diff --git a/TODO.md b/TODO.md
index c1e6bb72..964ba087 100644
--- a/TODO.md
+++ b/TODO.md
@@ -57,6 +57,7 @@
   - Quote links color in room subtitles (e.g. "> http://foo.orgA)" )
 
 - UI
+  - Make theme error/etc text colors more like name colors
   - Standardize usage of punctuation
   - Way to open context menus without a right mouse button
   - `smartVerticalFlick()` gradual acceleration
diff --git a/src/python/matrix_client.py b/src/python/matrix_client.py
index abd336ed..3d0bfb2f 100644
--- a/src/python/matrix_client.py
+++ b/src/python/matrix_client.py
@@ -12,7 +12,7 @@ from typing import (
     Any, DefaultDict, Dict, NamedTuple, Optional, Set, Tuple, Type, Union,
 )
 from urllib.parse import urlparse
-from uuid import uuid4
+from uuid import UUID, uuid4
 
 import cairosvg
 from PIL import Image as PILImage
@@ -211,17 +211,28 @@ class MatrixClient(nio.AsyncClient):
 
 
     async def send_file(self, room_id: str, path: Union[Path, str]) -> None:
+        item_uuid = uuid4()
+
+        try:
+            await self._send_file(item_uuid, room_id, path)
+        except asyncio.CancelledError:
+            del self.models[Upload, room_id][item_uuid]
+
+
+    async def _send_file(
+        self, item_uuid: UUID, room_id: str, path: Union[Path, str],
+    ) -> None:
         from .media_cache import Media, Thumbnail
 
         path    = Path(path)
         size    = path.resolve().stat().st_size
         encrypt = room_id in self.encrypted_rooms
 
-        upload_item = Upload(path, total_size=size)
+        task        = asyncio.Task.current_task()
+        upload_item = Upload(item_uuid, task, path, total_size=size)
         self.models[Upload, room_id][upload_item.uuid] = upload_item
 
         try:
-            raise MatrixError(111, "Ooops!")
             url, mime, crypt_dict = await self.upload(
                 path, filename=path.name, encrypt=encrypt,
             )
@@ -229,7 +240,10 @@ class MatrixClient(nio.AsyncClient):
             upload_item.status     = UploadStatus.Error
             upload_item.error      = type(err)
             upload_item.error_args = err.args
-            return
+
+            # Wait for cancellation, see parent send_file() method
+            while True:
+                await asyncio.sleep(0.1)
 
         upload_item.status = UploadStatus.Caching
         await Media.from_existing_file(self.backend.media_cache, url, path)
diff --git a/src/python/models/items.py b/src/python/models/items.py
index 0f961bdb..23f6bdb5 100644
--- a/src/python/models/items.py
+++ b/src/python/models/items.py
@@ -1,9 +1,10 @@
+import asyncio
 import re
 from dataclasses import dataclass, field
 from datetime import datetime
 from pathlib import Path
 from typing import Any, Dict, List, Optional, Tuple, Type, Union
-from uuid import uuid4
+from uuid import UUID
 
 import lxml  # nosec
 
@@ -113,6 +114,8 @@ class UploadStatus(AutoStrEnum):
 
 @dataclass
 class Upload(ModelItem):
+    uuid:       UUID                  = field()
+    task:       asyncio.Task          = field()
     filepath:   Path                  = field()
     status:     UploadStatus          = UploadStatus.Uploading
     total_size: int                   = 0
@@ -120,7 +123,6 @@ class Upload(ModelItem):
     error:      OptionalExceptionType = type(None)
     error_args: Tuple[Any, ...]       = ()
 
-    uuid:       str = field(init=False, default_factory=lambda: str(uuid4()))
     start_date: datetime = field(init=False, default_factory=datetime.now)
 
 
diff --git a/src/qml/Chat/UploadsBar.qml b/src/qml/Chat/UploadsBar.qml
index ce0ffa99..d70ba493 100644
--- a/src/qml/Chat/UploadsBar.qml
+++ b/src/qml/Chat/UploadsBar.qml
@@ -35,7 +35,34 @@ Rectangle {
             id: delegate
             width: uploadsList.width
 
+            Behavior on height { HNumberAnimation {} }
+
+            Binding {
+                id: hideBind
+                target: delegate
+                property: "height"
+                value: 0
+                when: false
+            }
+
             HRowLayout {
+                HButton {
+                    icon.name: "cancel"
+                    icon.color: theme.colors.negativeBackground
+                    padded: false
+
+                    onClicked: {
+                        // Python might take a sec to cancel, but we want
+                        // immediate visual feedback
+                        hideBind.when = true
+                        // Python will delete this model item on cancel
+                        py.call(py.getattr(model.task, "cancel"))
+                    }
+
+                    Layout.preferredWidth: theme.baseElementsHeight
+                    Layout.preferredHeight: Layout.preferredWidth
+                }
+
                 HLabel {
                     id: statusLabel
                     elide: expand ? Text.ElideNone : Text.ElideRight
@@ -108,7 +135,8 @@ Rectangle {
                 }
 
                 TapHandler {
-                    onTapped: statusLabel.expand = ! statusLabel.expand
+                    onTapped: if (model.status !== "Error")
+                        statusLabel.expand = ! statusLabel.expand
                 }
 
                 HoverHandler { id: infoRowHover }