diff --git a/google-cloud-bigquerystorage/src/main/java/com/google/cloud/bigquery/storage/v1/ConnectionWorker.java b/google-cloud-bigquerystorage/src/main/java/com/google/cloud/bigquery/storage/v1/ConnectionWorker.java
index 67b4bc7dc5..e295320153 100644
--- a/google-cloud-bigquerystorage/src/main/java/com/google/cloud/bigquery/storage/v1/ConnectionWorker.java
+++ b/google-cloud-bigquerystorage/src/main/java/com/google/cloud/bigquery/storage/v1/ConnectionWorker.java
@@ -699,7 +699,10 @@ private void appendLoop() {
         hasMessageInWaitingQueue.await(100, TimeUnit.MILLISECONDS);
         // Check whether we should error out the current append loop.
         if (inflightRequestQueue.size() > 0) {
-          throwIfWaitCallbackTooLong(inflightRequestQueue.getFirst().requestCreationTimeStamp);
+          Instant sendInstant = inflightRequestQueue.getFirst().requestSendTimeStamp;
+          if (sendInstant != null) {
+            throwIfWaitCallbackTooLong(sendInstant);
+          }
         }
 
         // Copy the streamConnectionIsConnected guarded by lock to a local variable.
@@ -711,7 +714,9 @@ private void appendLoop() {
           // from inflightRequestQueue and prepent them onto the waitinRequestQueue. They need to be
           // prepended as they need to be sent before new requests.
           while (!inflightRequestQueue.isEmpty()) {
-            waitingRequestQueue.addFirst(inflightRequestQueue.pollLast());
+            AppendRequestAndResponse requestWrapper = inflightRequestQueue.pollLast();
+            requestWrapper.requestSendTimeStamp = null;
+            waitingRequestQueue.addFirst(requestWrapper);
           }
 
           // If any of the inflight messages were meant to be ignored during requestCallback, they
@@ -721,7 +726,6 @@ private void appendLoop() {
         while (!this.waitingRequestQueue.isEmpty()) {
           AppendRequestAndResponse requestWrapper = this.waitingRequestQueue.pollFirst();
           waitForBackoffIfNecessary(requestWrapper);
-          requestWrapper.trySetRequestInsertQueueTime();
           this.inflightRequestQueue.add(requestWrapper);
           localQueue.addLast(requestWrapper);
         }
@@ -760,6 +764,7 @@ private void appendLoop() {
         firstRequestForTableOrSchemaSwitch = true;
       }
       while (!localQueue.isEmpty()) {
+        localQueue.peekFirst().setRequestSendQueueTime();
         AppendRowsRequest originalRequest = localQueue.pollFirst().message;
         AppendRowsRequest.Builder originalRequestBuilder = originalRequest.toBuilder();
         // Always respect the first writer schema seen by the loop.
@@ -1217,6 +1222,7 @@ private void doneCallback(Throwable finalStatus) {
   private AppendRequestAndResponse pollInflightRequestQueue(boolean pollLast) {
     AppendRequestAndResponse requestWrapper =
         pollLast ? inflightRequestQueue.pollLast() : inflightRequestQueue.poll();
+    requestWrapper.requestSendTimeStamp = null;
     --this.inflightRequests;
     this.inflightBytes -= requestWrapper.messageSize;
     this.inflightReduced.signal();
@@ -1256,7 +1262,9 @@ static final class AppendRequestAndResponse {
 
     TimedAttemptSettings attemptSettings;
 
-    Instant requestCreationTimeStamp;
+    // Time at which request was last sent over the network.
+    // If a response is no longer expected this is set back to null.
+    Instant requestSendTimeStamp;
 
     AppendRequestAndResponse(
         AppendRowsRequest message, StreamWriter streamWriter, RetrySettings retrySettings) {
@@ -1276,11 +1284,8 @@ static final class AppendRequestAndResponse {
       }
     }
 
-    void trySetRequestInsertQueueTime() {
-      // Only set the first time the caller tries to set the timestamp.
-      if (requestCreationTimeStamp == null) {
-        requestCreationTimeStamp = Instant.now();
-      }
+    void setRequestSendQueueTime() {
+      requestSendTimeStamp = Instant.now();
     }
   }
 
diff --git a/google-cloud-bigquerystorage/src/test/java/com/google/cloud/bigquery/storage/v1/StreamWriterTest.java b/google-cloud-bigquerystorage/src/test/java/com/google/cloud/bigquery/storage/v1/StreamWriterTest.java
index 2ded205822..06a558e658 100644
--- a/google-cloud-bigquerystorage/src/test/java/com/google/cloud/bigquery/storage/v1/StreamWriterTest.java
+++ b/google-cloud-bigquerystorage/src/test/java/com/google/cloud/bigquery/storage/v1/StreamWriterTest.java
@@ -1809,6 +1809,33 @@ public void testAppendSuccessAndInternalQuotaErrorRetrySuccess() throws Exceptio
     writer.close();
   }
 
+  @Test
+  public void testInternalQuotaError_MaxWaitTimeExceed_RetrySuccess() throws Exception {
+    // In order for the test to succeed, the given request must complete successfully even after all
+    // the retries. The fake server is configured to fail 3 times with a quota error. This means the
+    // client will perform retry with exponential backoff. The fake server injects 1 second of delay
+    // for each response. In addition, the exponential backoff injects a couple of seconds of delay.
+    // This yields an overall delay of about 5 seconds before the request succeeds. If the request
+    // send timestamp was being set only once, this would eventually exceed the 4 second timeout
+    // limit, and throw an exception. With the current behavior, the request send timestamp is reset
+    // each time a retry is performed, so we never exceed the 4 second timeout limit.
+    StreamWriter.setMaxRequestCallbackWaitTime(java.time.Duration.ofSeconds(4));
+    testBigQueryWrite.setResponseSleep(Duration.ofSeconds(1));
+    StreamWriter writer = getTestStreamWriterRetryEnabled();
+    testBigQueryWrite.addStatusException(
+        com.google.rpc.Status.newBuilder().setCode(Code.RESOURCE_EXHAUSTED.ordinal()).build());
+    testBigQueryWrite.addStatusException(
+        com.google.rpc.Status.newBuilder().setCode(Code.RESOURCE_EXHAUSTED.ordinal()).build());
+    testBigQueryWrite.addStatusException(
+        com.google.rpc.Status.newBuilder().setCode(Code.RESOURCE_EXHAUSTED.ordinal()).build());
+    testBigQueryWrite.addResponse(createAppendResponse(0));
+
+    ApiFuture<AppendRowsResponse> appendFuture1 =
+        writer.append(createProtoRows(new String[] {"A"}));
+    assertEquals(0, appendFuture1.get().getAppendResult().getOffset().getValue());
+    writer.close();
+  }
+
   @Test
   public void testAppendSuccessAndInternalErrorRetrySuccessExclusive() throws Exception {
     // Ensure we return an error from the fake server when a retry is in progress