diff --git a/server/src/main/java/org/opensearch/indices/replication/AbstractSegmentReplicationTarget.java b/server/src/main/java/org/opensearch/indices/replication/AbstractSegmentReplicationTarget.java
index 2275034f1ec81..5a21b10d04c06 100644
--- a/server/src/main/java/org/opensearch/indices/replication/AbstractSegmentReplicationTarget.java
+++ b/server/src/main/java/org/opensearch/indices/replication/AbstractSegmentReplicationTarget.java
@@ -162,6 +162,20 @@ public void startReplication(ActionListener<Void> listener, BiConsumer<Replicati
         getCheckpointMetadata(checkpointInfoListener);
 
         checkpointInfoListener.whenComplete(checkpointInfo -> {
+            ReplicationCheckpoint getMetadataCheckpoint = checkpointInfo.getCheckpoint();
+            if (indexShard.indexSettings().isSegRepLocalEnabled() && checkpoint.isAheadOf(getMetadataCheckpoint)) {
+                // Fixes https://github.com/opensearch-project/OpenSearch/issues/18490
+                listener.onFailure(
+                    new ReplicationFailedException(
+                        "Rejecting stale metadata checkpoint ["
+                            + getMetadataCheckpoint
+                            + "] since initial checkpoint ["
+                            + checkpoint
+                            + "] is ahead of it"
+                    )
+                );
+                return;
+            }
             updateCheckpoint(checkpointInfo.getCheckpoint(), checkpointUpdater);
             final List<StoreFileMetadata> filesToFetch = getFiles(checkpointInfo);
             state.setStage(SegmentReplicationState.Stage.GET_FILES);