diff --git a/libs/node_resolver/resolution.rs b/libs/node_resolver/resolution.rs
index 47de40278c..b0b10e32ce 100644
--- a/libs/node_resolver/resolution.rs
+++ b/libs/node_resolver/resolution.rs
@@ -553,10 +553,9 @@ impl<
     // }
 
     let p_str = path.to_str().unwrap();
-    let path = if p_str.ends_with('/') {
-      PathBuf::from(&p_str[p_str.len() - 1..])
-    } else {
-      path
+    let path = match p_str.strip_suffix('/') {
+      Some(s) => Cow::Borrowed(Path::new(s)),
+      None => Cow::Owned(path),
     };
 
     let maybe_file_type = self.sys.get_file_type(&path);
@@ -570,7 +569,7 @@ impl<
             .find(|e| self.sys.is_file(&path.join(e)));
           Err(
             UnsupportedDirImportError {
-              dir_url: UrlOrPath::Path(path),
+              dir_url: UrlOrPath::Path(path.into_owned()),
               maybe_referrer: maybe_referrer.map(|r| r.display()),
               suggested_file_name,
             }
@@ -607,7 +606,7 @@ impl<
         Ok(
           maybe_url
             .map(UrlOrPath::Url)
-            .unwrap_or(UrlOrPath::Path(path)),
+            .unwrap_or(UrlOrPath::Path(path.into_owned())),
         )
       }
       _ => {
@@ -626,7 +625,7 @@ impl<
           ModuleNotFoundError {
             suggested_ext: self
               .module_not_found_ext_suggestion(&path, resolved_method),
-            specifier: UrlOrPath::Path(path),
+            specifier: UrlOrPath::Path(path.into_owned()),
             maybe_referrer: maybe_referrer.map(|r| r.display()),
           }
           .into(),
diff --git a/tests/specs/bundle/require_dotdot/__test__.jsonc b/tests/specs/bundle/require_dotdot/__test__.jsonc
new file mode 100644
index 0000000000..1dcf32ec04
--- /dev/null
+++ b/tests/specs/bundle/require_dotdot/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "bundle -o out.js ./repro/foo.cjs",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": "run -A out.js",
+      "output": "hello from index\n"
+    }
+  ]
+}
diff --git a/tests/specs/bundle/require_dotdot/index.js b/tests/specs/bundle/require_dotdot/index.js
new file mode 100644
index 0000000000..a67a5209e7
--- /dev/null
+++ b/tests/specs/bundle/require_dotdot/index.js
@@ -0,0 +1 @@
+module.exports = "hello from index";
diff --git a/tests/specs/bundle/require_dotdot/package.json b/tests/specs/bundle/require_dotdot/package.json
new file mode 100644
index 0000000000..0967ef424b
--- /dev/null
+++ b/tests/specs/bundle/require_dotdot/package.json
@@ -0,0 +1 @@
+{}
diff --git a/tests/specs/bundle/require_dotdot/repro/foo.cjs b/tests/specs/bundle/require_dotdot/repro/foo.cjs
new file mode 100644
index 0000000000..61ad270acd
--- /dev/null
+++ b/tests/specs/bundle/require_dotdot/repro/foo.cjs
@@ -0,0 +1,2 @@
+const index = require("..");
+console.log(index);