diff --git a/resources/icons/ui/image.svg b/resources/icons/ui/image.svg
new file mode 100644
index 0000000000000000000000000000000000000000..ca73a76e2c2b6e6d27d5b9f512ec514220a505e5
--- /dev/null
+++ b/resources/icons/ui/image.svg
@@ -0,0 +1 @@
+<svg width="512" height="512" fill="none" viewBox="0 0 24 24" xmlns="http://www.w3.org/2000/svg"><path d="M17.75 3A3.25 3.25 0 0 1 21 6.25v11.5A3.25 3.25 0 0 1 17.75 21H6.25A3.25 3.25 0 0 1 3 17.75V6.25A3.25 3.25 0 0 1 6.25 3h11.5Zm.58 16.401-5.805-5.686a.75.75 0 0 0-.966-.071l-.084.07-5.807 5.687c.182.064.378.099.582.099h11.5c.203 0 .399-.035.58-.099l-5.805-5.686L18.33 19.4ZM17.75 4.5H6.25A1.75 1.75 0 0 0 4.5 6.25v11.5c0 .208.036.408.103.594l5.823-5.701a2.25 2.25 0 0 1 3.02-.116l.128.116 5.822 5.702c.067-.186.104-.386.104-.595V6.25a1.75 1.75 0 0 0-1.75-1.75Zm-2.498 2a2.252 2.252 0 1 1 0 4.504 2.252 2.252 0 0 1 0-4.504Zm0 1.5a.752.752 0 1 0 0 1.504.752.752 0 0 0 0-1.504Z" fill="#212121"/></svg>
diff --git a/resources/icons/ui/music.svg b/resources/icons/ui/music.svg
new file mode 100644
index 0000000000000000000000000000000000000000..5f72b73685ff1e05b8d80ae9b4aa6137e918764d
--- /dev/null
+++ b/resources/icons/ui/music.svg
@@ -0,0 +1 @@
+<svg width="512" height="512" fill="none" viewBox="0 0 24 24" xmlns="http://www.w3.org/2000/svg"><path d="M19.698 2.148A.75.75 0 0 1 20 2.75v13.5a.764.764 0 0 1-.004.079 3.5 3.5 0 1 1-1.496-2.702V7.758l-8.5 2.55v7.942a.756.756 0 0 1-.004.079A3.5 3.5 0 1 1 8.5 15.627V5.75a.75.75 0 0 1 .534-.718l10-3a.75.75 0 0 1 .664.116ZM10 8.742l8.5-2.55V3.758L10 6.308v2.434ZM6.5 16.5a2 2 0 1 0 0 4 2 2 0 0 0 0-4Zm8 0a2 2 0 1 0 4 0 2 2 0 0 0-4 0Z" fill="#212121"/></svg>
diff --git a/resources/icons/ui/video-file.svg b/resources/icons/ui/video-file.svg
new file mode 100644
index 0000000000000000000000000000000000000000..08c0a6bb26432d925d56dc38b9290ac4561facfd
--- /dev/null
+++ b/resources/icons/ui/video-file.svg
@@ -0,0 +1 @@
+<svg width="512" height="512" fill="none" viewBox="0 0 24 24" xmlns="http://www.w3.org/2000/svg"><path d="M6.25 4h11.5a3.25 3.25 0 0 1 3.245 3.066L21 7.25v9.5a3.25 3.25 0 0 1-3.066 3.245L17.75 20H6.25a3.25 3.25 0 0 1-3.245-3.066L3 16.75v-9.5a3.25 3.25 0 0 1 3.066-3.245L6.25 4h11.5-11.5Zm11.5 1.5H6.25a1.75 1.75 0 0 0-1.744 1.606L4.5 7.25v9.5a1.75 1.75 0 0 0 1.606 1.744l.144.006h11.5a1.75 1.75 0 0 0 1.744-1.607l.006-.143v-9.5a1.75 1.75 0 0 0-1.607-1.744L17.75 5.5Zm-7.697 4.085a.5.5 0 0 1 .587-.256l.084.033 4.382 2.19a.5.5 0 0 1 .076.848l-.076.047-4.382 2.191a.5.5 0 0 1-.716-.357L10 14.19V9.809a.5.5 0 0 1 .053-.224Z" fill="#212121"/></svg>
diff --git a/resources/icons/ui/zip.svg b/resources/icons/ui/zip.svg
new file mode 100644
index 0000000000000000000000000000000000000000..e22534d6d9eebafff9c690b2673e7409dbc0b20c
--- /dev/null
+++ b/resources/icons/ui/zip.svg
@@ -0,0 +1 @@
+<svg width="512" height="512" fill="none" viewBox="0 0 24 24" xmlns="http://www.w3.org/2000/svg"><path d="M9.49 4.402A2.25 2.25 0 0 0 8.208 4H4.25l-.154.005A2.25 2.25 0 0 0 2 6.25v11.5l.005.154A2.25 2.25 0 0 0 4.25 20h15.5l.154-.005A2.25 2.25 0 0 0 22 17.75v-9l-.005-.154-.017-.158A2.25 2.25 0 0 0 19.75 6.5h-7.728L9.647 4.521l-.156-.119ZM13.498 8v2.245c0 .414.335.75.75.75h.75v1.003h-.25a.75.75 0 0 0 0 1.5h.25v1.5h-.25a.75.75 0 0 0 0 1.5h.25V18.5H4.25l-.102-.007a.75.75 0 0 1-.648-.743v-7.251l4.707.001.196-.009a2.25 2.25 0 0 0 1.244-.512L12.021 8h1.476Zm3 10h.25a.75.75 0 0 0 0-1.5h-.25V15h.25a.75.75 0 0 0 0-1.5h-.25v-2.505h.75a.75.75 0 0 0 .75-.75V8h1.753l.102.007a.75.75 0 0 1 .648.743v9l-.007.102a.75.75 0 0 1-.743.648h-3.253V18Zm0-10v1.495h-1.5V8h1.5ZM4.25 5.5h3.957l.104.007a.75.75 0 0 1 .376.167l1.891 1.575-1.89 1.577-.086.061A.75.75 0 0 1 8.207 9L3.5 8.999V6.25l.007-.102A.75.75 0 0 1 4.25 5.5Z" fill="#212121"/></svg>
diff --git a/resources/qml/TimelineView.qml b/resources/qml/TimelineView.qml
index 0b3a6427edcb267c71b6c31b7100bc1b68e0d47d..7421d5942564a49dbfa0b88cb3a8accd3b44f083 100644
--- a/resources/qml/TimelineView.qml
+++ b/resources/qml/TimelineView.qml
@@ -124,10 +124,76 @@ Item {
             color: Nheko.theme.separator
         }
 
-        Button {
-            text: "Send files " + (room ? room.input.uploads.length : 0)
+
+        Page {
+            id: uploadPopup
             visible: room && room.input.uploads.length > 0
-            onClicked: room.input.acceptUploads()
+            Layout.preferredHeight: 200
+            clip: true
+
+            Layout.fillWidth: true
+
+            padding: Nheko.paddingMedium
+
+            contentItem: ListView {
+                id: uploadsList
+                anchors.horizontalCenter: parent.horizontalCenter
+                boundsBehavior: Flickable.StopAtBounds
+
+                orientation: ListView.Horizontal
+                width: Math.min(contentWidth, parent.width)
+                model: room ? room.input.uploads : undefined
+                spacing: Nheko.paddingMedium
+
+                delegate: Pane {
+                    padding: Nheko.paddingSmall
+                    height: uploadPopup.availableHeight - buttons.height
+                    width: uploadPopup.availableHeight - buttons.height
+
+                    background: Rectangle {
+                        color: Nheko.colors.window
+                        radius: Nheko.paddingMedium
+                    }
+                    contentItem: ColumnLayout {
+                        Image {
+                            Layout.fillHeight: true
+                            Layout.fillWidth: true
+
+                            sourceSize.height: height
+                            sourceSize.width: width
+
+                            property string typeStr: switch(modelData.mediaType) {
+                                case MediaUpload.Video: return "video-file";
+                                case MediaUpload.Audio: return "music";
+                                case MediaUpload.Image: return "image";
+                                default: return "zip";
+                            }
+                            source: "image://colorimage/:/icons/icons/ui/"+typeStr+".svg?" + Nheko.colors.buttonText
+                        }
+                        MatrixTextField {
+                            Layout.fillWidth: true
+                            text: modelData.filename
+                            onTextEdited: modelData.filename = text
+                        }
+                    }
+                }
+            }
+
+            footer: DialogButtonBox {
+                id: buttons
+
+                standardButtons: DialogButtonBox.Cancel
+                Button {
+                    text: qsTr("Upload %n file(s)", "", (room ? room.input.uploads.length : 0))
+                    DialogButtonBox.buttonRole: DialogButtonBox.AcceptRole
+                }
+                onAccepted: room.input.acceptUploads()
+                onRejected: room.input.declineUploads()
+            }
+
+            background: Rectangle {
+                color: Nheko.colors.base
+            }
         }
 
         NotificationWarning {
diff --git a/resources/qml/delegates/PlayableMediaMessage.qml b/resources/qml/delegates/PlayableMediaMessage.qml
index 405727044ff7040efa208c56649e5d9f4740fb6b..4828843cc0eeae44eac59dfa7427fdc38319886d 100644
--- a/resources/qml/delegates/PlayableMediaMessage.qml
+++ b/resources/qml/delegates/PlayableMediaMessage.qml
@@ -58,7 +58,7 @@ Item {
 
         Image {
             anchors.fill: parent
-            source: thumbnailUrl.replace("mxc://", "image://MxcImage/") + "?scale"
+            source: thumbnailUrl ? thumbnailUrl.replace("mxc://", "image://MxcImage/") + "?scale" : ""
             asynchronous: true
             fillMode: Image.PreserveAspectFit
 
diff --git a/resources/res.qrc b/resources/res.qrc
index a383f8054fee9d3d46aed4b1ae088ecf0fa08c0c..ad86c88d58c60e2a3796953bf207e4a3bc4d5fb5 100644
--- a/resources/res.qrc
+++ b/resources/res.qrc
@@ -46,6 +46,10 @@
         <file>icons/ui/volume-off-indicator.svg</file>
         <file>icons/ui/volume-up.svg</file>
         <file>icons/ui/world.svg</file>
+        <file>icons/ui/music.svg</file>
+        <file>icons/ui/image.svg</file>
+        <file>icons/ui/zip.svg</file>
+        <file>icons/ui/video-file.svg</file>
         <file>icons/emoji-categories/activity.svg</file>
         <file>icons/emoji-categories/flags.svg</file>
         <file>icons/emoji-categories/foods.svg</file>
diff --git a/src/MainWindow.cpp b/src/MainWindow.cpp
index 73e556f7362a3672021147d3f5ccefde43582c04..c4af7f0cea277f78c2539947d84d9d987505f3e3 100644
--- a/src/MainWindow.cpp
+++ b/src/MainWindow.cpp
@@ -251,6 +251,8 @@ MainWindow::registerQmlTypes()
     qmlRegisterType<emoji::EmojiModel>("im.nheko.EmojiModel", 1, 0, "EmojiModel");
     qmlRegisterUncreatableType<emoji::Emoji>(
       "im.nheko.EmojiModel", 1, 0, "Emoji", QStringLiteral("Used by emoji models"));
+    qmlRegisterUncreatableType<MediaUpload>(
+      "im.nheko", 1, 0, "MediaUpload", QStringLiteral("MediaUploads can not be created in Qml"));
     qmlRegisterUncreatableMetaObject(emoji::staticMetaObject,
                                      "im.nheko.EmojiModel",
                                      1,
diff --git a/src/timeline/InputBar.h b/src/timeline/InputBar.h
index 46563bbb4feea05ac1d86b181718bf1b48ba0824..4472fe84e67f75db5d302ccf415ea491300aae93 100644
--- a/src/timeline/InputBar.h
+++ b/src/timeline/InputBar.h
@@ -53,11 +53,11 @@ class MediaUpload : public QObject
 {
     Q_OBJECT
     //    Q_PROPERTY(bool uploading READ uploading NOTIFY uploadingChanged)
-    //    Q_PROPERTY(MediaType mediaType READ type NOTIFY mediaTypeChanged)
+    Q_PROPERTY(int mediaType READ type NOTIFY mediaTypeChanged)
     //    // https://stackoverflow.com/questions/33422265/pass-qimage-to-qml/68554646#68554646
     //    Q_PROPERTY(QUrl thumbnail READ thumbnail NOTIFY thumbnailChanged)
     //    Q_PROPERTY(QString humanSize READ humanSize NOTIFY huSizeChanged)
-    //    Q_PROPERTY(QString filename READ filename NOTIFY filenameChanged)
+    Q_PROPERTY(QString filename READ filename WRITE setFilename NOTIFY filenameChanged)
     //    Q_PROPERTY(QString mimetype READ mimetype NOTIFY mimetypeChanged)
     //    Q_PROPERTY(int height READ height NOTIFY heightChanged)
     //    Q_PROPERTY(int width READ width NOTIFY widthChanged)
@@ -73,7 +73,7 @@ public:
         Video,
         Audio,
     };
-    Q_ENUM(MediaType);
+    Q_ENUM(MediaType)
 
     explicit MediaUpload(std::unique_ptr<QIODevice> data,
                          QString mimetype,
@@ -81,6 +81,17 @@ public:
                          bool encrypt,
                          QObject *parent = nullptr);
 
+    [[nodiscard]] int type() const
+    {
+        if (mimeClass_ == u"video")
+            return MediaType::Video;
+        else if (mimeClass_ == u"audio")
+            return MediaType::Audio;
+        else if (mimeClass_ == u"image")
+            return MediaType::Image;
+        else
+            return MediaType::File;
+    }
     [[nodiscard]] QString url() const { return url_; }
     [[nodiscard]] QString mimetype() const { return mimetype_; }
     [[nodiscard]] QString mimeClass() const { return mimeClass_; }
@@ -102,9 +113,19 @@ public:
     QString thumbnailUrl() const { return thumbnailUrl_; }
     [[nodiscard]] uint64_t thumbnailSize() const { return thumbnailSize_; }
 
+    void setFilename(QString fn)
+    {
+        if (fn != originalFilename_) {
+            originalFilename_ = std::move(fn);
+            emit filenameChanged();
+        }
+    }
+
 signals:
     void uploadComplete(MediaUpload *self, QString url);
     void uploadFailed(MediaUpload *self);
+    void filenameChanged();
+    void mediaTypeChanged();
 
 public slots:
     void startUpload();