diff --git a/pkg/connector/client.go b/pkg/connector/client.go
index 8b4e3f27..797e3b42 100644
--- a/pkg/connector/client.go
+++ b/pkg/connector/client.go
@@ -111,6 +111,7 @@ type TelegramClient struct {
 	stopTakeoutTimer   *time.Timer
 	takeoutDialogsOnce sync.Once
 	syncChatsLock      sync.Mutex
+	isNewLogin         bool
 
 	prevReactionPoll     map[networkid.PortalKey]time.Time
 	prevReactionPollLock sync.Mutex
@@ -511,6 +512,15 @@ func (t *TelegramClient) runInBackground(ctx context.Context) {
 	log := zerolog.Ctx(ctx)
 	err := t.client.Run(ctx, func(ctx context.Context) error {
 		t.clientInitialized.Set()
+		// If takeout dialog sync is enabled, we assume it'll resume from a getTakeoutID call.
+		// If not, resume dialog sync manually here.
+		if !t.isNewLogin && !t.main.Config.Takeout.DialogSync {
+			go func() {
+				if err := t.syncChats(log.WithContext(t.clientCtx), 0, false, false); err != nil {
+					log.Err(err).Msg("Failed to resume chat sync")
+				}
+			}()
+		}
 		log.Info().Msg("Client running, starting updates")
 		err := t.updatesManager.Run(ctx, t.client.API(), t.telegramUserID, updates.AuthOptions{
 			IsBot: t.metadata.IsBot,
diff --git a/pkg/connector/login.go b/pkg/connector/login.go
index 4bee7e28..68b27a1e 100644
--- a/pkg/connector/login.go
+++ b/pkg/connector/login.go
@@ -229,8 +229,9 @@ func (bl *baseLogin) finalizeLogin(
 	if err != nil {
 		return nil, fmt.Errorf("failed to save new login: %w", err)
 	}
-	ul.Client.Connect(ul.Log.WithContext(bl.main.Bridge.BackgroundCtx))
 	client := ul.Client.(*TelegramClient)
+	client.isNewLogin = true
+	client.Connect(ul.Log.WithContext(bl.main.Bridge.BackgroundCtx))
 
 	bgCtx := ul.Log.WithContext(bl.main.Bridge.BackgroundCtx)
 	go func() {
@@ -241,6 +242,8 @@ 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 client.clientDone.IsSet() {
+			log.Warn().Msg("Client is already done after login, skipping chat sync")
 		} else if err = client.syncChats(log.WithContext(client.clientCtx), 0, true, false); err != nil {
 			log.Err(err).Msg("Failed to sync chats")
 		}
@@ -259,6 +262,8 @@ func (bl *baseLogin) finalizeLogin(
 		err := client.clientInitialized.Wait(bgCtx)
 		if err != nil {
 			log.Err(err).Msg("Failed to wait for client init to start takeout")
+		} else if client.clientDone.IsSet() {
+			log.Warn().Msg("Client is already done after login, skipping takeout")
 		} else if _, err = client.getTakeoutID(bgCtx); err != nil {
 			log.Err(err).Msg("Failed to get takeout")
 		} else if client.stopTakeoutTimer == nil {