diff --git a/services/shhext/api.go b/services/shhext/api.go
index 7bac86228..64c292880 100644
--- a/services/shhext/api.go
+++ b/services/shhext/api.go
@@ -217,22 +217,24 @@ func (api *PublicAPI) RequestMessagesSync(conf RetryConfig, r MessagesRequest) (
 
 	shh := api.service.w
 	events := make(chan whisper.EnvelopeEvent, 10)
-	sub := shh.SubscribeEnvelopeEvents(events)
-	defer sub.Unsubscribe()
 	var (
 		requestID hexutil.Bytes
 		err       error
 		retries   int
 	)
 	for retries <= conf.MaxRetries {
+		sub := shh.SubscribeEnvelopeEvents(events)
 		r.Timeout = conf.BaseTimeout + conf.StepTimeout*time.Duration(retries)
+		timeout := r.Timeout
 		// FIXME this weird conversion is required because MessagesRequest expects seconds but defines time.Duration
 		r.Timeout = time.Duration(int(r.Timeout.Seconds()))
 		requestID, err = api.RequestMessages(context.Background(), r)
 		if err != nil {
+			sub.Unsubscribe()
 			return resp, err
 		}
-		mailServerResp, err := waitForExpiredOrCompleted(common.BytesToHash(requestID), events)
+		mailServerResp, err := waitForExpiredOrCompleted(common.BytesToHash(requestID), events, timeout)
+		sub.Unsubscribe()
 		if err == nil {
 			resp.Cursor = hex.EncodeToString(mailServerResp.Cursor)
 			resp.Error = mailServerResp.Error
@@ -244,9 +246,17 @@ func (api *PublicAPI) RequestMessagesSync(conf RetryConfig, r MessagesRequest) (
 	return resp, fmt.Errorf("failed to request messages after %d retries", retries)
 }
 
-func waitForExpiredOrCompleted(requestID common.Hash, events chan whisper.EnvelopeEvent) (*whisper.MailServerResponse, error) {
+func waitForExpiredOrCompleted(requestID common.Hash, events chan whisper.EnvelopeEvent, timeout time.Duration) (*whisper.MailServerResponse, error) {
+	expired := fmt.Errorf("request %x expired", requestID)
+	after := time.NewTimer(timeout)
+	defer after.Stop()
 	for {
-		ev := <-events
+		var ev whisper.EnvelopeEvent
+		select {
+		case ev = <-events:
+		case <-after.C:
+			return nil, expired
+		}
 		if ev.Hash != requestID {
 			continue
 		}
@@ -258,7 +268,7 @@ func waitForExpiredOrCompleted(requestID common.Hash, events chan whisper.Envelo
 			}
 			return nil, errors.New("invalid event data type")
 		case whisper.EventMailServerRequestExpired:
-			return nil, errors.New("request expired")
+			return nil, expired
 		}
 	}
 }
diff --git a/services/shhext/api_test.go b/services/shhext/api_test.go
index 9dd211374..bffa9deec 100644
--- a/services/shhext/api_test.go
+++ b/services/shhext/api_test.go
@@ -220,3 +220,20 @@ func TestSyncMessagesErrors(t *testing.T) {
 		})
 	}
 }
+
+func TestExpiredOrCompleted(t *testing.T) {
+	timeout := time.Millisecond
+	events := make(chan whisper.EnvelopeEvent)
+	errors := make(chan error, 1)
+	hash := common.Hash{1}
+	go func() {
+		_, err := waitForExpiredOrCompleted(hash, events, timeout)
+		errors <- err
+	}()
+	select {
+	case <-time.After(time.Second):
+		require.FailNow(t, "timed out waiting for waitForExpiredOrCompleted to complete")
+	case err := <-errors:
+		require.EqualError(t, err, fmt.Sprintf("request %x expired", hash))
+	}
+}