diff --git a/src/wormhole/test/test_cli.py b/src/wormhole/test/test_cli.py
index 3dd23c7..c6ede48 100644
--- a/src/wormhole/test/test_cli.py
+++ b/src/wormhole/test/test_cli.py
@@ -12,7 +12,8 @@ from twisted.internet.defer import gatherResults, inlineCallbacks, returnValue
 from .. import __version__
 from .common import ServerBase, config
 from ..cli import cmd_send, cmd_receive, welcome, cli
-from ..errors import TransferError, WrongPasswordError, WelcomeError
+from ..errors import (TransferError, WrongPasswordError, WelcomeError,
+                      UnsendableFileError)
 from wormhole.server.cmd_server import MyPlugin
 from wormhole.server.cli import server
 
@@ -65,6 +66,24 @@ class OfferData(unittest.TestCase):
         self.assertEqual(fd_to_send.tell(), 0)
         self.assertEqual(fd_to_send.read(), message)
 
+    def test_broken_symlink(self):
+        if not hasattr(os, 'symlink'):
+            raise unittest.SkipTest("host OS does not support symlinks")
+
+        parent_dir = self.mktemp()
+        os.mkdir(parent_dir)
+        send_dir = "dirname"
+        os.mkdir(os.path.join(parent_dir, send_dir))
+        os.symlink('/non/existent/file',
+                   os.path.join(parent_dir, send_dir, 'linky'))
+
+        send_dir_arg = send_dir
+        self.cfg.what = send_dir_arg
+        self.cfg.cwd = parent_dir
+
+        e = self.assertRaises(UnsendableFileError, build_offer, self.cfg)
+        self.assertEqual(str(e), "linky: No such file or directory")
+
     def test_missing_file(self):
         self.cfg.what = filename = "missing"
         send_dir = self.mktemp()