diff --git a/src/wormhole/cli/cli.py b/src/wormhole/cli/cli.py
index ba5ec2c..46b6d68 100644
--- a/src/wormhole/cli/cli.py
+++ b/src/wormhole/cli/cli.py
@@ -10,7 +10,7 @@ from . import public_relay
 from .. import __version__
 from ..timing import DebugTiming
 from ..errors import (WrongPasswordError, WelcomeError, KeyFormatError,
-                      TransferError, NoTorError)
+                      TransferError, NoTorError, UnsendableFileError)
 from twisted.internet.defer import inlineCallbacks, maybeDeferred
 from twisted.python.failure import Failure
 from twisted.internet.task import react
@@ -109,7 +109,7 @@ def _dispatch_command(reactor, cfg, command):
         msg = fill("ERROR: " + dedent(e.__doc__))
         print(msg, file=cfg.stderr)
         raise SystemExit(1)
-    except WelcomeError as e:
+    except (WelcomeError, UnsendableFileError) as e:
         msg = fill("ERROR: " + dedent(e.__doc__))
         print(msg, file=cfg.stderr)
         print(six.u(""), file=cfg.stderr)
@@ -173,6 +173,10 @@ TorArgs = _compose(
     "--text", default=None, metavar="MESSAGE",
     help="text message to send, instead of a file. Use '-' to read from stdin.",
 )
+@click.option(
+    "--ignore-unsendable-files", default=False, is_flag=True,
+    help="Don't raise an error if a file can't be read."
+)
 @click.argument("what", required=False)
 @click.pass_obj
 def send(cfg, **kwargs):
diff --git a/src/wormhole/cli/cmd_send.py b/src/wormhole/cli/cmd_send.py
index 307494b..4c96d9b 100644
--- a/src/wormhole/cli/cmd_send.py
+++ b/src/wormhole/cli/cmd_send.py
@@ -6,7 +6,8 @@ from twisted.python import log
 from twisted.protocols import basic
 from twisted.internet import reactor
 from twisted.internet.defer import inlineCallbacks, returnValue
-from ..errors import TransferError, WormholeClosedError, NoTorError
+from ..errors import (TransferError, WormholeClosedError, NoTorError,
+                      UnsendableFileError)
 from wormhole import create, __version__
 from ..transit import TransitSender
 from ..util import dict_to_bytes, bytes_to_dict, bytes_to_hexstr
@@ -274,9 +275,16 @@ class Sender:
                     for fn in files:
                         archivename = os.path.join(*tuple(localpath+[fn]))
                         localfilename = os.path.join(path, fn)
-                        zf.write(localfilename, archivename)
-                        num_bytes += os.stat(localfilename).st_size
-                        num_files += 1
+                        try:
+                            zf.write(localfilename, archivename)
+                            num_bytes += os.stat(localfilename).st_size
+                            num_files += 1
+                        except OSError as e:
+                            errmsg = u"{}: {}".format(fn, e.strerror)
+                            if self._args.ignore_unsendable_files:
+                                print(u"{} (ignoring error)".format(errmsg))
+                            else:
+                                raise UnsendableFileError(errmsg)
             fd_to_send.seek(0,2)
             filesize = fd_to_send.tell()
             fd_to_send.seek(0,0)
diff --git a/src/wormhole/errors.py b/src/wormhole/errors.py
index 06f74d3..7763f73 100644
--- a/src/wormhole/errors.py
+++ b/src/wormhole/errors.py
@@ -3,6 +3,16 @@ from __future__ import unicode_literals
 class WormholeError(Exception):
     """Parent class for all wormhole-related errors"""
 
+class UnsendableFileError(Exception):
+    """
+    A file you wanted to send couldn't be read, maybe because it's not
+    a file, or because it's a symlink that points to something
+    that doesn't exist.
+
+    To ignore this kind of error, you can run wormhole with the
+    --ignore-unsendable-files flag.
+    """
+
 class ServerError(WormholeError):
     """The relay server complained about something we did."""