diff --git a/pkg/connector/backfill.go b/pkg/connector/backfill.go
index f7c27ea3..22e8c68f 100644
--- a/pkg/connector/backfill.go
+++ b/pkg/connector/backfill.go
@@ -110,6 +110,14 @@ func (t *TelegramClient) takeoutDialogs(ctx context.Context, takeoutID int64) er
 			return nil
 		}
 
+		if req.OffsetPeer.TypeID() == tg.InputPeerEmptyTypeID {
+			// This is the first fetch of dialogs, reset the pinned dialogs
+			// based on the list.
+			if err := t.resetPinnedDialogs(ctx, dialogs.GetDialogs()); err != nil {
+				return err
+			}
+		}
+
 		err = t.handleDialogs(ctx, dialogs, -1)
 		if err != nil {
 			return fmt.Errorf("failed to handle dialogs: %w", err)
diff --git a/pkg/connector/client.go b/pkg/connector/client.go
index 0d7bfa09..a73cf995 100644
--- a/pkg/connector/client.go
+++ b/pkg/connector/client.go
@@ -183,6 +183,9 @@ func NewTelegramClient(ctx context.Context, tc *TelegramConnector, login *bridge
 	dispatcher.OnNotifySettings(func(ctx context.Context, e tg.Entities, update *tg.UpdateNotifySettings) error {
 		return client.onNotifySettings(ctx, update)
 	})
+	dispatcher.OnPinnedDialogs(func(ctx context.Context, e tg.Entities, update *tg.UpdatePinnedDialogs) error {
+		return client.onPinnedDialogs(ctx, update)
+	})
 
 	client.ScopedStore = tc.Store.GetScopedStore(telegramUserID)
 
diff --git a/pkg/connector/config.go b/pkg/connector/config.go
index e1f9d163..6634fd2b 100644
--- a/pkg/connector/config.go
+++ b/pkg/connector/config.go
@@ -168,6 +168,8 @@ type UserLoginMetadata struct {
 
 	TakeoutDialogCrawlDone   bool               `json:"takeout_portal_crawl_done,omitempty"`
 	TakeoutDialogCrawlCursor networkid.PortalID `json:"takeout_portal_crawl_cursor,omitempty"`
+
+	PinnedDialogs []networkid.PortalID `json:"pinned_dialogs,omitempty"`
 }
 
 func (s *UserLoginSession) Load(_ context.Context) (*session.Data, error) {
diff --git a/pkg/connector/sync.go b/pkg/connector/sync.go
index 7b14face..f8238485 100644
--- a/pkg/connector/sync.go
+++ b/pkg/connector/sync.go
@@ -13,6 +13,7 @@ import (
 	"maunium.net/go/mautrix/bridgev2/database"
 	"maunium.net/go/mautrix/bridgev2/networkid"
 	"maunium.net/go/mautrix/bridgev2/simplevent"
+	"maunium.net/go/mautrix/event"
 
 	"go.mau.fi/mautrix-telegram/pkg/connector/ids"
 )
@@ -40,9 +41,24 @@ func (t *TelegramClient) SyncChats(ctx context.Context) error {
 		return err
 	}
 
+	if err := t.resetPinnedDialogs(ctx, dialogs.GetDialogs()); err != nil {
+		return err
+	}
+
 	return t.handleDialogs(ctx, dialogs, t.main.Config.Sync.CreateLimit)
 }
 
+func (t *TelegramClient) resetPinnedDialogs(ctx context.Context, dialogs []tg.DialogClass) error {
+	t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs = nil
+	for _, dialog := range dialogs {
+		if dialog.GetPinned() {
+			portalKey := t.makePortalKeyFromPeer(dialog.GetPeer())
+			t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs = append(t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs, portalKey.ID)
+		}
+	}
+	return t.userLogin.Save(ctx)
+}
+
 func (t *TelegramClient) handleDialogs(ctx context.Context, dialogs tg.ModifiedMessagesDialogs, createLimit int) error {
 	log := zerolog.Ctx(ctx)
 
@@ -106,6 +122,9 @@ func (t *TelegramClient) handleDialogs(ctx context.Context, dialogs tg.ModifiedM
 		} else {
 			userLocalInfo.MutedUntil = &bridgev2.Unmuted
 		}
+		if dialog.Pinned {
+			userLocalInfo.Tag = ptr.Ptr(event.RoomTagFavourite)
+		}
 
 		t.main.Bridge.QueueRemoteEvent(t.userLogin, &simplevent.ChatResync{
 			ChatInfo: &bridgev2.ChatInfo{Name: &portal.Name, UserLocal: &userLocalInfo},
diff --git a/pkg/connector/telegram.go b/pkg/connector/telegram.go
index 8526ef75..55f20873 100644
--- a/pkg/connector/telegram.go
+++ b/pkg/connector/telegram.go
@@ -758,6 +758,53 @@ func (t *TelegramClient) HandleMute(ctx context.Context, msg *bridgev2.MatrixMut
 	return err
 }
 
+func (t *TelegramClient) onPinnedDialogs(ctx context.Context, msg *tg.UpdatePinnedDialogs) error {
+	needsUnpinning := map[networkid.PortalKey]struct{}{}
+	for _, portalID := range t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs {
+		pt, id, err := ids.ParsePortalID(portalID)
+		if err != nil {
+			return err
+		}
+		needsUnpinning[t.makePortalKeyFromID(pt, id)] = struct{}{}
+	}
+	t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs = nil
+
+	for _, d := range msg.Order {
+		dialog, ok := d.(*tg.DialogPeer)
+		if !ok {
+			continue
+		}
+		portalKey := t.makePortalKeyFromPeer(dialog.Peer)
+		delete(needsUnpinning, portalKey)
+		t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs = append(t.userLogin.Metadata.(*UserLoginMetadata).PinnedDialogs, portalKey.ID)
+
+		t.main.Bridge.QueueRemoteEvent(t.userLogin, &simplevent.ChatResync{
+			ChatInfo: &bridgev2.ChatInfo{UserLocal: &bridgev2.UserLocalPortalInfo{
+				Tag: ptr.Ptr(event.RoomTagFavourite),
+			}},
+			EventMeta: simplevent.EventMeta{
+				Type:      bridgev2.RemoteEventChatResync,
+				PortalKey: portalKey,
+			},
+		})
+	}
+
+	var empty event.RoomTag
+	for portalKey := range needsUnpinning {
+		t.main.Bridge.QueueRemoteEvent(t.userLogin, &simplevent.ChatResync{
+			ChatInfo: &bridgev2.ChatInfo{UserLocal: &bridgev2.UserLocalPortalInfo{
+				Tag: &empty,
+			}},
+			EventMeta: simplevent.EventMeta{
+				Type:      bridgev2.RemoteEventChatResync,
+				PortalKey: portalKey,
+			},
+		})
+	}
+
+	return t.userLogin.Save(ctx)
+}
+
 func (t *TelegramClient) HandleRoomTag(ctx context.Context, msg *bridgev2.MatrixRoomTag) error {
 	inputPeer, err := t.inputPeerForPortalID(ctx, msg.Portal.ID)
 	if err != nil {