diff --git a/Misc/NEWS.d/next/Windows/2020-06-12-15-29-18.bpo-27729.nNXQot.rst b/Misc/NEWS.d/next/Windows/2020-06-12-15-29-18.bpo-27729.nNXQot.rst
new file mode 100644
index 00000000000..695200ef7cc
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2020-06-12-15-29-18.bpo-27729.nNXQot.rst
@@ -0,0 +1 @@
+Give a better error message when a file path is too long on Windows.
diff --git a/Python/errors.c b/Python/errors.c
index 5d1725679c4..31de0dbce1e 100644
--- a/Python/errors.c
+++ b/Python/errors.c
@@ -700,7 +700,11 @@ PyErr_SetFromErrnoWithFilenameObjects(PyObject *exc, PyObject *filenameObject, P
            table, we use it, otherwise we assume it really _is_
            a Win32 error code
         */
-        if (i > 0 && i < _sys_nerr) {
+        if (i == ENOENT && GetLastError() == ERROR_PATH_NOT_FOUND) {
+            message = PyUnicode_FromString("No such path or path exceeds "
+                                           "maximum allowed length");
+        }
+        else if (i > 0 && i < _sys_nerr) {
             message = PyUnicode_FromString(_sys_errlist[i]);
         }
         else {