diff --git a/pkg/connector/client.go b/pkg/connector/client.go
index e65fe919..6259ac2f 100644
--- a/pkg/connector/client.go
+++ b/pkg/connector/client.go
@@ -81,7 +81,7 @@ type TelegramClient struct {
 	updatesManager    *updates.Manager
 	clientCtx         context.Context
 	clientCancel      context.CancelFunc
-	clientDone        *Future[error]
+	clientDone        *exsync.Event
 	clientInitialized *exsync.Event
 	mu                sync.Mutex
 
@@ -166,6 +166,7 @@ func NewTelegramClient(ctx context.Context, tc *TelegramConnector, login *bridge
 		prevReactionPoll: map[networkid.PortalKey]time.Time{},
 
 		clientInitialized: exsync.NewEvent(),
+		clientDone:        exsync.NewEvent(),
 	}
 
 	if !login.Metadata.(*UserLoginMetadata).Session.HasAuthKey() {
@@ -411,6 +412,9 @@ func (t *TelegramClient) sendBadCredentialsOrUnknownError(err error) {
 			StateEvent: status.StateUnknownError,
 			Error:      "tg-unknown-error",
 			Message:    humanise.Error(err),
+			Info: map[string]any{
+				"go_error": err.Error(),
+			},
 		})
 	}
 }
@@ -508,15 +512,11 @@ func (t *TelegramClient) onAuthError(err error) {
 	}()
 }
 
-func (t *TelegramClient) Connect(_ context.Context) {
+func (t *TelegramClient) Connect(ctx context.Context) {
 	t.mu.Lock()
 	defer t.mu.Unlock()
 
-	ctx := context.Background()
-
-	log := zerolog.Ctx(context.Background()).With().Int64("user_id", t.telegramUserID).Logger()
-	ctx = log.WithContext(ctx)
-
+	log := zerolog.Ctx(ctx)
 	if !t.metadata.Session.HasAuthKey() {
 		log.Warn().Msg("user does not have an auth key, sending bad credentials state")
 		t.sendBadCredentialsOrUnknownError(ErrNoAuthKey)
@@ -532,39 +532,38 @@ func (t *TelegramClient) Connect(_ context.Context) {
 	ctx, cancel := context.WithCancel(ctx)
 	t.clientCtx = ctx
 	t.clientCancel = cancel
-	t.clientDone = NewFuture[error]()
+	t.clientDone.Clear()
 	t.clientInitialized.Clear()
+	go t.runInBackground(ctx)
+}
 
-	runTelegramClient(ctx, t.client, t.clientInitialized, t.clientDone, func(ctx context.Context) error {
+func (t *TelegramClient) runInBackground(ctx context.Context) {
+	log := zerolog.Ctx(ctx)
+	err := t.client.Run(ctx, func(ctx context.Context) error {
+		t.clientInitialized.Set()
 		log.Info().Msg("Client running starting updates")
 		return t.updatesManager.Run(ctx, t.client.API(), t.telegramUserID, updates.AuthOptions{
 			IsBot: t.metadata.IsBot,
 		})
 	})
-}
-
-func runTelegramClient(ctx context.Context, client *telegram.Client, initialized *exsync.Event, done *Future[error], callback func(ctx context.Context) error) {
-	go func() {
-		err := client.Run(ctx, func(ctx context.Context) error {
-			initialized.Set()
-			return callback(ctx)
-		})
-		initialized.Set()
-		done.Set(err)
-	}()
+	t.clientDone.Set()
+	t.clientInitialized.Set()
+	if err != nil {
+		log.Err(err).Msg("Client exited with error")
+		t.sendBadCredentialsOrUnknownError(err)
+	}
 }
 
 func (t *TelegramClient) Disconnect() {
 	t.mu.Lock()
 	defer t.mu.Unlock()
 
-	t.userLogin.Log.Info().Msg("Disconnecting client")
+	t.userLogin.Log.Debug().Msg("Disconnecting client")
 
 	if t.clientCancel != nil {
 		t.clientCancel()
-		t.userLogin.Log.Info().Msg("Waiting for client")
-		err, _ := t.clientDone.Get(context.Background())
-		t.userLogin.Log.Info().Err(err).Msg("Client done")
+		t.userLogin.Log.Debug().Msg("Waiting for client disconnection")
+		<-t.clientDone.GetChan()
 	}
 
 	t.userLogin.Log.Info().Msg("Disconnect complete")
@@ -614,7 +613,8 @@ func (t *TelegramClient) getSingleChannel(ctx context.Context, id int64) (*tg.Ch
 
 func (t *TelegramClient) IsLoggedIn() bool {
 	// TODO use less hacky check than context cancellation
-	return t != nil && t.clientCtx != nil && t.client != nil && t.clientCtx.Err() == nil &&
+	return t != nil && t.client != nil &&
+		t.clientInitialized.IsSet() && !t.clientDone.IsSet() &&
 		t.metadata.Session.HasAuthKey()
 }
 
diff --git a/pkg/connector/login.go b/pkg/connector/login.go
index 9cf116ba..e157e5a2 100644
--- a/pkg/connector/login.go
+++ b/pkg/connector/login.go
@@ -17,6 +17,7 @@
 package connector
 
 import (
+	"cmp"
 	"context"
 	"errors"
 	"fmt"
@@ -25,7 +26,6 @@ import (
 	"time"
 
 	"github.com/rs/zerolog"
-	"go.mau.fi/util/exsync"
 	"go.mau.fi/zerozap"
 	"go.uber.org/zap"
 	"maunium.net/go/mautrix/bridgev2"
@@ -136,13 +136,22 @@ func (bl *baseLogin) makeClient(ctx context.Context, dispatcher *tg.UpdateDispat
 	})
 
 	bl.ctx, bl.cancel = context.WithTimeoutCause(log.WithContext(bl.main.Bridge.BackgroundCtx), LoginTimeout, ErrLoginTimeout)
-	initialized := exsync.NewEvent()
-	done := NewFuture[error]()
-	runTelegramClient(bl.ctx, bl.client, initialized, done, waitContextDone)
+	connectResult := NewFuture[error]()
+	go func() {
+		err := bl.client.Run(bl.ctx, func(ctx context.Context) error {
+			connectResult.Set(nil)
+			<-ctx.Done()
+			return ctx.Err()
+		})
+		connectResult.Set(err)
+		if err != nil && !errors.Is(err, bl.ctx.Err()) {
+			log.Err(err).Msg("Login client exited with error")
+		}
+	}()
 
 	log.Debug().Msg("Waiting for client to connect")
-	err := initialized.Wait(ctx)
-	if err != nil {
+	connErr, ctxErr := connectResult.Get(ctx)
+	if err := cmp.Or(connErr, ctxErr); err != nil {
 		bl.Cancel()
 		return err
 	}
diff --git a/pkg/gotd/telegram/connect.go b/pkg/gotd/telegram/connect.go
index e5d114e2..db7e2fd1 100644
--- a/pkg/gotd/telegram/connect.go
+++ b/pkg/gotd/telegram/connect.go
@@ -139,8 +139,8 @@ func (c *Client) Run(ctx context.Context, f func(ctx context.Context) error) (er
 	// handling or pool creation.
 	c.ctx, c.cancel = context.WithCancel(ctx)
 
-	c.log.Info("Starting")
-	defer c.log.Info("Closed")
+	c.log.Info("Client starting")
+	defer c.log.Info("Client closed")
 	// Cancel client on exit.
 	defer c.cancel()
 	defer func() {