diff --git a/news/13346.bugfix.rst b/news/13346.bugfix.rst
new file mode 100644
index 00000000000..b2b9413e7b4
--- /dev/null
+++ b/news/13346.bugfix.rst
@@ -0,0 +1 @@
+Provide a hint if a system error is raised involving long filenames or path segments on Windows.
diff --git a/src/pip/_internal/commands/install.py b/src/pip/_internal/commands/install.py
index 056eb8866a0..5cb9e6f3b00 100644
--- a/src/pip/_internal/commands/install.py
+++ b/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
@@ -774,9 +775,23 @@ def create_os_error_message(
         )
         parts.append(".\n")
 
+    # Windows raises EINVAL when a file*name* or path segment exceeds 255
+    # characters, even if long path support is enabled.
+    if (
+        WINDOWS
+        and error.errno in (errno.EINVAL, errno.ENOENT)
+        and error.filename
+        and 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 "
+        )
+
     # Suggest the user to enable Long Paths if path length is
     # more than 260
-    if (
+    elif (
         WINDOWS
         and error.errno == errno.ENOENT
         and error.filename
diff --git a/tests/unit/test_command_install.py b/tests/unit/test_command_install.py
index e28edf6449c..db288cf0f4c 100644
--- a/tests/unit/test_command_install.py
+++ b/tests/unit/test_command_install.py
@@ -1,4 +1,5 @@
 import errno
+import sys
 from unittest import mock
 
 import pytest
@@ -120,6 +121,36 @@ 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:/foo/{'/a/'*261}"),
+            False,
+            False,
+            "Could not install packages due to an OSError: "
+            f"[Errno 2] No such file or directory: 'C:/foo/{'/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:/foo/{'a'*256}"),
+            False,
+            False,
+            "Could not install packages due to an OSError: "
+            f"[Errno 22] No such file or directory: 'C:/foo/{'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"
+            ),
+        ),
     ],
 )
 def test_create_os_error_message(