diff --git a/pkg/connector/backfill.go b/pkg/connector/backfill.go
index 608acca5..a0b8fc06 100644
--- a/pkg/connector/backfill.go
+++ b/pkg/connector/backfill.go
@@ -51,7 +51,7 @@ func (t *TelegramClient) getTakeoutID(ctx context.Context) (takeoutID int64, err
 		// Resume fetching dialogs using takeout and enqueueing them for
 		// backfill.
 		go t.takeoutDialogsOnce.Do(func() {
-			if err = t.syncChats(ctx, takeoutID, false); err != nil {
+			if err = t.syncChats(ctx, takeoutID, false, false); err != nil {
 				log.Err(err).Msg("Failed to takeout dialogs")
 			}
 		})
@@ -84,7 +84,7 @@ func (t *TelegramClient) getTakeoutID(ctx context.Context) (takeoutID int64, err
 
 		// Fetch all dialogs using takeout and enqueue them for backfill.
 		go t.takeoutDialogsOnce.Do(func() {
-			if err = t.syncChats(ctx, takeoutID, false); err != nil {
+			if err = t.syncChats(ctx, takeoutID, false, false); err != nil {
 				log.Err(err).Msg("Failed to takeout dialogs")
 			}
 		})
diff --git a/pkg/connector/chatsync.go b/pkg/connector/chatsync.go
index 42e87674..3752f163 100644
--- a/pkg/connector/chatsync.go
+++ b/pkg/connector/chatsync.go
@@ -33,7 +33,7 @@ import (
 	"go.mau.fi/mautrix-telegram/pkg/gotd/tgerr"
 )
 
-func (t *TelegramClient) syncChats(ctx context.Context, takeoutID int64, onLogin bool) error {
+func (t *TelegramClient) syncChats(ctx context.Context, takeoutID int64, onLogin, restart bool) error {
 	if takeoutID != 0 && !t.main.Config.Takeout.DialogSync {
 		return nil
 	}
@@ -53,7 +53,11 @@ func (t *TelegramClient) syncChats(ctx context.Context, takeoutID int64, onLogin
 	}
 	defer t.syncChatsLock.Unlock()
 
-	if t.metadata.DialogSyncComplete {
+	if restart {
+		t.metadata.DialogSyncCount = 0
+		t.metadata.DialogSyncComplete = false
+		t.metadata.DialogSyncCursor = ""
+	} else if t.metadata.DialogSyncComplete {
 		log.Debug().Msg("Dialogs already synced")
 		return nil
 	}
diff --git a/pkg/connector/commands.go b/pkg/connector/commands.go
index 0cbb9fec..685a06ef 100644
--- a/pkg/connector/commands.go
+++ b/pkg/connector/commands.go
@@ -54,7 +54,7 @@ func fnSync(ce *commands.Event) {
 			wg.Add(1)
 			go func() {
 				defer wg.Done()
-				if err := client.syncChats(ce.Ctx, 0, false); err != nil {
+				if err := client.syncChats(ce.Ctx, 0, false, true); err != nil {
 					ce.Reply("Failed to synchronize chats for %s: %v", login.ID, err)
 				}
 			}()
diff --git a/pkg/connector/login.go b/pkg/connector/login.go
index 7495a3b9..4bee7e28 100644
--- a/pkg/connector/login.go
+++ b/pkg/connector/login.go
@@ -241,7 +241,7 @@ func (bl *baseLogin) finalizeLogin(
 		err := client.clientInitialized.Wait(bgCtx)
 		if err != nil {
 			log.Err(err).Msg("Failed to wait for client init to sync chats after login")
-		} else if err = client.syncChats(log.WithContext(client.clientCtx), 0, true); err != nil {
+		} else if err = client.syncChats(log.WithContext(client.clientCtx), 0, true, false); err != nil {
 			log.Err(err).Msg("Failed to sync chats")
 		}
 	}()