diff --git a/TODO.md b/TODO.md
index 6535b6b6..d1f41422 100644
--- a/TODO.md
+++ b/TODO.md
@@ -1,5 +1,6 @@
 # TODO
 
+- power control focus
 - idlemanager: what if setPresence call fails due to network?
 - block power level change when offline
 - fix power level control button layout when apply button is loading
@@ -158,7 +159,6 @@
 
 - Add upload keybindings (close failed upload, pause, resume)
 - Handle errors when setting an avatar
-- Show confirmation box when picking file to upload or uploading from clipboard
 - Show proper progress ring for mxc thumbnails loading
 
 - Sentinel function to report local file paths for already downloaded media,
diff --git a/src/gui/Pages/Chat/Composer/UploadButton.qml b/src/gui/Pages/Chat/Composer/UploadButton.qml
index 00390b66..ce2cb164 100644
--- a/src/gui/Pages/Chat/Composer/UploadButton.qml
+++ b/src/gui/Pages/Chat/Composer/UploadButton.qml
@@ -21,8 +21,14 @@ HButton {
 
     HShortcut {
         sequences: window.settings.keys.sendFileFromPathInClipboard
-        onActivated: utils.sendFile(
-            chat.userId, chat.roomId, Clipboard.text.trim(),
+        onActivated: utils.makePopup(
+            "Popups/ConfirmUploadPopup.qml",
+            {
+                userId: chat.userId,
+                roomId: chat.roomId,
+                roomName: chat.roomInfo.display_name,
+                filePath: Clipboard.text.trim(),
+            },
         )
     }
 
diff --git a/src/gui/Popups/ConfirmUploadPopup.qml b/src/gui/Popups/ConfirmUploadPopup.qml
new file mode 100644
index 00000000..523cf53a
--- /dev/null
+++ b/src/gui/Popups/ConfirmUploadPopup.qml
@@ -0,0 +1,62 @@
+// SPDX-License-Identifier: LGPL-3.0-or-later
+
+import QtQuick 2.12
+import QtQuick.Controls 2.12
+import QtQuick.Layouts 1.12
+import "../Base"
+import "../Base/Buttons"
+
+HColumnPopup {
+    id: popup
+
+    property string userId
+    property string roomId
+    property string roomName
+    property string filePath
+
+    readonly property string fileName: filePath.split("/").slice(-1)[0]
+
+
+    page.footer: AutoDirectionLayout {
+        ApplyButton {
+            id: uploadButton
+            text: qsTr("Send")
+            icon.name: "confirm-uploading-file"
+            onClicked: {
+                utils.sendFile(popup.userId, popup.roomId, filePath)
+                popup.close()
+            }
+        }
+
+        CancelButton {
+            id: cancelButton
+            onClicked: popup.close()
+        }
+    }
+
+    onOpened: uploadButton.forceActiveFocus()
+
+    SummaryLabel {
+        text:
+            qsTr("Send %1 to %2?")
+            .arg(utils.htmlColorize(fileName, theme.colors.accentText))
+            .arg(utils.htmlColorize(roomName, theme.colors.accentText))
+
+        textFormat: Text.StyledText
+    }
+
+    HImage {
+        source: popup.filePath
+        fillMode: Image.PreserveAspectFit
+        visible: status !== Image.Error
+
+        Layout.fillWidth: true
+        Layout.fillHeight: true
+        Layout.preferredHeight:
+            status === Image.Ready ?
+            width / (implicitWidth / implicitHeight) :
+            0
+
+        Behavior on Layout.preferredHeight { HNumberAnimation {} }
+    }
+}
diff --git a/src/gui/Utils.qml b/src/gui/Utils.qml
index 1de9ab02..2f2d827a 100644
--- a/src/gui/Utils.qml
+++ b/src/gui/Utils.qml
@@ -191,6 +191,11 @@ QtObject {
     }
 
 
+    function htmlColorize(text, color) {
+        return `<font color="${color}">${text}</font>`
+    }
+
+
     function processedEventText(ev) {
         const type       = ev.event_type
         const unknownMsg = type === "RoomMessageUnknown"
diff --git a/src/icons/thin/confirm-uploading-file.svg b/src/icons/thin/confirm-uploading-file.svg
new file mode 100644
index 00000000..2eed4d1d
--- /dev/null
+++ b/src/icons/thin/confirm-uploading-file.svg
@@ -0,0 +1,3 @@
+<svg height="24" viewBox="0 0 24 24" width="24" xmlns="http://www.w3.org/2000/svg">
+    <path d="m24 0-6 22-8.129-7.239 7.802-8.234-10.458 7.227-7.215-1.754zm-15 16.668v7.332l3.258-4.431z"/>
+</svg>