diff --git a/cli/standalone/virtual_fs.rs b/cli/standalone/virtual_fs.rs
index 5b8076549d1700..b630f629c5a8f0 100644
--- a/cli/standalone/virtual_fs.rs
+++ b/cli/standalone/virtual_fs.rs
@@ -329,7 +329,7 @@ impl VfsBuilder {
     let dir = self.add_dir(path.parent().unwrap())?;
     let name = path.file_name().unwrap().to_string_lossy();
     match dir.entries.binary_search_by(|e| e.name().cmp(&name)) {
-      Ok(_) => unreachable!(),
+      Ok(_) => Ok(()), // previously inserted
       Err(insert_index) => {
         dir.entries.insert(
           insert_index,
@@ -341,9 +341,9 @@ impl VfsBuilder {
               .collect::<Vec<_>>(),
           }),
         );
+        Ok(())
       }
     }
-    Ok(())
   }
 
   pub fn into_dir_and_files(self) -> (VirtualDirectory, Vec<Vec<u8>>) {
diff --git a/tests/specs/compile/include/symlink_twice/__test__.jsonc b/tests/specs/compile/include/symlink_twice/__test__.jsonc
new file mode 100644
index 00000000000000..ebdf824f43cf84
--- /dev/null
+++ b/tests/specs/compile/include/symlink_twice/__test__.jsonc
@@ -0,0 +1,27 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "args": "run -A setup.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "args": "compile --allow-read=data --include . --output main link.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "1\n",
+    "exitCode": 0
+  }, {
+    "if": "windows",
+    "args": "compile --allow-read=data --include . --output main.exe link.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "1\n",
+    "exitCode": 0
+  }]
+}
diff --git a/tests/specs/compile/include/symlink_twice/setup.js b/tests/specs/compile/include/symlink_twice/setup.js
new file mode 100644
index 00000000000000..3e713dd63e918a
--- /dev/null
+++ b/tests/specs/compile/include/symlink_twice/setup.js
@@ -0,0 +1,3 @@
+Deno.mkdirSync("data");
+Deno.writeTextFileSync("index.js", "console.log(1);");
+Deno.symlinkSync("index.js", "link.js");