diff --git a/managed-ledger/src/main/java/org/apache/bookkeeper/mledger/impl/ManagedCursorImpl.java b/managed-ledger/src/main/java/org/apache/bookkeeper/mledger/impl/ManagedCursorImpl.java
index f4f695714d5c2..a5cabe2cde3b2 100644
--- a/managed-ledger/src/main/java/org/apache/bookkeeper/mledger/impl/ManagedCursorImpl.java
+++ b/managed-ledger/src/main/java/org/apache/bookkeeper/mledger/impl/ManagedCursorImpl.java
@@ -1742,7 +1742,7 @@ public void asyncMarkDelete(final Position position, Map<String, Long> propertie
         // Apply rate limiting to mark-delete operations
         if (markDeleteLimiter != null && !markDeleteLimiter.tryAcquire()) {
             isDirty = true;
-            lastMarkDeleteEntry = new MarkDeleteEntry(newPosition, properties, null, null);
+            updateLastMarkDeleteEntryToLatest(newPosition, properties);
             callback.markDeleteComplete(ctx);
             return;
         }
@@ -1796,7 +1796,14 @@ void internalMarkDelete(final MarkDeleteEntry mdEntry) {
         // ledger is postponed to when the counter goes to 0.
         PENDING_MARK_DELETED_SUBMITTED_COUNT_UPDATER.incrementAndGet(this);
 
-        lastMarkDeleteEntry = mdEntry;
+        LAST_MARK_DELETE_ENTRY_UPDATER.updateAndGet(this, last -> {
+            if (last != null && last.newPosition.compareTo(mdEntry.newPosition) > 0) {
+                // keep the current value since it's later then the mdEntry.newPosition
+                return last;
+            } else {
+                return mdEntry;
+            }
+        });
 
         persistPositionToLedger(cursorLedger, mdEntry, new VoidCallback() {
             @Override
@@ -2063,9 +2070,7 @@ public void asyncDelete(Iterable<Position> positions, AsyncCallbacks.DeleteCallb
         // Apply rate limiting to mark-delete operations
         if (markDeleteLimiter != null && !markDeleteLimiter.tryAcquire()) {
             isDirty = true;
-            PositionImpl finalNewMarkDeletePosition = newMarkDeletePosition;
-            LAST_MARK_DELETE_ENTRY_UPDATER.updateAndGet(this,
-                    last -> new MarkDeleteEntry(finalNewMarkDeletePosition, last.properties, null, null));
+            updateLastMarkDeleteEntryToLatest(newMarkDeletePosition, null);
             callback.deleteComplete(ctx);
             return;
         }
@@ -2097,6 +2102,22 @@ public void markDeleteFailed(ManagedLedgerException exception, Object ctx) {
         }
     }
 
+    // update lastMarkDeleteEntry field if newPosition is later than the current lastMarkDeleteEntry.newPosition
+    private void updateLastMarkDeleteEntryToLatest(final PositionImpl newPosition,
+                                                   final Map<String, Long> properties) {
+        LAST_MARK_DELETE_ENTRY_UPDATER.updateAndGet(this, last -> {
+            if (last != null && last.newPosition.compareTo(newPosition) > 0) {
+                // keep current value, don't update
+                return last;
+            } else {
+                // use given properties or when missing, use the properties from the previous field value
+                Map<String, Long> propertiesToUse =
+                        properties != null ? properties : (last != null ? last.properties : Collections.emptyMap());
+                return new MarkDeleteEntry(newPosition, propertiesToUse, null, null);
+            }
+        });
+    }
+
     /**
      * Given a list of entries, filter out the entries that have already been individually deleted.
      *