Expand long filename error hints on Windows (#13490)

Windows (or at least NTFS) isn't able to cope with paths where any
*segment* is longer than 255 characters, even if Long Path Support is
enabled. Update the hints provided on OS errors on Windows to reflect
this possibility.

Author: sepehr-rs

news/13346.bugfix.rst

@@ -0,0 +1 @@
+Provide a hint if a system error is raised involving long filenames or path segments on Windows.

src/pip/_internal/commands/install.py

@@ -7,6 +7,7 @@
 import shutil
 import site
 from optparse import SUPPRESS_HELP, Values
+from pathlib import Path
 
 from pip._vendor.packaging.utils import canonicalize_name
 from pip._vendor.requests.exceptions import InvalidProxyURL
@@ -774,20 +775,24 @@ def create_os_error_message(
         )
         parts.append(".\n")
 
-    # Suggest the user to enable Long Paths if path length is
-    # more than 260
-    if (
-        WINDOWS
-        and error.errno == errno.ENOENT
-        and error.filename
-        and len(error.filename) > 260
-    ):
-        parts.append(
-            "HINT: This error might have occurred since "
-            "this system does not have Windows Long Path "
-            "support enabled. You can find information on "
-            "how to enable this at "
-            "https://pip.pypa.io/warnings/enable-long-paths\n"
-        )
+    # On Windows, errors like EINVAL or ENOENT may occur
+    # if a file or folder name exceeds 255 characters,
+    # or if the full path exceeds 260 characters and long path support isn't enabled.
+    # This condition checks for such cases and adds a hint to the error output.
 
+    if WINDOWS and error.errno in (errno.EINVAL, errno.ENOENT) and error.filename:
+        if any(len(part) > 255 for part in Path(error.filename).parts):
+            parts.append(
+                "HINT: This error might be caused by a file or folder name exceeding "
+                "255 characters, which is a Windows limitation even if long paths "
+                "are enabled.\n "
+            )
+        if len(error.filename) > 260:
+            parts.append(
+                "HINT: This error might have occurred since "
+                "this system does not have Windows Long Path "
+                "support enabled. You can find information on "
+                "how to enable this at "
+                "https://pip.pypa.io/warnings/enable-long-paths\n"
+            )
     return "".join(parts).strip() + "\n"

tests/unit/test_command_install.py

@@ -1,4 +1,5 @@
 import errno
+import sys
 from unittest import mock
 
 import pytest
@@ -120,6 +121,56 @@ def test_most_cases(
             "Consider checking your local proxy configuration"
             ' with "pip config debug".\n',
         ),
+        # Testing both long path error (ENOENT)
+        # and long file/folder name error (EINVAL) on Windows
+        pytest.param(
+            OSError(errno.ENOENT, "No such file or directory", f"C:{'/a'*261}"),
+            False,
+            False,
+            "Could not install packages due to an OSError: "
+            f"[Errno 2] No such file or directory: 'C:{'/a'*261}'\n"
+            "HINT: This error might have occurred since "
+            "this system does not have Windows Long Path "
+            "support enabled. You can find information on "
+            "how to enable this at "
+            "https://pip.pypa.io/warnings/enable-long-paths\n",
+            marks=pytest.mark.skipif(
+                sys.platform != "win32", reason="Windows-specific filename length test"
+            ),
+        ),
+        pytest.param(
+            OSError(errno.EINVAL, "No such file or directory", f"C:/{'a'*256}"),
+            False,
+            False,
+            "Could not install packages due to an OSError: "
+            f"[Errno 22] No such file or directory: 'C:/{'a'*256}'\n"
+            "HINT: This error might be caused by a file or folder name exceeding "
+            "255 characters, which is a Windows limitation even if long paths "
+            "are enabled.\n",
+            marks=pytest.mark.skipif(
+                sys.platform != "win32", reason="Windows-specific filename length test"
+            ),
+        ),
+        pytest.param(
+            OSError(
+                errno.EINVAL, "No such file or directory", f"C:{'/a'*261}/{'b'*256}"
+            ),
+            False,
+            False,
+            "Could not install packages due to an OSError: "
+            f"[Errno 22] No such file or directory: 'C:{'/a' * 261}/{'b' * 256}'\n"
+            "HINT: This error might be caused by a file or folder name exceeding "
+            "255 characters, which is a Windows limitation even if long paths "
+            "are enabled.\n "
+            "HINT: This error might have occurred since "
+            "this system does not have Windows Long Path "
+            "support enabled. You can find information on "
+            "how to enable this at "
+            "https://pip.pypa.io/warnings/enable-long-paths\n",
+            marks=pytest.mark.skipif(
+                sys.platform != "win32", reason="Windows-specific filename length test"
+            ),
+        ),
     ],
 )
 def test_create_os_error_message(