diff --git a/src/wp-admin/async-upload.php b/src/wp-admin/async-upload.php
index 683fd83248..2ac2f20e76 100644
--- a/src/wp-admin/async-upload.php
+++ b/src/wp-admin/async-upload.php
@@ -112,10 +112,12 @@ if ( isset( $_REQUEST['post_id'] ) ) {
 
 $id = media_handle_upload( 'async-upload', $post_id );
 if ( is_wp_error( $id ) ) {
-	$message = sprintf(
+	$button_unique_id = uniqid( 'dismiss-' );
+	$message          = sprintf(
 		'%s <strong>%s</strong><br />%s',
 		sprintf(
-			'<button type="button" class="dismiss button-link" onclick="jQuery(this).parents(\'div.media-item\').slideUp(200, function(){jQuery(this).remove();});">%s</button>',
+			'<button type="button" id="%s" class="dismiss button-link">%s</button>',
+			esc_attr( $button_unique_id ),
 			__( 'Dismiss' )
 		),
 		sprintf(
@@ -132,6 +134,7 @@ if ( is_wp_error( $id ) ) {
 			'paragraph_wrap'     => false,
 		)
 	);
+	echo "<script>jQuery( 'button#{$button_unique_id}' ).on( 'click', function() {jQuery(this).parents('div.media-item').slideUp(200, function(){jQuery(this).remove();})});</script>\n";
 	exit;
 }
 
diff --git a/tests/e2e/assets/sample.svg b/tests/e2e/assets/sample.svg
new file mode 100644
index 0000000000..faccd78697
--- /dev/null
+++ b/tests/e2e/assets/sample.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="800" height="450" viewBox="0 0 800 450"> <rect fill="#0F1C3F" width="800" height="450"/> <text fill="#7FDBFF" font-family="sans-serif" font-size="90" dy="31.499999999999996" font-weight="bold" x="50%" y="50%" text-anchor="middle">800×450</text> </svg>
\ No newline at end of file
diff --git a/tests/e2e/specs/media-upload.test.js b/tests/e2e/specs/media-upload.test.js
new file mode 100644
index 0000000000..885dee92c9
--- /dev/null
+++ b/tests/e2e/specs/media-upload.test.js
@@ -0,0 +1,35 @@
+/**
+ * WordPress dependencies
+ */
+import { test, expect } from '@wordpress/e2e-test-utils-playwright';
+
+/**
+ * External dependencies
+ */
+import path from 'path';
+
+test( 'Test dismissing failed upload works correctly', async ({ page, admin, requestUtils }) => {
+	// Log in before visiting admin page.
+	await requestUtils.login();
+	await admin.visitAdminPage( '/media-new.php' );
+
+	// It takes a moment for the multi-file uploader to become available.
+	await page.waitForLoadState('load');
+
+	const testImagePath = path.join(__dirname, '../assets/sample.svg');
+
+	// Upload a file that will fail.
+	const input = page.locator( '#plupload-upload-ui input[type="file"]' );
+	await input.setInputFiles( testImagePath );
+
+	// Ensure the error message is visible.
+	await expect(
+		page.getByText('“sample.svg” has failed to upload.')
+	).toBeVisible();
+
+	// Ensure the error message is dismissed.
+	await page.getByRole('button', { name: 'Dismiss' }).click();
+	await expect(
+		page.getByText('“sample.svg” has failed to upload.')
+	).not.toBeVisible();
+} );