diff --git a/_package/tests/unit_tests/filesystem_pyt.py b/_package/tests/unit_tests/filesystem_pyt.py
index 2fc1a3482..7e54a6dff 100644
--- a/_package/tests/unit_tests/filesystem_pyt.py
+++ b/_package/tests/unit_tests/filesystem_pyt.py
@@ -5,8 +5,10 @@
 from pathlib import Path
 import platform
 import shutil
+import sys
 import tempfile
 import unittest
+from unittest import mock
 import uuid
 
 # 2. Third party modules
@@ -261,7 +263,28 @@ def test_is_somewhere_below_system_temp(self):
         """Tests filesystem.is_somewhere_below_system_temp()."""
         temp_dir = tempfile.mkdtemp()
         file_path = _make_bob_file(temp_dir)
-        self.assertTrue(True, is_somewhere_below_system_temp(file_path))
-        self.assertTrue(True, is_somewhere_below_system_temp(Path(file_path)))
+        self.assertTrue(is_somewhere_below_system_temp(file_path))
+        self.assertTrue(is_somewhere_below_system_temp(Path(file_path)))
         Path(file_path).unlink()
         shutil.rmtree(temp_dir)
+
+    @mock.patch('xms.core.filesystem.filesystem.tempfile')
+    def test_is_somewhere_below_system_temp_8dot3_names(self, patched_tempfile):
+        """
+        Tests filesystem.is_somewhere_below_system_temp with a shortened file name on Windows.
+
+        is_somewhere_below_system_temp uses a function internally that returns 8.3 file paths on Windows, which makes
+        people with usernames like LongNameThatExtendsPastThe8Dot3Limit get paths like `c:/users/LONGNA~1/AppData...`.
+        Failure to compensate for that results in callers that pass expanded paths being told their path isn't in the
+        system temp directory, even though it is.
+        """
+        if sys.platform != 'win32':
+            return  # Only Windows uses 8.3 filenames, and this test needs Windows.
+
+        patched_tempfile.gettempdir.return_value = 'c:\\PROGRA~1'
+
+        file_path = 'C:/Program Files/somewhere'
+        self.assertTrue(is_somewhere_below_system_temp(file_path))
+
+        file_path = 'C:/PROGRA~1/somewhere'
+        self.assertTrue(is_somewhere_below_system_temp(file_path))
diff --git a/_package/xms/core/filesystem/filesystem.py b/_package/xms/core/filesystem/filesystem.py
index 042353752..19aa6e451 100644
--- a/_package/xms/core/filesystem/filesystem.py
+++ b/_package/xms/core/filesystem/filesystem.py
@@ -1,4 +1,8 @@
 """Filesystem utility methods."""
+
+__copyright__ = "(C) Copyright Aquaveo 2019"
+__license__ = "All rights reserved"
+
 # 1. Standard python modules
 import os
 from pathlib import Path
@@ -13,10 +17,6 @@
 # 4. Local modules
 
 
-__copyright__ = "(C) Copyright Aquaveo 2019"
-__license__ = "All rights reserved"
-
-
 def clear_folder(folder: str | Path) -> None:
     """Deletes everything in folder.
 
@@ -159,8 +159,8 @@ def is_somewhere_below_system_temp(filename: str | Path) -> bool:
     Returns:
         See description.
     """
-    temp_dir = Path(tempfile.gettempdir())
-    filepath = Path(filename)
+    temp_dir = Path(tempfile.gettempdir()).resolve()
+    filepath = Path(filename).resolve()
     return temp_dir in filepath.parents
 
 
diff --git a/_package/xms/core/time/time_conversion.py b/_package/xms/core/time/time_conversion.py
index 09fb7190c..76aa7bad4 100644
--- a/_package/xms/core/time/time_conversion.py
+++ b/_package/xms/core/time/time_conversion.py
@@ -1,4 +1,8 @@
 """Time conversion methods."""
+
+__copyright__ = "(C) Copyright Aquaveo 2022"
+__license__ = "All rights reserved"
+
 # 1. Standard python modules
 from datetime import datetime
 from typing import Optional
@@ -10,10 +14,6 @@
 # 4. Local modules
 from .. import _xmscore
 
-__copyright__ = "(C) Copyright Aquaveo 2022"
-__license__ = "All rights reserved"
-
-
 time_cpp = _xmscore.time