diff --git a/src/server/headed-mode-plugin.js b/src/server/headed-mode-plugin.js
index 2a371d1d..c167494a 100644
--- a/src/server/headed-mode-plugin.js
+++ b/src/server/headed-mode-plugin.js
@@ -1,4 +1,4 @@
-import { dirname, join } from 'node:path';
+import { dirname, posix } from 'node:path';
 import { globSync } from 'glob';
 
 export function headedMode({ open, watch, pattern }) {
@@ -9,7 +9,7 @@ export function headedMode({ open, watch, pattern }) {
 		name: 'brightspace-headed-mode',
 		async transform(context) {
 			if ((watch || open) && files.includes(context.path.slice(1))) {
-				const pausePath = join(dirname(import.meta.url), 'pause.js').replace('file:', '');
+				const pausePath = posix.join(dirname(import.meta.url), 'pause.js').replace(/file:(\/c:)?/i, '');
 				return `debugger;\nimport '${pausePath}'\n${context.body}`;
 			}
 		}