diff --git a/src/Main.elm b/src/Main.elm
index f51672d..8ed3e50 100644
--- a/src/Main.elm
+++ b/src/Main.elm
@@ -86,30 +86,30 @@ update msg model = case msg of
     SendFiles rid -> (model, Select.files [ "application/*" ] <| FilesSelected rid)
     ImagesSelected rid f fs -> updateUploadSelected model rid f fs (ImageUploadComplete rid)
     FilesSelected rid f fs -> updateUploadSelected model rid f fs (FileUploadComplete rid)
-    ImageUploadComplete rid ur -> updateImageUploadComplete model rid ur
-    FileUploadComplete rid ur -> updateFileUploadComplete model rid ur
+    ImageUploadComplete rid mime ur -> updateImageUploadComplete model rid mime ur
+    FileUploadComplete rid mime ur -> updateFileUploadComplete model rid mime ur
     SendImageResponse _ -> (model, Cmd.none)
     SendFileResponse _ -> (model, Cmd.none)
 
-updateFileUploadComplete : Model -> RoomId -> (Result Http.Error String) -> (Model, Cmd Msg)
-updateFileUploadComplete m rid ur =
+updateFileUploadComplete : Model -> RoomId -> String -> (Result Http.Error String) -> (Model, Cmd Msg)
+updateFileUploadComplete m rid mime ur =
     let
         command = case ur of
-            Ok u -> sendFileMessage m.apiUrl (Maybe.withDefault "" m.token) m.transactionId rid u
+            Ok u -> sendFileMessage m.apiUrl (Maybe.withDefault "" m.token) m.transactionId rid mime u
             _ -> Cmd.none
     in
         ({ m | transactionId = m.transactionId + 1}, command)
 
-updateImageUploadComplete : Model -> RoomId -> (Result Http.Error String) -> (Model, Cmd Msg)
-updateImageUploadComplete m rid ur =
+updateImageUploadComplete : Model -> RoomId -> String -> (Result Http.Error String) -> (Model, Cmd Msg)
+updateImageUploadComplete m rid mime ur =
     let
         command = case ur of
-            Ok u -> sendImageMessage m.apiUrl (Maybe.withDefault "" m.token) m.transactionId rid u
+            Ok u -> sendImageMessage m.apiUrl (Maybe.withDefault "" m.token) m.transactionId rid mime u
             _ -> Cmd.none
     in
         ({ m | transactionId = m.transactionId + 1}, command)
 
-updateUploadSelected : Model -> RoomId -> File -> List File -> (Result Http.Error String -> Msg) -> (Model, Cmd Msg)
+updateUploadSelected : Model -> RoomId -> File -> List File -> (String -> Result Http.Error String -> Msg) -> (Model, Cmd Msg)
 updateUploadSelected m rid f fs msg =
     let
         uploadCmds = List.map (uploadMediaFile m.apiUrl (Maybe.withDefault "" m.token) msg) (f::fs)
diff --git a/src/Scylla/Http.elm b/src/Scylla/Http.elm
index cb7cd0a..e48b2bf 100644
--- a/src/Scylla/Http.elm
+++ b/src/Scylla/Http.elm
@@ -40,13 +40,13 @@ sync apiUrl token nextBatch = request
     , tracker = Nothing
     }
 
-uploadMediaFile : ApiUrl -> ApiToken -> (Result Http.Error String -> Msg) -> File -> Cmd Msg
+uploadMediaFile : ApiUrl -> ApiToken -> (String -> Result Http.Error String -> Msg) -> File -> Cmd Msg
 uploadMediaFile apiUrl token msg file = request
     { method = "POST"
     , headers = authenticatedHeaders token
     , url = Builder.crossOrigin (fullMediaUrl apiUrl) [ "upload" ] [ Builder.string "filename" (name file) ]
     , body = fileBody file
-    , expect = expectJson msg <| Json.Decode.field "content_uri" Json.Decode.string
+    , expect = expectJson (msg <| mime file) <| Json.Decode.field "content_uri" Json.Decode.string
     , timeout = Nothing
     , tracker = Nothing
     }
@@ -82,18 +82,20 @@ sendTextMessage apiUrl token transactionId room message = sendMessage apiUrl tok
     , ("body", string message)
     ]
 
-sendImageMessage : ApiUrl -> ApiToken -> Int -> RoomId -> String -> Cmd Msg
-sendImageMessage apiUrl token transactionId room message = sendMessage apiUrl token transactionId room SendImageResponse
+sendImageMessage : ApiUrl -> ApiToken -> Int -> RoomId -> String -> String -> Cmd Msg
+sendImageMessage apiUrl token transactionId room mime message = sendMessage apiUrl token transactionId room SendImageResponse
     [ ("msgtype", string "m.image")
     , ("body", string "Image")
     , ("url", string message)
+    , ("info", object [ ("mimetype", string mime) ])
     ]
 
-sendFileMessage : ApiUrl -> ApiToken -> Int -> RoomId -> String -> Cmd Msg
-sendFileMessage apiUrl token transactionId room message = sendMessage apiUrl token transactionId room SendFileResponse
+sendFileMessage : ApiUrl -> ApiToken -> Int -> RoomId -> String -> String -> Cmd Msg
+sendFileMessage apiUrl token transactionId room mime message = sendMessage apiUrl token transactionId room SendFileResponse
     [ ("msgtype", string "m.file")
     , ("body", string "File")
     , ("url", string message)
+    , ("info", object [ ("mimetype", string mime) ])
     ]
 
 login : ApiUrl -> Username -> Password -> Cmd Msg
diff --git a/src/Scylla/Model.elm b/src/Scylla/Model.elm
index 3725dfb..7ee5c30 100644
--- a/src/Scylla/Model.elm
+++ b/src/Scylla/Model.elm
@@ -57,8 +57,8 @@ type Msg =
     | SendFiles RoomId
     | ImagesSelected RoomId File (List File)
     | FilesSelected RoomId File (List File)
-    | ImageUploadComplete RoomId (Result Http.Error String)
-    | FileUploadComplete RoomId (Result Http.Error String)
+    | ImageUploadComplete RoomId String (Result Http.Error String)
+    | FileUploadComplete RoomId String (Result Http.Error String)
     | SendImageResponse (Result Http.Error ())
     | SendFileResponse (Result Http.Error ())