From b4bd321dd77469419a124396581cbfa24e6b7c60 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Mon, 14 Apr 2025 12:29:54 +0000
Subject: [PATCH 1/8] [active_job] patch retry_job to report all errors during
 retries

---
 sentry-rails/lib/sentry/rails/active_job.rb      |  7 +++++++
 sentry-rails/spec/sentry/rails/activejob_spec.rb | 16 ++++++++++------
 2 files changed, 17 insertions(+), 6 deletions(-)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index 8fa1f8716..700d5f191 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -17,6 +17,13 @@ def already_supported_by_sentry_integration?
         Sentry.configuration.rails.skippable_job_adapters.include?(self.class.queue_adapter.class.to_s)
       end
 
+      def retry_job(error:, **opts)
+        unless Sentry.configuration.rails.active_job_report_after_job_retries
+          SentryReporter.capture_exception(self, error)
+        end
+        super
+      end
+
       class SentryReporter
         OP_NAME = "queue.active_job"
         SPAN_ORIGIN = "auto.queue.active_job"
diff --git a/sentry-rails/spec/sentry/rails/activejob_spec.rb b/sentry-rails/spec/sentry/rails/activejob_spec.rb
index 551a0be27..85b58df9b 100644
--- a/sentry-rails/spec/sentry/rails/activejob_spec.rb
+++ b/sentry-rails/spec/sentry/rails/activejob_spec.rb
@@ -446,9 +446,11 @@ def perform(event, hint)
         allow(Sentry::Rails::ActiveJobExtensions::SentryReporter)
           .to receive(:capture_exception).and_call_original
 
-        assert_performed_jobs 3 do
-          FailedJobWithRetryOn.perform_later rescue nil
-        end
+        FailedJobWithRetryOn.perform_later rescue nil
+
+        perform_enqueued_jobs
+        perform_enqueued_jobs
+        perform_enqueued_jobs rescue nil
 
         expect(Sentry::Rails::ActiveJobExtensions::SentryReporter)
           .to have_received(:capture_exception)
@@ -469,9 +471,11 @@ def perform(event, hint)
         allow(Sentry::Rails::ActiveJobExtensions::SentryReporter)
           .to receive(:capture_exception).and_call_original
 
-        assert_performed_jobs 3 do
-          FailedJobWithRetryOn.perform_later rescue nil
-        end
+        FailedJobWithRetryOn.perform_later rescue nil
+
+        perform_enqueued_jobs
+        perform_enqueued_jobs
+        perform_enqueued_jobs rescue nil
 
         expect(Sentry::Rails::ActiveJobExtensions::SentryReporter)
           .to have_received(:capture_exception)

From 00e34d1fb2187ed08b0d70ab3ba5cf5fc4dc4ee5 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Mon, 14 Apr 2025 12:47:05 +0000
Subject: [PATCH 2/8] [active_job] dry-up capturing logic a bit

---
 sentry-rails/lib/sentry/rails/active_job.rb | 14 ++++++++------
 1 file changed, 8 insertions(+), 6 deletions(-)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index 700d5f191..4a04c2977 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -18,9 +18,7 @@ def already_supported_by_sentry_integration?
       end
 
       def retry_job(error:, **opts)
-        unless Sentry.configuration.rails.active_job_report_after_job_retries
-          SentryReporter.capture_exception(self, error)
-        end
+        SentryReporter.maybe_capture_exception(self, error)
         super
       end
 
@@ -54,15 +52,19 @@ def record(job, &block)
               rescue Exception => e # rubocop:disable Lint/RescueException
                 finish_sentry_transaction(transaction, 500)
 
-                unless Sentry.configuration.rails.active_job_report_after_job_retries
-                  capture_exception(job, e)
-                end
+                maybe_capture_exception(job, e)
 
                 raise
               end
             end
           end
 
+          def maybe_capture_exception(job, e)
+            unless Sentry.configuration.rails.active_job_report_after_job_retries
+              capture_exception(job, e)
+            end
+          end
+
           def capture_exception(job, e)
             Sentry::Rails.capture_exception(
               e,

From 5d1cb2051c8591cd69d6e18d5fc968baa514a295 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Mon, 14 Apr 2025 12:55:43 +0000
Subject: [PATCH 3/8] Update CHANGELOG

---
 CHANGELOG.md | 1 +
 1 file changed, 1 insertion(+)

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8b0bcb716..72df9e0b2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,7 @@
   - Fixes [#2478](https://github.com/getsentry/sentry-ruby/issues/2478)
 - Fix compatibility issues with sidekiq-cron 2.2.0 ([#2591](https://github.com/getsentry/sentry-ruby/pull/2591))
 - Update sentry-sidekiq to work correctly with Sidekiq 8.0 and its new timestamp format ([#2570](https://github.com/getsentry/sentry-ruby/pull/2570))
+- Ensure we capture exceptions after each job retry ([#2597](https://github.com/getsentry/sentry-ruby/pull/2597))
 
 ### Internal
 

From 5930c153517348f04af71c45f1439060b7ebc70e Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Wed, 30 Apr 2025 11:08:03 +0000
Subject: [PATCH 4/8] Rework to use  event

---
 sentry-rails/lib/sentry/rails/active_job.rb | 24 ++++++++++++++++-----
 sentry-rails/lib/sentry/rails/railtie.rb    |  7 ++++--
 2 files changed, 24 insertions(+), 7 deletions(-)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index 4a04c2977..bf43649f3 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -17,11 +17,6 @@ def already_supported_by_sentry_integration?
         Sentry.configuration.rails.skippable_job_adapters.include?(self.class.queue_adapter.class.to_s)
       end
 
-      def retry_job(error:, **opts)
-        SentryReporter.maybe_capture_exception(self, error)
-        super
-      end
-
       class SentryReporter
         OP_NAME = "queue.active_job"
         SPAN_ORIGIN = "auto.queue.active_job"
@@ -76,6 +71,14 @@ def capture_exception(job, e)
             )
           end
 
+          def register_retry_subscriber
+            unless @retry_subscriber
+              @retry_subscriber = ActiveSupport::Notifications.subscribe("enqueue_retry.active_job") do |*args|
+                retry_handler(*args)
+              end
+            end
+          end
+
           def register_retry_stopped_subscriber
             unless @retry_stopped_subscriber
               @retry_stopped_subscriber = ActiveSupport::Notifications.subscribe(NOTIFICATION_NAME) do |*args|
@@ -91,6 +94,17 @@ def detach_retry_stopped_subscriber
             end
           end
 
+          def retry_handler(*args)
+            event = ActiveSupport::Notifications::Event.new(*args)
+            job = event.payload[:job]
+            error = event.payload[:error]
+
+            return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
+            return if Sentry.configuration.rails.active_job_report_after_job_retries
+
+            capture_exception(job, error)
+          end
+
           def retry_stopped_handler(*args)
             event = ActiveSupport::Notifications::Event.new(*args)
             job = event.payload[:job]
diff --git a/sentry-rails/lib/sentry/rails/railtie.rb b/sentry-rails/lib/sentry/rails/railtie.rb
index 2025c7c88..a31ae12df 100644
--- a/sentry-rails/lib/sentry/rails/railtie.rb
+++ b/sentry-rails/lib/sentry/rails/railtie.rb
@@ -53,7 +53,9 @@ class Railtie < ::Rails::Railtie
       register_error_subscriber(app) if ::Rails.version.to_f >= 7.0 && Sentry.configuration.rails.register_error_subscriber
 
       # Presence of ActiveJob is no longer a reliable cue
-      register_retry_stopped_subscriber if defined?(Sentry::Rails::ActiveJobExtensions)
+      if defined?(Sentry::Rails::ActiveJobExtensions)
+        register_active_job_subscribers
+      end
     end
 
     runner do
@@ -141,7 +143,8 @@ def register_error_subscriber(app)
       app.executor.error_reporter.subscribe(Sentry::Rails::ErrorSubscriber.new)
     end
 
-    def register_retry_stopped_subscriber
+    def register_active_job_subscribers
+      Sentry::Rails::ActiveJobExtensions::SentryReporter.register_retry_subscriber
       Sentry::Rails::ActiveJobExtensions::SentryReporter.register_retry_stopped_subscriber
     end
   end

From 3db0e7f4c40f346c4b4f154dcc9695bfcba23f59 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Wed, 30 Apr 2025 11:12:10 +0000
Subject: [PATCH 5/8] Detach retry_handler in specs

---
 sentry-rails/lib/sentry/rails/active_job.rb | 7 ++++++-
 sentry-rails/spec/spec_helper.rb            | 2 +-
 2 files changed, 7 insertions(+), 2 deletions(-)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index bf43649f3..0dcc2d930 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -87,11 +87,16 @@ def register_retry_stopped_subscriber
             end
           end
 
-          def detach_retry_stopped_subscriber
+          def detach_handlers
             if @retry_stopped_subscriber
               ActiveSupport::Notifications.unsubscribe(@retry_stopped_subscriber)
               @retry_stopped_subscriber = nil
             end
+
+            if @retry_handler
+              ActiveSupport::Notifications.unsubscribe(@retry_handler)
+              @retry_handler = nil
+            end
           end
 
           def retry_handler(*args)
diff --git a/sentry-rails/spec/spec_helper.rb b/sentry-rails/spec/spec_helper.rb
index b64dd2c19..d416d0532 100644
--- a/sentry-rails/spec/spec_helper.rb
+++ b/sentry-rails/spec/spec_helper.rb
@@ -55,7 +55,7 @@
     Sentry::Rails::Tracing.remove_active_support_notifications_patch
 
     if defined?(Sentry::Rails::ActiveJobExtensions)
-      Sentry::Rails::ActiveJobExtensions::SentryReporter.detach_retry_stopped_subscriber
+      Sentry::Rails::ActiveJobExtensions::SentryReporter.detach_handlers
     end
 
     reset_sentry_globals!

From 5ad370da7c75afb61c5a300043649c2d275114ff Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Wed, 30 Apr 2025 11:19:22 +0000
Subject: [PATCH 6/8] DRY up event handling

---
 sentry-rails/lib/sentry/rails/active_job.rb | 44 ++++++++++-----------
 sentry-rails/lib/sentry/rails/railtie.rb    |  7 +---
 sentry-rails/spec/spec_helper.rb            |  2 +-
 3 files changed, 24 insertions(+), 29 deletions(-)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index 0dcc2d930..9b41cba78 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require "set"
+
 module Sentry
   module Rails
     module ActiveJobExtensions
@@ -20,7 +22,11 @@ def already_supported_by_sentry_integration?
       class SentryReporter
         OP_NAME = "queue.active_job"
         SPAN_ORIGIN = "auto.queue.active_job"
-        NOTIFICATION_NAME = "retry_stopped.active_job"
+
+        EVENT_HANDLERS = {
+          "enqueue_retry.active_job" => :retry_handler,
+          "retry_stopped.active_job" => :retry_stopped_handler
+        }
 
         class << self
           def record(job, &block)
@@ -71,32 +77,19 @@ def capture_exception(job, e)
             )
           end
 
-          def register_retry_subscriber
-            unless @retry_subscriber
-              @retry_subscriber = ActiveSupport::Notifications.subscribe("enqueue_retry.active_job") do |*args|
-                retry_handler(*args)
-              end
-            end
-          end
-
-          def register_retry_stopped_subscriber
-            unless @retry_stopped_subscriber
-              @retry_stopped_subscriber = ActiveSupport::Notifications.subscribe(NOTIFICATION_NAME) do |*args|
-                retry_stopped_handler(*args)
+          def register_event_handlers
+            EVENT_HANDLERS.each do |name, handler|
+              subscribers << ActiveSupport::Notifications.subscribe(name) do |*args|
+                public_send(handler, *args)
               end
             end
           end
 
-          def detach_handlers
-            if @retry_stopped_subscriber
-              ActiveSupport::Notifications.unsubscribe(@retry_stopped_subscriber)
-              @retry_stopped_subscriber = nil
-            end
-
-            if @retry_handler
-              ActiveSupport::Notifications.unsubscribe(@retry_handler)
-              @retry_handler = nil
+          def detach_event_handlers
+            subscribers.each do |subscriber|
+              ActiveSupport::Notifications.unsubscribe(subscriber)
             end
+            subscribers.clear
           end
 
           def retry_handler(*args)
@@ -117,6 +110,7 @@ def retry_stopped_handler(*args)
 
             return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
             return unless Sentry.configuration.rails.active_job_report_after_job_retries
+
             capture_exception(job, error)
           end
 
@@ -156,6 +150,12 @@ def sentry_serialize_arguments(argument)
               argument
             end
           end
+
+          private
+
+          def subscribers
+            @__subscribers__ ||= Set.new
+          end
         end
       end
     end
diff --git a/sentry-rails/lib/sentry/rails/railtie.rb b/sentry-rails/lib/sentry/rails/railtie.rb
index a31ae12df..d2cf03d57 100644
--- a/sentry-rails/lib/sentry/rails/railtie.rb
+++ b/sentry-rails/lib/sentry/rails/railtie.rb
@@ -54,7 +54,7 @@ class Railtie < ::Rails::Railtie
 
       # Presence of ActiveJob is no longer a reliable cue
       if defined?(Sentry::Rails::ActiveJobExtensions)
-        register_active_job_subscribers
+        Sentry::Rails::ActiveJobExtensions::SentryReporter.register_event_handlers
       end
     end
 
@@ -142,10 +142,5 @@ def register_error_subscriber(app)
       require "sentry/rails/error_subscriber"
       app.executor.error_reporter.subscribe(Sentry::Rails::ErrorSubscriber.new)
     end
-
-    def register_active_job_subscribers
-      Sentry::Rails::ActiveJobExtensions::SentryReporter.register_retry_subscriber
-      Sentry::Rails::ActiveJobExtensions::SentryReporter.register_retry_stopped_subscriber
-    end
   end
 end
diff --git a/sentry-rails/spec/spec_helper.rb b/sentry-rails/spec/spec_helper.rb
index d416d0532..e3accdf98 100644
--- a/sentry-rails/spec/spec_helper.rb
+++ b/sentry-rails/spec/spec_helper.rb
@@ -55,7 +55,7 @@
     Sentry::Rails::Tracing.remove_active_support_notifications_patch
 
     if defined?(Sentry::Rails::ActiveJobExtensions)
-      Sentry::Rails::ActiveJobExtensions::SentryReporter.detach_handlers
+      Sentry::Rails::ActiveJobExtensions::SentryReporter.detach_event_handlers
     end
 
     reset_sentry_globals!

From b3c213bd64c0778c2eefd02703349cc6083e419e Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Wed, 30 Apr 2025 11:23:25 +0000
Subject: [PATCH 7/8] Add a common handler_error_event

---
 sentry-rails/lib/sentry/rails/active_job.rb | 27 +++++++++++----------
 1 file changed, 14 insertions(+), 13 deletions(-)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index 9b41cba78..9be504a6f 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -93,25 +93,26 @@ def detach_event_handlers
           end
 
           def retry_handler(*args)
-            event = ActiveSupport::Notifications::Event.new(*args)
-            job = event.payload[:job]
-            error = event.payload[:error]
-
-            return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
-            return if Sentry.configuration.rails.active_job_report_after_job_retries
+            handle_error_event(*args) do |job, error|
+              return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
+              return if Sentry.configuration.rails.active_job_report_after_job_retries
 
-            capture_exception(job, error)
+              capture_exception(job, error)
+            end
           end
 
           def retry_stopped_handler(*args)
-            event = ActiveSupport::Notifications::Event.new(*args)
-            job = event.payload[:job]
-            error = event.payload[:error]
+            handle_error_event(*args) do |job, error|
+              return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
+              return unless Sentry.configuration.rails.active_job_report_after_job_retries
 
-            return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
-            return unless Sentry.configuration.rails.active_job_report_after_job_retries
+              capture_exception(job, error)
+            end
+          end
 
-            capture_exception(job, error)
+          def handle_error_event(*args)
+            event = ActiveSupport::Notifications::Event.new(*args)
+            yield(event.payload[:job], event.payload[:error])
           end
 
           def finish_sentry_transaction(transaction, status)

From 2b6b7f1cc55b436a6763d0cd0e08ec74e239afd3 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Wed, 30 Apr 2025 11:29:26 +0000
Subject: [PATCH 8/8] Add some comments to explain this tricky logic

---
 sentry-rails/lib/sentry/rails/active_job.rb | 5 +++++
 1 file changed, 5 insertions(+)

diff --git a/sentry-rails/lib/sentry/rails/active_job.rb b/sentry-rails/lib/sentry/rails/active_job.rb
index 9be504a6f..9b5bc7176 100644
--- a/sentry-rails/lib/sentry/rails/active_job.rb
+++ b/sentry-rails/lib/sentry/rails/active_job.rb
@@ -92,6 +92,8 @@ def detach_event_handlers
             subscribers.clear
           end
 
+          # This handler does not capture error when `active_job_report_after_job_retries` is true
+          # because in such case only the last retry that failed will capture exception
           def retry_handler(*args)
             handle_error_event(*args) do |job, error|
               return if !Sentry.initialized? || job.already_supported_by_sentry_integration?
@@ -101,6 +103,9 @@ def retry_handler(*args)
             end
           end
 
+          # This handler does not capture error when `active_job_report_after_job_retries` is false
+          # because in such cases regular execution flow that failed will capture it in `record`
+          # method
           def retry_stopped_handler(*args)
             handle_error_event(*args) do |job, error|
               return if !Sentry.initialized? || job.already_supported_by_sentry_integration?