diff --git a/library/std/src/fs/tests.rs b/library/std/src/fs/tests.rs
index 13dbae3b7b58..628de13156c6 100644
--- a/library/std/src/fs/tests.rs
+++ b/library/std/src/fs/tests.rs
@@ -1411,3 +1411,32 @@ fn symlink_hard_link() {
     // "hard_link" should still appear as a symlink.
     assert!(check!(fs::symlink_metadata(tmpdir.join("hard_link"))).file_type().is_symlink());
 }
+
+/// Ensure `fs::create_dir` works on Windows with longer paths.
+#[test]
+#[cfg(windows)]
+fn create_dir_long_paths() {
+    use crate::{ffi::OsStr, iter, os::windows::ffi::OsStrExt};
+    const PATH_LEN: usize = 247;
+
+    let tmpdir = tmpdir();
+    let mut path = tmpdir.path().to_path_buf();
+    path.push("a");
+    let mut path = path.into_os_string();
+
+    let utf16_len = path.encode_wide().count();
+    if utf16_len >= PATH_LEN {
+        // Skip the test in the unlikely event the local user has a long temp directory path.
+        // This should not affect CI.
+        return;
+    }
+    // Increase the length of the path.
+    path.extend(iter::repeat(OsStr::new("a")).take(PATH_LEN - utf16_len));
+
+    // This should succeed.
+    fs::create_dir(&path).unwrap();
+
+    // This will fail if the path isn't converted to verbatim.
+    path.push("a");
+    fs::create_dir(&path).unwrap();
+}
diff --git a/library/std/src/sys/windows/path.rs b/library/std/src/sys/windows/path.rs
index eea7f3247c06..ad3f44fee8d7 100644
--- a/library/std/src/sys/windows/path.rs
+++ b/library/std/src/sys/windows/path.rs
@@ -150,7 +150,11 @@ fn parse_next_component(path: &OsStr, verbatim: bool) -> (&OsStr, &OsStr) {
 ///
 /// This path may or may not have a verbatim prefix.
 pub(crate) fn maybe_verbatim(path: &Path) -> io::Result<Vec<u16>> {
-    const LEGACY_MAX_PATH: usize = 260;
+    // Normally the MAX path is 260 UTF-16 code units (including the NULL).
+    // However, for APIs such as CreateDirectory[1], the limit is 248.
+    //
+    // [1]: https://docs.microsoft.com/en-us/windows/win32/api/fileapi/nf-fileapi-createdirectorya#parameters
+    const LEGACY_MAX_PATH: usize = 248;
     // UTF-16 encoded code points, used in parsing and building UTF-16 paths.
     // All of these are in the ASCII range so they can be cast directly to `u16`.
     const SEP: u16 = b'\\' as _;
diff --git a/library/std/src/sys/windows/path/tests.rs b/library/std/src/sys/windows/path/tests.rs
index 131d27a99fee..c6c84519f419 100644
--- a/library/std/src/sys/windows/path/tests.rs
+++ b/library/std/src/sys/windows/path/tests.rs
@@ -81,6 +81,13 @@ fn verbatim() {
     check(r"\\server\share", r"\\server\share");
     check(r"\\.\COM1", r"\\.\COM1");
 
+    // Check that paths of length 247 are converted to verbatim.
+    // This is necessary for `CreateDirectory`.
+    check(
+        r"C:\aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa",
+        r"\\?\C:\aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa",
+    );
+
     // Make sure opening a drive will work.
     check("Z:", "Z:");