diff --git a/CHANGELOG.md b/CHANGELOG.md
index debf9e9e..b7b23997 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,7 +6,8 @@
 - Improve: Backup screen clearer and easier to understand
 - Improve: Show username above messages in group chats
 - Fix: Background audio correctly pauses and resumes when viewing videos
-- Fix: Multiple bug fixes
+- Fix: Sometimes old messages were being received as duplicates
+- Fix: Multiple smaller bug fixes
 
 ## 0.5.0
 
diff --git a/lib/src/database/daos/receipts.dao.dart b/lib/src/database/daos/receipts.dao.dart
index f79a2281..d15b85e0 100644
--- a/lib/src/database/daos/receipts.dao.dart
+++ b/lib/src/database/daos/receipts.dao.dart
@@ -72,7 +72,7 @@ class ReceiptsDao extends DatabaseAccessor<TwonlyDB> with _$ReceiptsDaoMixin {
     await (delete(receivedReceipts)..where(
           (t) => (t.createdAt.isSmallerThanValue(
             clock.now().subtract(
-              const Duration(days: 25),
+              const Duration(days: 45),
             ),
           )),
         ))
diff --git a/lib/src/services/api/messages.api.dart b/lib/src/services/api/messages.api.dart
index c46a4c36..9c2aa47d 100644
--- a/lib/src/services/api/messages.api.dart
+++ b/lib/src/services/api/messages.api.dart
@@ -114,22 +114,6 @@ Future<(Uint8List, Uint8List?)?> _tryToSendCompleteMessageInternal({
     // ignore: parameter_assignments
     receipt = loadedReceipt;
 
-    if (receipt.retryCount >= 2) {
-      // After two retries, change the receiptId. This addresses a bug where the receiver received the message and marked it as received,
-      // but the app was closed before the message was fully processed. Because the receipt was already stored, subsequent retries were
-      // detected as duplicates and rejected.
-      final oldReceiptId = receipt.receiptId;
-      final updatedReceipt = await twonlyDB.receiptsDao.rotateReceiptId(
-        oldReceiptId,
-      );
-      if (updatedReceipt != null) {
-        Log.info(
-          'Changed receiptId $oldReceiptId to ${updatedReceipt.receiptId} as retryCount is ${receipt.retryCount}',
-        );
-        receipt = updatedReceipt;
-      }
-    }
-
     final contact = await twonlyDB.contactsDao.getContactById(
       receipt.contactId,
     );
diff --git a/lib/src/services/api/server_messages.api.dart b/lib/src/services/api/server_messages.api.dart
index 77498eb5..cd778309 100644
--- a/lib/src/services/api/server_messages.api.dart
+++ b/lib/src/services/api/server_messages.api.dart
@@ -141,6 +141,26 @@ Future<void> _handleClient2ClientMessage(
   }
 
   if (await twonlyDB.receiptsDao.isDuplicated(receiptId)) {
+    Log.info(
+      '[$receiptId] Message is a duplicate. Sending delivery receipt again.',
+    );
+    try {
+      final response = Message(type: Message_Type.SENDER_DELIVERY_RECEIPT);
+      await twonlyDB.receiptsDao.insertReceipt(
+        ReceiptsCompanion(
+          receiptId: Value(receiptId),
+          contactId: Value(fromUserId),
+          message: Value(response.writeToBuffer()),
+          contactWillSendsReceipt: const Value(false),
+        ),
+      );
+      await tryToSendCompleteMessage(
+        receiptId: receiptId,
+        blocking: false,
+      );
+    } catch (e) {
+      Log.warn('[$receiptId] Error handling duplicate receipt ACK: $e');
+    }
     return;
   }