diff --git a/src/wormhole/cli/cmd_send.py b/src/wormhole/cli/cmd_send.py
index 9274de6..bbba2ce 100644
--- a/src/wormhole/cli/cmd_send.py
+++ b/src/wormhole/cli/cmd_send.py
@@ -254,18 +254,28 @@ class Sender:
         # We use realpath() instead of normpath() to locate the actual
         # file/directory, because the path might contain symlinks, and
         # normpath() would collapse those before resolving them.
+        # test_cli.OfferData.test_symlink_collapse tests this.
 
-        # Unfortunately on windows, realpath() is built out of normpath()
-        # because of a no-longer-true belief that windows does not have a
-        # working os.path.islink(): see https://bugs.python.org/issue9949
-        # The consequence is that "wormhole send PATH" might send the wrong
-        # file, if:
+        # Unfortunately on windows, realpath() (on py3) is built out of
+        # normpath() because of a py2-era belief that windows lacks a working
+        # os.path.islink(): see https://bugs.python.org/issue9949 . The
+        # consequence is that "wormhole send PATH" might send the wrong file,
+        # if:
         # * we're running on windows
         # * PATH goes down through a symlink and then up with parent-directory
         #   navigation (".."), then back down again
         # * the back-down-again portion of the path also exists under the
         #   original directory (an error is thrown if not)
 
+        # I'd like to fix this. The core issue is sending directories with a
+        # trailing slash: we need to 1: open the right directory, and 2: strip
+        # the right parent path out of the filenames we get from os.walk(). We
+        # used to use what.rstrip() for this, but bug #251 reported this
+        # failing on windows-with-bash. realpath() works in both those cases,
+        # but fails with the up-down symlinks situation. I think we'll need to
+        # find a third way to strip the trailing slash reliably in all
+        # environments.
+
         what = os.path.realpath(what)
         if not os.path.exists(what):
             raise TransferError("Cannot send: no file/directory named '%s'" %
diff --git a/src/wormhole/test/test_cli.py b/src/wormhole/test/test_cli.py
index 9409838..6b0265c 100644
--- a/src/wormhole/test/test_cli.py
+++ b/src/wormhole/test/test_cli.py
@@ -203,12 +203,6 @@ class OfferData(unittest.TestCase):
     def test_symlink_collapse(self):
         if not hasattr(os, 'symlink'):
             raise unittest.SkipTest("host OS does not support symlinks")
-        if os.name == "nt":
-            # ntpath.py's realpath() is built out of normpath(), and does not
-            # follow symlinks properly, so this test always fails. "wormhole
-            # send PATH" on windows will do the wrong thing. See
-            # https://bugs.python.org/issue9949" for details.
-            raise unittest.SkipTest("host OS has broken os.path.realpath(), see https://bugs.python.org/issue9949")
         # build A/B1, A/B1/D.txt
         # A/B2/C2, A/B2/D.txt
         # symlink A/B1/C1 -> A/B2/C2
@@ -239,6 +233,15 @@ class OfferData(unittest.TestCase):
         d, fd_to_send = build_offer(self.cfg)
         self.assertEqual(d["file"]["filename"], "D.txt")
         self.assertEqual(fd_to_send.read(), b"success")
+    if os.name == "nt":
+        test_symlink_collapse.todo = "host OS has broken os.path.realpath()"
+        # ntpath.py's realpath() is built out of normpath(), and does not
+        # follow symlinks properly, so this test always fails. "wormhole send
+        # PATH" on windows will do the wrong thing. See
+        # https://bugs.python.org/issue9949" for details. I'm making this a
+        # TODO instead of a SKIP because 1: this causes an observable
+        # misbehavior (albeit in rare circumstances), 2: it probably used to
+        # work (sometimes, but not in #251). See cmd_send.py for more notes.
 
 class LocaleFinder:
     def __init__(self):