diff --git a/src/catkin_pkg/workspaces.py b/src/catkin_pkg/workspaces.py
index d6f42730..6eb0e19d 100644
--- a/src/catkin_pkg/workspaces.py
+++ b/src/catkin_pkg/workspaces.py
@@ -92,8 +92,11 @@ def order_paths(paths_to_order, prefix_paths):
 
 
 def _is_equal_or_in_parents(dir_, path):
-    dir_ = os.path.normcase(os.path.realpath(dir_))
-    path = os.path.normcase(os.path.realpath(path))
+    # On Windows, when a symlink points to a path which uses 8.3/short filenames, it doesn't
+    # appear that `os.path.realpath` will resolve both redirections in the same invocation.
+    # We need to work around this non-idempotence by invoking the function twice.
+    dir_ = os.path.normcase(os.path.realpath(os.path.realpath(dir_)))
+    path = os.path.normcase(os.path.realpath(os.path.realpath(path)))
     return path == dir_ or path.startswith(dir_ + os.sep)
 
 
diff --git a/test/test_workspaces.py b/test/test_workspaces.py
index be5a76ad..4729c3de 100644
--- a/test/test_workspaces.py
+++ b/test/test_workspaces.py
@@ -2,6 +2,7 @@
 
 import os
 import shutil
+import sys
 import tempfile
 import unittest
 
@@ -43,6 +44,9 @@ def test_order_paths(self):
         self.assertEqual(['foo' + os.sep + 'bim', 'bar'], order_paths(['bar', 'foo' + os.sep + 'bim'], ['foo']))
 
     def test_order_paths_with_symlink(self):
+        if os.name == 'nt' and sys.version_info < (3, 8):
+            self.skipTest('symlinks are not resolved on Windows prior to Python 3.8')
+
         root_dir = tempfile.mkdtemp()
         try:
             foo = os.path.join(root_dir, 'foo')