diff --git a/TODO.md b/TODO.md
index 727970bc..e3b72586 100644
--- a/TODO.md
+++ b/TODO.md
@@ -2,8 +2,8 @@
 
 ## Before release
 
-- Catch 5xx errors and retry 
-- nio ClientTimeout
+- Catch server 5xx errors when sending message and retry 
+- nio ClientTimeout (to fix sync hanging after network changes or hibernation)
 - Update docstrings
 - Update README.md
 
diff --git a/src/backend/matrix_client.py b/src/backend/matrix_client.py
index a5acdace..dc742448 100644
--- a/src/backend/matrix_client.py
+++ b/src/backend/matrix_client.py
@@ -117,6 +117,7 @@ class MatrixClient(nio.AsyncClient):
         self.load_rooms_task:    Optional[asyncio.Future] = None
 
         self.upload_monitors: Dict[UUID, nio.TransferMonitor] = {}
+        self.upload_tasks:    Dict[UUID, asyncio.Task]        = {}
 
         self.first_sync_done: asyncio.Event      = asyncio.Event()
         self.first_sync_date: Optional[datetime] = None
@@ -336,7 +337,7 @@ class MatrixClient(nio.AsyncClient):
         if isinstance(uuid, str):
             uuid = UUID(uuid)
 
-        self.upload_monitors[uuid].cancel = True
+        self.upload_tasks[uuid].cancel()
 
 
     async def send_file(self, room_id: str, path: Union[Path, str]) -> None:
@@ -349,6 +350,7 @@ class MatrixClient(nio.AsyncClient):
         except (nio.TransferCancelledError, asyncio.CancelledError):
             log.info("Deleting item for cancelled upload %s", item_uuid)
             del self.upload_monitors[item_uuid]
+            del self.upload_tasks[item_uuid]
             del self.models[room_id, "uploads"][str(item_uuid)]
 
 
@@ -373,9 +375,11 @@ class MatrixClient(nio.AsyncClient):
         monitor     = nio.TransferMonitor(size)
         upload_item = Upload(item_uuid, path, total_size=size)
 
-        self.upload_monitors[item_uuid]                 = monitor
         self.models[room_id, "uploads"][str(item_uuid)] = upload_item
 
+        self.upload_monitors[item_uuid] = monitor
+        self.upload_tasks[item_uuid]    = asyncio.current_task() # type: ignore
+
         def on_transferred(transferred: int) -> None:
             upload_item.uploaded  = transferred
 
@@ -539,6 +543,7 @@ class MatrixClient(nio.AsyncClient):
             content["filename"] = path.name
 
         del self.upload_monitors[item_uuid]
+        del self.upload_tasks[item_uuid]
         del self.models[room_id, "uploads"][str(upload_item.id)]
 
         await self._local_echo(
diff --git a/src/gui/Pages/Chat/FileTransfer/Transfer.qml b/src/gui/Pages/Chat/FileTransfer/Transfer.qml
index 4d9b2cb3..39d17b75 100644
--- a/src/gui/Pages/Chat/FileTransfer/Transfer.qml
+++ b/src/gui/Pages/Chat/FileTransfer/Transfer.qml
@@ -9,6 +9,8 @@ HColumnLayout {
     id: transfer
 
 
+    property bool cancelPending: false
+
     property int msLeft: model.time_left
     property int uploaded: model.uploaded
     readonly property int speed: model.speed
@@ -18,9 +20,7 @@ HColumnLayout {
 
 
     function cancel() {
-        // Python might take a sec to cancel, but we want
-        // immediate visual feedback
-        transfer.height = 0
+        cancelPending = true
         // Python will delete this model item on cancel
         py.callClientCoro(chat.userId, "cancel_upload", [model.id])
     }
@@ -38,8 +38,12 @@ HColumnLayout {
         HIcon {
             svgName: "uploading"
             colorize:
-                transfer.status === "Error" ? theme.colors.negativeBackground :
-                transfer.paused             ? theme.colors.middleBackground :
+                cancelPending || transfer.status === "Error" ?
+                theme.colors.negativeBackground :
+
+                transfer.paused ?
+                theme.colors.middleBackground :
+
                 theme.icons.colorize
 
             Layout.preferredWidth: theme.baseElementsHeight
@@ -51,7 +55,11 @@ HColumnLayout {
             wrapMode: expand ? Text.Wrap : Text.NoWrap
 
             text:
-                status === "Uploading" ? fileName :
+                cancelPending ?
+                qsTr("Cancelling...") :
+
+                status === "Uploading" ?
+                fileName :
 
                 status === "Caching" ?
                 qsTr("Caching %1...").arg(fileName) :
@@ -179,7 +187,7 @@ HColumnLayout {
 
         // TODO: bake this in hprogressbar
         foregroundColor:
-            status === "Error" ?
+            cancelPending || status === "Error" ?
             theme.controls.progressBar.errorForeground :
 
             transfer.paused ?