diff --git a/playwright/e2e/file-upload/image-upload.spec.ts b/playwright/e2e/file-upload/image-upload.spec.ts
new file mode 100644
index 0000000000..8f0403af31
--- /dev/null
+++ b/playwright/e2e/file-upload/image-upload.spec.ts
@@ -0,0 +1,45 @@
+/*
+Copyright 2024 The Matrix.org Foundation C.I.C.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+import { test, expect } from "../../element-web-test";
+
+test.describe("Image Upload", () => {
+    test.use({
+        displayName: "Alice",
+    });
+
+    test.beforeEach(async ({ page, app, user }) => {
+        await app.client.createRoom({ name: "My Pictures" });
+        await app.viewRoomByName("My Pictures");
+
+        // Wait until configuration is finished
+        await expect(
+            page
+                .locator(".mx_GenericEventListSummary[data-layout='group'] .mx_GenericEventListSummary_summary")
+                .getByText(`${user.displayName} created and configured the room.`),
+        ).toBeVisible();
+    });
+
+    test("should show image preview when uploading an image", async ({ page, app }) => {
+        await page
+            .locator(".mx_MessageComposer_actions input[type='file']")
+            .setInputFiles("playwright/sample-files/riot.png");
+
+        expect(page.getByRole("button", { name: "Upload" })).toBeEnabled();
+        expect(page.getByRole("button", { name: "Close dialog" })).toBeEnabled();
+        expect(page).toMatchScreenshot("image-upload-preview.png");
+    });
+});
diff --git a/playwright/snapshots/file-upload/image-upload.spec.ts/image-upload-preview-linux.png b/playwright/snapshots/file-upload/image-upload.spec.ts/image-upload-preview-linux.png
new file mode 100644
index 0000000000..75a9c353de
Binary files /dev/null and b/playwright/snapshots/file-upload/image-upload.spec.ts/image-upload-preview-linux.png differ
diff --git a/res/css/_common.pcss b/res/css/_common.pcss
index 122400c43f..d120194491 100644
--- a/res/css/_common.pcss
+++ b/res/css/_common.pcss
@@ -333,7 +333,7 @@ legend {
     z-index: var(--dialog-zIndex-standard);
     position: relative;
     width: 100%;
-    max-width: min-content;
+    max-width: fit-content;
     box-sizing: border-box;
     max-height: calc(100% - var(--cpd-space-6x));
     display: flex;