diff --git a/activejob/lib/active_job/test_helper.rb b/activejob/lib/active_job/test_helper.rb
index fa0576669ed41b95901a04677308a0691e185f43..af62fae9b93be09864eb99c1064d8078c88a6b76 100644
--- a/activejob/lib/active_job/test_helper.rb
+++ b/activejob/lib/active_job/test_helper.rb
@@ -150,7 +150,7 @@ def assert_enqueued_with(args = {}, &_block)
         matching_job = enqueued_jobs.any? do |job|
           args.all? { |key, value| value == job[key] }
         end
-        assert matching_job
+        assert matching_job, "No enqueued job found with #{args}"
       ensure
         queue_adapter.enqueued_jobs = original_enqueued_jobs + enqueued_jobs
       end
diff --git a/activejob/test/cases/test_helper_test.rb b/activejob/test/cases/test_helper_test.rb
index eab540bb6cdea2999cbf8c386fa2461031761134..71c505a65f0d7f416a143338964086975cb0431a 100644
--- a/activejob/test/cases/test_helper_test.rb
+++ b/activejob/test/cases/test_helper_test.rb
@@ -97,11 +97,13 @@ def test_assert_enqueued_job_failure
       end
     end
 
-    assert_raise ActiveSupport::TestCase::Assertion do
+    error = assert_raise ActiveSupport::TestCase::Assertion do
       assert_enqueued_with(job: NestedJob, queue: 'low') do
         NestedJob.perform_later
       end
     end
+
+    assert_equal 'No enqueued job found with {:job=>NestedJob, :queue=>"low"}', error.message
   end
 
   def test_assert_enqueued_job_args