diff --git a/internal/tests/cluster/sequential/session_cleanup_test.go b/internal/tests/cluster/sequential/session_cleanup_test.go
index 16b0fdad99..8e5ff16e90 100644
--- a/internal/tests/cluster/sequential/session_cleanup_test.go
+++ b/internal/tests/cluster/sequential/session_cleanup_test.go
@@ -289,6 +289,7 @@ func testWorkerSessionCleanupMulti(burdenCase timeoutBurdenType) func(t *testing
 		// Worker needs some extra time to become ready, otherwise for a
 		// currently-unknown reason the next successful status update fails
 		// because it's not sent before the context times out.
+		time.Sleep(5 * time.Second)
 		wg.Add(2)
 		go func() {
 			defer wg.Done()
diff --git a/internal/tests/helper/testing_helper.go b/internal/tests/helper/testing_helper.go
index 862723fa48..6788f116e5 100644
--- a/internal/tests/helper/testing_helper.go
+++ b/internal/tests/helper/testing_helper.go
@@ -442,14 +442,21 @@ func NewTestTcpServer(t *testing.T) *TestTcpServer {
 		if err != nil {
 			return false
 		}
-		_, err = c.Write([]byte{})
+		_, err = c.Write([]byte("test"))
 		if err != nil {
 			return false
 		}
-		_, err = c.Read([]byte{})
+		buf := make([]byte, len("test"))
+		_, err = c.Read(buf)
 		if err != nil {
 			return false
 		}
+		if string(buf) != "test" {
+			return false
+		}
+		if err := c.Close(); err != nil {
+			return false
+		}
 		return true
 	}, 10*time.Second, 100*time.Millisecond)
 
@@ -463,25 +470,17 @@ func ExpectWorkers(t *testing.T, c *controller.TestController, workers ...*worke
 	// validate the controller has no reported workers
 	if len(workers) == 0 {
 		require.Eventually(t, func() bool {
-			updateTimes := c.Controller().WorkerStatusUpdateTimes()
-			workerMap := map[string]*worker.TestWorker{}
-			for _, w := range workers {
-				workerMap[w.Name()] = w
-			}
-			updateTimes.Range(func(k, v any) bool {
-				require.NotNil(t, k)
-				require.NotNil(t, v)
-				if workerMap[k.(string)] == nil {
-					// We don't remove from updateTimes currently so if we're not
-					// expecting it we'll see an out-of-date entry
-					return true
+			workers := []string{}
+			c.Controller().WorkerStatusUpdateTimes().Range(func(workerId, lastStatusTime any) bool {
+				require.NotNil(t, workerId)
+				require.NotNil(t, lastStatusTime)
+				if time.Since(lastStatusTime.(time.Time)) < DefaultSuccessfulStatusGracePeriod {
+					workers = append(workers, workerId.(string))
 				}
-				assert.WithinDuration(t, time.Now(), v.(time.Time), 30*time.Second)
-				delete(workerMap, k.(string))
 				return true
 			})
-			return len(workerMap) == 0
-		}, 30*time.Second, 250*time.Millisecond)
+			return len(workers) == 0
+		}, 2*DefaultSuccessfulStatusGracePeriod, 250*time.Millisecond)
 		return
 	}