diff --git a/src/python/matrix_client.py b/src/python/matrix_client.py
index 8613cacf..186901e0 100644
--- a/src/python/matrix_client.py
+++ b/src/python/matrix_client.py
@@ -225,9 +225,14 @@ class MatrixClient(nio.AsyncClient):
         from .media_cache import Media, Thumbnail
 
         path    = Path(path)
-        size    = path.resolve().stat().st_size
         encrypt = room_id in self.encrypted_rooms
 
+        try:
+            size = path.resolve().stat().st_size
+        except (PermissionError, FileNotFoundError):
+            # This error will be caught again by the try block later below
+            size = 0
+
         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
@@ -236,7 +241,7 @@ class MatrixClient(nio.AsyncClient):
             url, mime, crypt_dict = await self.upload(
                 path, filename=path.name, encrypt=encrypt,
             )
-        except MatrixError as err:
+        except (MatrixError, OSError) as err:
             upload_item.status     = UploadStatus.Error
             upload_item.error      = type(err)
             upload_item.error_args = err.args
@@ -257,7 +262,7 @@ class MatrixClient(nio.AsyncClient):
             "body": path.name,
             "info": {
                 "mimetype": mime,
-                "size":     size,
+                "size":     upload_item.total_size,
             },
         }
 
diff --git a/src/python/models/items.py b/src/python/models/items.py
index 23f6bdb5..ee59f0a1 100644
--- a/src/python/models/items.py
+++ b/src/python/models/items.py
@@ -126,11 +126,6 @@ class Upload(ModelItem):
     start_date: datetime = field(init=False, default_factory=datetime.now)
 
 
-    def __post_init__(self) -> None:
-        if not self.total_size:
-            self.total_size = self.filepath.resolve().stat().st_size
-
-
     def __lt__(self, other: "Upload") -> bool:
         # Sort from newest upload to oldest.
         return self.start_date > other.start_date
diff --git a/src/qml/Chat/UploadsBar.qml b/src/qml/Chat/UploadsBar.qml
index d70ba493..b269b3a3 100644
--- a/src/qml/Chat/UploadsBar.qml
+++ b/src/qml/Chat/UploadsBar.qml
@@ -60,7 +60,7 @@ Rectangle {
                     }
 
                     Layout.preferredWidth: theme.baseElementsHeight
-                    Layout.preferredHeight: Layout.preferredWidth
+                    Layout.fillHeight: true
                 }
 
                 HLabel {
@@ -93,8 +93,20 @@ Rectangle {
                             qsTr("Too large for this server: %1")
                             .arg(fileName) :
 
+                            model.error === "IsADirectoryError" ?
+                            qsTr("Can't upload folders: %1")
+                            .arg(filePath) :
+
+                            model.error === "FileNotFoundError" ?
+                            qsTr("Non-existant file: %1")
+                            .arg(filePath) :
+
+                            model.error === "PermissionError" ?
+                            qsTr("No permission to read this file: %1")
+                            .arg(filePath) :
+
                             qsTr("Unknown error for %1: %2 - %3")
-                            .arg(fileName)
+                            .arg(filePath)
                             .arg(model.error)
                             .arg(model.error_args)
                         ) :
@@ -113,6 +125,9 @@ Rectangle {
 
                     readonly property string fileName:
                         model.filepath.split("/").slice(-1)[0]
+
+                    readonly property string filePath:
+                        model.filepath.replace(/^file:\/\//, "")
                 }
 
                 HSpacer {}