diff --git a/pinot-controller/src/main/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManager.java b/pinot-controller/src/main/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManager.java
index 99a8348a80c5..fb3d08711287 100644
--- a/pinot-controller/src/main/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManager.java
+++ b/pinot-controller/src/main/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManager.java
@@ -1556,20 +1556,10 @@ public void uploadToDeepStoreIfMissing(TableConfig tableConfig, List<SegmentZKMe
                     segmentName));
           }
 
-          ServerSegmentMetadataReader serverSegmentMetadataReader = new ServerSegmentMetadataReader();
-          Collections.shuffle(peerSegmentURIs);
-          URI uriToUpload = peerSegmentURIs.get(0);
-          for (URI uri : peerSegmentURIs) {
-            uriToUpload = uri;
-            LOGGER.info("Get CRC from server {} for LLC segment {}", uri, segmentName);
-            String crcFromServer = serverSegmentMetadataReader.getCrcForSegmentFromServer(realtimeTableName,
-                segmentName, uri.toString());
-            if (crcFromServer != null && Long.parseLong(crcFromServer) == segmentZKMetadata.getCrc()) {
-              break;
-            }
-          }
-
-          String serverUploadRequestUrl = StringUtil.join("/", uriToUpload.toString(), "upload");
+          // Randomly ask one server to upload
+          URI uri = peerSegmentURIs.get(RANDOM.nextInt(peerSegmentURIs.size()));
+          String crcFromServer = getSegmentCrcFromServer(realtimeTableName, segmentName, uri.toString());
+          String serverUploadRequestUrl = StringUtil.join("/", uri.toString(), "upload");
           serverUploadRequestUrl =
               String.format("%s?uploadTimeoutMs=%d", serverUploadRequestUrl, _deepstoreUploadRetryTimeoutMs);
           LOGGER.info("Ask server to upload LLC segment {} to deep store by this path: {}", segmentName,
@@ -1581,6 +1571,10 @@ public void uploadToDeepStoreIfMissing(TableConfig tableConfig, List<SegmentZKMe
 
           // Update segment ZK metadata by adding the download URL
           segmentZKMetadata.setDownloadUrl(segmentDownloadUrl);
+          // Update ZK crc to that of the server segment crc if unmatched
+          if (Long.parseLong(crcFromServer) != segmentZKMetadata.getCrc()) {
+            segmentZKMetadata.setCrc(Long.parseLong(crcFromServer));
+          }
           // TODO: add version check when persist segment ZK metadata
           persistSegmentZKMetadata(realtimeTableName, segmentZKMetadata, -1);
           LOGGER.info("Successfully uploaded LLC segment {} to deep store with download url: {}", segmentName,
@@ -1605,6 +1599,16 @@ public void uploadToDeepStoreIfMissing(TableConfig tableConfig, List<SegmentZKMe
     }
   }
 
+  @VisibleForTesting
+  String getSegmentCrcFromServer(String tableNameWithType, String segmentName, String endpoint) {
+    ServerSegmentMetadataReader serverSegmentMetadataReader = new ServerSegmentMetadataReader();
+    String crcFromServer = serverSegmentMetadataReader.getCrcForSegmentFromServer(tableNameWithType,
+        segmentName, endpoint);
+    Preconditions.checkState(crcFromServer != null,
+        "Failed to get CRC from endpoint %s for segment %s", endpoint, segmentName);
+    return crcFromServer;
+  }
+
   @VisibleForTesting
   boolean deepStoreUploadExecutorPendingSegmentsIsEmpty() {
     return _deepStoreUploadExecutorPendingSegments.isEmpty();
diff --git a/pinot-controller/src/test/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManagerTest.java b/pinot-controller/src/test/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManagerTest.java
index bed25bb16c12..58c393a1aa3d 100644
--- a/pinot-controller/src/test/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManagerTest.java
+++ b/pinot-controller/src/test/java/org/apache/pinot/controller/helix/core/realtime/PinotLLCRealtimeSegmentManagerTest.java
@@ -1033,6 +1033,8 @@ public void testUploadToSegmentStore()
 
     assertEquals(segmentManager.getSegmentZKMetadata(REALTIME_TABLE_NAME, segmentNames.get(0), null).getDownloadUrl(),
         expectedSegmentLocation);
+    assertEquals(segmentManager.getSegmentZKMetadata(REALTIME_TABLE_NAME, segmentNames.get(0), null).getCrc(),
+        Long.parseLong("12345678"));
     assertFalse(tempSegmentFileLocation.exists(),
         "Deep-store retry task should move the file from temp location to permanent location");
 
@@ -1196,6 +1198,11 @@ void persistSegmentZKMetadata(String realtimeTableName, SegmentZKMetadata segmen
       _segmentZKMetadataVersionMap.put(segmentName, version + 1);
     }
 
+    @Override
+    String getSegmentCrcFromServer(String tableNameWithType, String segmentName, String endpoint) {
+      return "12345678";
+    }
+
     @Override
     public IdealState getIdealState(String realtimeTableName) {
       return _idealState;