diff --git a/fs/globrex.ts b/fs/globrex.ts
index a520009d83a8d..b866944d9837d 100644
--- a/fs/globrex.ts
+++ b/fs/globrex.ts
@@ -268,9 +268,9 @@ export function globrex(
         let isGlobstar =
           starCount > 1 && // multiple "*"'s
           // from the start of the segment
-          (prevChar === SEP_RAW || prevChar === undefined) &&
+          [SEP_RAW, "/", undefined].includes(prevChar) &&
           // to the end of the segment
-          (nextChar === SEP_RAW || nextChar === undefined);
+          [SEP_RAW, "/", undefined].includes(nextChar);
         if (isGlobstar) {
           // it's a globstar, so match zero or more path segments
           add(GLOBSTAR, { only: "regex" });
diff --git a/testing/runner.ts b/testing/runner.ts
index c4b04c58c9941..35781874a50a2 100755
--- a/testing/runner.ts
+++ b/testing/runner.ts
@@ -54,6 +54,8 @@ function partition(
 }
 
 function expandDirectory(dir: string, options: ExpandGlobOptions): WalkInfo[] {
+  console.log('expand glob', join(dir, DIR_GLOBS[0]));
+  console.log(glob(join(dir, DIR_GLOBS[0]), options));
   return DIR_GLOBS.flatMap((s: string): WalkInfo[] => [
     ...expandGlobSync(s, { ...options, root: dir })
   ]);