diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 198afb3a7689f2..afed0f04714af5 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -41,6 +41,7 @@ const {
   SafeMap,
   String,
   StringPrototypeIndexOf,
+  StringPrototypeLastIndexOf,
   StringPrototypeMatch,
   StringPrototypeSlice,
   StringPrototypeStartsWith,
@@ -287,12 +288,13 @@ function readPackageScope(checkPath) {
   const rootSeparatorIndex = checkPath.indexOf(path.sep);
   let separatorIndex;
   while (
-    (separatorIndex = checkPath.lastIndexOf(path.sep)) > rootSeparatorIndex
+    (separatorIndex = StringPrototypeLastIndexOf(checkPath, path.sep)) >=
+     rootSeparatorIndex
   ) {
     checkPath = checkPath.slice(0, separatorIndex);
     if (checkPath.endsWith(path.sep + 'node_modules'))
       return false;
-    const pjson = readPackage(checkPath);
+    const pjson = readPackage(checkPath + path.sep);
     if (pjson) return {
       path: checkPath,
       data: pjson