diff --git a/lib/gitlab/sidekiq_middleware/monitor.rb b/lib/gitlab/sidekiq_middleware/monitor.rb
index 0d88fe760d3..53a6132edac 100644
--- a/lib/gitlab/sidekiq_middleware/monitor.rb
+++ b/lib/gitlab/sidekiq_middleware/monitor.rb
@@ -8,8 +8,12 @@ module Gitlab
           yield
         end
       rescue Gitlab::SidekiqMonitor::CancelledError
+        # push job to DeadSet
+        payload = ::Sidekiq.dump_json(job)
+        ::Sidekiq::DeadSet.new.kill(payload, notify_failure: false)
+
         # ignore retries
-        raise Sidekiq::JobRetry::Skip
+        raise ::Sidekiq::JobRetry::Skip
       end
     end
   end
diff --git a/spec/lib/gitlab/sidekiq_middleware/monitor_spec.rb b/spec/lib/gitlab/sidekiq_middleware/monitor_spec.rb
index 2933d26a387..7319cdc2399 100644
--- a/spec/lib/gitlab/sidekiq_middleware/monitor_spec.rb
+++ b/spec/lib/gitlab/sidekiq_middleware/monitor_spec.rb
@@ -33,9 +33,17 @@ describe Gitlab::SidekiqMiddleware::Monitor do
         end
       end
 
-      it 'does skip this job' do
+      it 'skips the job' do
         expect { subject }.to raise_error(Sidekiq::JobRetry::Skip)
       end
+
+      it 'puts job in DeadSet' do
+        ::Sidekiq::DeadSet.new.clear
+
+        expect do
+          subject rescue Sidekiq::JobRetry::Skip
+        end.to change { ::Sidekiq::DeadSet.new.size }.by(1)
+      end
     end
   end
 end