diff --git a/ext/fs/std_fs.rs b/ext/fs/std_fs.rs
index 4845e9c7bc..eb0b4ce5ec 100644
--- a/ext/fs/std_fs.rs
+++ b/ext/fs/std_fs.rs
@@ -1063,7 +1063,7 @@ fn open_options(options: OpenOptions) -> fs::OpenOptions {
 }
 
 #[inline(always)]
-fn open_with_access_check(
+pub fn open_with_access_check(
   options: OpenOptions,
   path: &Path,
   access_check: Option<AccessCheckCb>,
@@ -1071,7 +1071,11 @@ fn open_with_access_check(
   if let Some(access_check) = access_check {
     let path_bytes = path.as_os_str().as_encoded_bytes();
     let is_windows_device_path = cfg!(windows)
-      && path_bytes.starts_with(br"\\.\")
+      && (path_bytes.starts_with(br"\\.\")
+        || path_bytes.starts_with(b"//./")
+        || path_bytes.starts_with(b"//?/")
+        || path_bytes.starts_with(br"\\?\")
+        || path_bytes.ends_with(b"$"))
       && !path_bytes.contains(&b':');
     let path = if is_windows_device_path {
       // On Windows, normalize_path doesn't work with device-prefix-style
diff --git a/tests/specs/eval/check_device_paths/__test__.jsonc b/tests/specs/eval/check_device_paths/__test__.jsonc
new file mode 100644
index 0000000000..047fc4d985
--- /dev/null
+++ b/tests/specs/eval/check_device_paths/__test__.jsonc
@@ -0,0 +1,63 @@
+{
+  "tempDir": true,
+  "tests": {
+    "valid_device_paths": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('CONOUT$',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: true }\n"
+    },
+    "valid_device_paths_i": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('CONIN$',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: true }\n"
+    },
+    "valid_device_paths_with_prefix": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//./CONOUT$',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: true }\n"
+    },
+    "valid_device_paths_with_prefix_i": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//./CONIN$',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: true }\n"
+    },
+    "valid_device_paths_with_prefix_ii": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//?/CONIN$',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: true }\n"
+    },
+    "valid_device_paths_with_prefix_iii": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//?/CONOUT$',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: true }\n"
+    },
+    "valid_device_paths_nul_i": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//./NUL',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: false }\n"
+    },
+    "valid_device_paths_nul_ii": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//?/NUL',{read:true,write:true}).isTerminal()})",
+      "output": "{ isTTY: false }\n"
+    },
+    "invalid_device_paths": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('\\\\.\\INVALID$',{read:true,write:true}).isTerminal()})",
+      "output": "error: Uncaught (in promise) NotFound: The system cannot find the file specified. (os error 2): open '\\.INVALID$'\n[WILDCARD]",
+      "exitCode": 1
+    },
+    "invalid_device_paths_i": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('//./INVALID$',{read:true,write:true}).isTerminal()})",
+      "output": "error: Uncaught (in promise) NotFound: The system cannot find the file specified. (os error 2): open '//./INVALID$'\n[WILDCARD]",
+      "exitCode": 1
+    },
+    "invalid_device_paths_ii": {
+      "if": "windows",
+      "args": "eval console.log({isTTY:Deno.openSync('C:\\Invalid\\Path',{read:true,write:true}).isTerminal()})",
+      "output": "error: Uncaught (in promise) NotFound: The system cannot find the file specified. (os error 2): open 'C:InvalidPath'\n[WILDCARD]",
+      "exitCode": 1
+    }
+  }
+}