog/tracing/contrib/pg/instrumentation.rb

@@ -125,15 +125,22 @@ module Datadog
                 end
 
                 # Read metadata from PG::Result
+                #
+                # It is important to guard with `nil` check, because it is possible
+                # the result is `nil` instead of `PG::Result`.
+                #
+                # A non-null pointer will generally be returned except in out-of-memory conditions or
+                # serious errors such as inability to send the command to the server.
+                #
+                # see: https://www.postgresql.org/docs/current/libpq-exec.html#LIBPQ-PQEXEC
                 if block
                   yield(propagated_sql_statement, proc do |result|
-                    ret = block.call(result)
-                    annotate_span_with_result!(span, result)
-                    ret
+                    annotate_span_with_result!(span, result) if result
+                    block.call(result)
                   end)
                 else
                   result = yield(propagated_sql_statement)
-                  annotate_span_with_result!(span, result)
+                  annotate_span_with_result!(span, result) if result
                   result
                 end
               end

data/lib/datadog/tracing/contrib/rack/middlewares.rb

@@ -66,6 +66,10 @@ module Datadog
             end
           end
 
+          # rubocop:disable Metrics/CyclomaticComplexity
+          # rubocop:disable Metrics/PerceivedComplexity
+          # rubocop:disable Metrics/MethodLength
+          # rubocop:disable Metrics/AbcSize
           def call(env)
             # Find out if this is rack within rack
             previous_request_span = env[Ext::RACK_ENV_REQUEST_SPAN]
@@ -107,6 +111,30 @@ module Datadog
 
             # call the rest of the stack
             status, headers, response = @app.call(env)
+
+            if status != 404 && (last_route = request_trace.get_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE))
+              last_script_name = request_trace.get_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH)
+
+              # If the last_script_name is empty but the env['SCRIPT_NAME'] is NOT empty
+              # then the current rack request was not routed and must be accounted for
+              # which only happens in pure nested rack requests i.e /rack/rack/hello/world
+              #
+              # To account for the unaccounted nested rack requests of /rack/hello/world,
+              # we use 'PATH_INFO knowing that rack cannot have named parameters
+              if last_script_name == '' && env['SCRIPT_NAME'] != ''
+                last_script_name = last_route
+                last_route = env['PATH_INFO']
+              end
+
+              # Clear the route and route path tags from the request trace to avoid possibility of misplacement
+              request_trace.clear_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE)
+              request_trace.clear_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH)
+
+              # Ensure tags are placed in rack.request span as desired
+              request_span.set_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE, last_script_name + last_route)
+              request_span.clear_tag(Tracing::Metadata::Ext::HTTP::TAG_ROUTE_PATH)
+            end
+
             [status, headers, response]
 
           # rubocop:disable Lint/RescueException
@@ -142,10 +170,6 @@ module Datadog
           end
           # rubocop:enable Lint/RescueException
 
-          # rubocop:disable Metrics/AbcSize
-          # rubocop:disable Metrics/CyclomaticComplexity
-          # rubocop:disable Metrics/PerceivedComplexity
-          # rubocop:disable Metrics/MethodLength
           def set_request_tags!(trace, request_span, env, status, headers, response, original_env)
             request_header_collection = Header::RequestHeaderCollection.new(env)