diff --git a/src/js/_enqueues/vendor/plupload/wp-plupload.js b/src/js/_enqueues/vendor/plupload/wp-plupload.js
index c0eb570657bf4..3f648e94549f2 100644
--- a/src/js/_enqueues/vendor/plupload/wp-plupload.js
+++ b/src/js/_enqueues/vendor/plupload/wp-plupload.js
@@ -484,8 +484,14 @@ window.wp = window.wp || {};
 			return pluploadL10n.file_exceeds_size_limit.replace( '%s', file.name );
 		},
 
-		'HTTP_ERROR': function( file ) {
-			if ( file.type && file.type.indexOf( 'image/' ) === 0 ) {
+		'HTTP_ERROR': function( file, error ) {
+			var status = error && error.status;
+
+			if (
+				file.type &&
+				file.type.indexOf( 'image/' ) === 0 &&
+				! ( status >= 400 && status < 500 )
+			) {
 				return pluploadL10n.http_error_image;
 			}
 
diff --git a/tests/e2e/specs/media-upload.test.js b/tests/e2e/specs/media-upload.test.js
index 885dee92c915d..76ea1036df81f 100644
--- a/tests/e2e/specs/media-upload.test.js
+++ b/tests/e2e/specs/media-upload.test.js
@@ -3,12 +3,25 @@
  */
 import { test, expect } from '@wordpress/e2e-test-utils-playwright';
 
-/**
- * External dependencies
- */
-import path from 'path';
+/**
+ * External dependencies
+ */
+import { readFileSync } from 'node:fs';
+import path from 'path';
+
+const testImage = {
+	name: "test'image.jpg",
+	mimeType: 'image/jpeg',
+	buffer: readFileSync(
+		path.join( __dirname, '../../phpunit/data/images/test-image.jpg' )
+	),
+};
+
+test.afterEach( async ( { requestUtils } ) => {
+	await requestUtils.deleteAllMedia();
+} );
 
-test( 'Test dismissing failed upload works correctly', async ({ page, admin, requestUtils }) => {
+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' );
@@ -31,5 +44,77 @@ test( 'Test dismissing failed upload works correctly', async ({ page, admin, req
 	await page.getByRole('button', { name: 'Dismiss' }).click();
 	await expect(
 		page.getByText('“sample.svg” has failed to upload.')
-	).not.toBeVisible();
-} );
+	).not.toBeVisible();
+} );
+
+test( 'uploads an image with an apostrophe in its filename', async ( {
+	page,
+	admin,
+	requestUtils,
+} ) => {
+	await requestUtils.login();
+	await requestUtils.deleteAllMedia();
+	await admin.visitAdminPage( '/media-new.php' );
+	await page.waitForLoadState( 'load' );
+
+	const input = page.locator( '#plupload-upload-ui input[type="file"]' );
+	await input.setInputFiles( testImage );
+
+	await expect(
+		page.getByText( 'testimage.jpg', { exact: true } )
+	).toBeVisible();
+} );
+
+test( 'uses the generic HTTP error for a rejected image upload', async ( {
+	page,
+	admin,
+	requestUtils,
+} ) => {
+	await requestUtils.login();
+	await page.route( '**/wp-admin/async-upload.php', ( route ) =>
+		route.fulfill( {
+			status: 403,
+			contentType: 'text/plain',
+			body: 'Forbidden',
+		} )
+	);
+	await admin.visitAdminPage( '/media-new.php' );
+	await page.waitForLoadState( 'load' );
+
+	const input = page.locator( '#plupload-upload-ui input[type="file"]' );
+	await input.setInputFiles( testImage );
+
+	await expect(
+		page.getByText( 'Unexpected response from the server.' )
+	).toBeVisible();
+	await expect(
+		page.getByText( 'Suggested maximum size is 2560 pixels.' )
+	).not.toBeVisible();
+} );
+
+test( 'retains the image processing error for a server failure', async ( {
+	page,
+	admin,
+	requestUtils,
+} ) => {
+	await requestUtils.login();
+	await page.route( '**/wp-admin/async-upload.php', ( route ) =>
+		route.fulfill( {
+			status: 500,
+			contentType: 'text/plain',
+			body: 'Internal Server Error',
+		} )
+	);
+	await admin.visitAdminPage( '/media-new.php' );
+	await page.waitForLoadState( 'load' );
+
+	const input = page.locator( '#plupload-upload-ui input[type="file"]' );
+	await input.setInputFiles( testImage );
+
+	await expect(
+		page.getByText( 'The server cannot process the image.' )
+	).toBeVisible();
+	await expect(
+		page.getByText( 'Suggested maximum size is 2560 pixels.' )
+	).toBeVisible();
+} );