diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7977f6e3b..1388a7da2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,6 +13,7 @@
 - Always send envelope trace header from dynamic sampling context [#2113](https://github.com/getsentry/sentry-ruby/pull/2113)
 - Improve `TestHelper`'s setup/teardown helpers ([#2116](https://github.com/getsentry/sentry-ruby/pull/2116))
   - Fixes [#2103](https://github.com/getsentry/sentry-ruby/issues/2103)
+- Fix Sidekiq tracing headers not being overwritten in case of schedules and retries [#2118](https://github.com/getsentry/sentry-ruby/pull/2118)
 
 ## 5.11.0
 
diff --git a/sentry-sidekiq/lib/sentry/sidekiq/sentry_context_middleware.rb b/sentry-sidekiq/lib/sentry/sidekiq/sentry_context_middleware.rb
index fcb6e0ada..b6cde1ea5 100644
--- a/sentry-sidekiq/lib/sentry/sidekiq/sentry_context_middleware.rb
+++ b/sentry-sidekiq/lib/sentry/sidekiq/sentry_context_middleware.rb
@@ -59,7 +59,7 @@ def call(_worker_class, job, _queue, _redis_pool)
 
         user = Sentry.get_current_scope.user
         job["sentry_user"] = user unless user.empty?
-        job["trace_propagation_headers"] = Sentry.get_trace_propagation_headers
+        job["trace_propagation_headers"] ||= Sentry.get_trace_propagation_headers
         yield
       end
     end
diff --git a/sentry-sidekiq/spec/sentry/sidekiq/sentry_context_middleware_spec.rb b/sentry-sidekiq/spec/sentry/sidekiq/sentry_context_middleware_spec.rb
index 3a2b48de0..4a8542291 100644
--- a/sentry-sidekiq/spec/sentry/sidekiq/sentry_context_middleware_spec.rb
+++ b/sentry-sidekiq/spec/sentry/sidekiq/sentry_context_middleware_spec.rb
@@ -129,5 +129,24 @@
       expect(headers["sentry-trace"]).to eq(transaction.to_sentry_trace)
       expect(headers["baggage"]).to eq(transaction.to_baggage)
     end
+
+    # sidekiq pushes the same job to the queue again from the server for schedules and retries
+    it "keeps the same trace_propagation_headers linked to the transaction when queued multiple times" do
+      client.push('queue' => 'default', 'class' => HappyWorker, 'args' => [])
+
+      # push without span transaction to simulate pushing on the server
+      Sentry.get_current_scope.clear
+      client.push(queue.first.item)
+
+      q = queue.to_a
+      expect(q.size).to be(2)
+      first_headers = q.first["trace_propagation_headers"]
+      expect(first_headers["sentry-trace"]).to eq(transaction.to_sentry_trace)
+      expect(first_headers["baggage"]).to eq(transaction.to_baggage)
+
+      second_headers = q.second["trace_propagation_headers"]
+      expect(second_headers["sentry-trace"]).to eq(transaction.to_sentry_trace)
+      expect(second_headers["baggage"]).to eq(transaction.to_baggage)
+    end
   end
 end