diff --git a/config/initializers/02_sentry.rb b/config/initializers/02_sentry.rb
index 4f1c2653..556bd635 100644
--- a/config/initializers/02_sentry.rb
+++ b/config/initializers/02_sentry.rb
@@ -10,4 +10,7 @@
 
   # Any exceptions we want to prevent sending to Sentry
   config.excluded_exceptions += ['Pender::Exception::RetryLater']
+
+  # report_after_job_retries when turned on, the SDK will only report the exception after all retries have failed.
+  config.sidekiq.report_after_job_retries = true
 end
diff --git a/config/initializers/03_sidekiq.rb b/config/initializers/03_sidekiq.rb
index 2065be72..1272fb2b 100644
--- a/config/initializers/03_sidekiq.rb
+++ b/config/initializers/03_sidekiq.rb
@@ -10,11 +10,11 @@
   Sidekiq.configure_server do |config|
     config.redis = redis_config
 
-    config.death_handlers << ->(job, ex) do
-      if ex.is_a?(Pender::Exception::RetryLater)
-        ex = Pender::Exception::RetryLimitHit.new(ex)
+    config.death_handlers << ->(job, original_exception) do
+      if original_exception.is_a?(Pender::Exception::RetryLater)
+        limit_hit_exception = Pender::Exception::RetryLimitHit.new(original_exception)
       end
-      PenderSentry.notify(ex, {job: job})
+      PenderSentry.notify(limit_hit_exception, {job: job, original_exception: original_exception.cause})
     end
   end