diff --git a/lib/database/database.dart b/lib/database/database.dart
index 15ad7e7e2f..0f80948cec 100644
--- a/lib/database/database.dart
+++ b/lib/database/database.dart
@@ -86,6 +86,57 @@ class Database {
       Logger.error("Failed to perform database migrations!", error: e, trace: s);
     }
 
+    try {
+      if (ss.prefs.getBool('cloudReactionRepair-1') != true) {
+        // Repair reactions restored from iCloud that kept Apple's "p:<part>/<guid>"
+        // prefix in associatedMessageGuid — locally reactions link by the bare guid
+        final query = Database.messages.query(Message_.associatedMessageGuid.contains("/")).build();
+        final broken = query.find();
+        query.close();
+        for (Message m in broken) {
+          final amg = m.associatedMessageGuid!;
+          final prefix = amg.substring(0, amg.indexOf("/"));
+          m.associatedMessageGuid = amg.substring(amg.indexOf("/") + 1);
+          if (prefix.startsWith("p:")) {
+            m.associatedMessagePart ??= int.tryParse(prefix.substring(2));
+          }
+        }
+        if (broken.isNotEmpty) Database.messages.putMany(broken);
+        // Cloud restore used to drop messages whose chat hadn't synced yet while still
+        // advancing the checkpoint; reset the checkpoints so the next sync re-pages
+        // from the start and picks those messages up
+        await ss.prefs.remove("chatSyncToken");
+        await ss.prefs.remove("attachmentSyncToken");
+        await ss.prefs.remove("messageSyncToken");
+        await ss.prefs.setBool('cloudReactionRepair-1', true);
+        Logger.info("Repaired ${broken.length} cloud-restored reactions and reset cloud sync checkpoints");
+      }
+    } catch (e, s) {
+      Logger.error("Failed to repair cloud-restored reactions!", error: e, trace: s);
+    }
+
+    try {
+      if (ss.prefs.getBool('cloudChatIdentifierRepair-1') != true) {
+        // Live-created chats never set chatIdentifier, which cloud sync uses to route
+        // DM messages — backfill it so the next sync can attach orphaned messages
+        final allChats = Database.chats.getAll();
+        final List<Chat> repaired = [];
+        for (Chat c in allChats) {
+          if (c.chatIdentifier == null && c.handles.length == 1) {
+            c.chatIdentifier = c.handles.first.address;
+            repaired.add(c);
+          }
+        }
+        if (repaired.isNotEmpty) Database.chats.putMany(repaired);
+        // re-page messages so previously-orphaned ones get attached
+        await ss.prefs.remove("messageSyncToken");
+        await ss.prefs.setBool('cloudChatIdentifierRepair-1', true);
+        Logger.info("Backfilled chatIdentifier on ${repaired.length} chats and reset the message sync checkpoint");
+      }
+    } catch (e, s) {
+      Logger.error("Failed to backfill chat identifiers!", error: e, trace: s);
+    }
+
     initComplete.complete();
   }
 
diff --git a/lib/database/io/message.dart b/lib/database/io/message.dart
index 4440c2ef6a..077cf826bf 100644
--- a/lib/database/io/message.dart
+++ b/lib/database/io/message.dart
@@ -1112,7 +1112,35 @@ class Message {
       chat ??= Chat.findByRustGuid(c.chatId);
     }
 
-    if (chat?.isRpSms ?? true) return;
+    final chatIdParts = c.chatId.split(";");
+    if (chat == null && chatIdParts.length >= 3) {
+      // older chats may lack chatIdentifier, so fall back to matching a DM by participant address
+      final ident = chatIdParts[2];
+      if (ident.isNotEmpty && ident != "null") {
+        final query = (Database.chats.query(Chat_.dateDeleted.isNull())
+              ..linkMany(Chat_.handles, Handle_.address.equals(ident)))
+            .build();
+        final results = query.find();
+        query.close();
+        chat = results.firstWhereOrNull((ch) => !ch.isGroup);
+      }
+    }
+    if (chat == null) {
+      // last resort: route by the original chat guid carried in proto4
+      try {
+        if (c.msgProto4 != null) {
+          final proto4 = api.decodeMessageproto4(wrapped: c.msgProto4!);
+          if (proto4.groupId != null) {
+            chat = Chat.findByRustGuid(proto4.groupId!);
+          }
+        }
+      } catch (_) {}
+    }
+    if (chat == null) {
+      Logger.warn("Cloud message ${c.guid} references unknown chat ${c.chatId}; skipping");
+      return;
+    }
+    if (chat.isRpSms) return;
 
     Logger.info("Syncing new message");
 
@@ -1164,8 +1192,19 @@ class Message {
         associatedMessageType = "-${ReactionTypes.toList()[proto1.associatedMessageType! - 3000]}";
       }
     }
-    associatedMessageGuid = proto1.associatedMessageGuid;
-    associatedMessagePart = attributedBody.firstOrNull?.runs.firstWhereOrNull((b) => b.range[0] == proto1.associatedMessageRangeLocation && b.range[1] == proto1.associatedMessageRangeLength)?.attributes?.messagePart;
+    // the cloud stores the target in Apple's prefixed form ("p:<part>/<guid>"),
+    // but locally reactions are linked by the bare guid
+    var amg = proto1.associatedMessageGuid;
+    int? amgPart;
+    if (amg != null && amg.contains("/")) {
+      var prefix = amg.substring(0, amg.indexOf("/"));
+      amg = amg.substring(amg.indexOf("/") + 1);
+      if (prefix.startsWith("p:")) {
+        amgPart = int.tryParse(prefix.substring(2));
+      }
+    }
+    associatedMessageGuid = amg;
+    associatedMessagePart = amgPart ?? attributedBody.firstOrNull?.runs.firstWhereOrNull((b) => b.range[0] == proto1.associatedMessageRangeLocation && b.range[1] == proto1.associatedMessageRangeLength)?.attributes?.messagePart;
     guid = c.guid;
     var bits = c.flags.bits();
     isFromMe = (bits & IS_FROM_ME) != 0;
diff --git a/lib/services/rustpush/rustpush_service.dart b/lib/services/rustpush/rustpush_service.dart
index 6deb3c1e42..ffea7fbb4d 100644
--- a/lib/services/rustpush/rustpush_service.dart
+++ b/lib/services/rustpush/rustpush_service.dart
@@ -432,6 +432,8 @@ class RustPushBackend implements BackendService {
     var formattedHandles = addresses.map((e) => RustPushBBUtils.rustHandleToBB(e)).toList();
     var chat = Chat(
       guid: existingGuid ?? uuid.v4(),
+      // cloud sync routes DM messages by chatIdentifier; leaving it null orphans them
+      chatIdentifier: formattedHandles.length == 1 ? formattedHandles[0].address : null,
       participants: formattedHandles,
       usingHandle: handle,
       isRpSms: service == "SMS",