I agree with Heikki. The user should at least be warned if the server does not support TLS and be prompted
to agree to proceed with a non-encrypted session. The prompt should also have an option to turn of the encryption warning
for any future sessions with that server.


Brian Kirsch - Email Framework Engineer
Open Source Applications Foundation
543 Howard St. 5th Floor
San Francisco, CA 94105
(415) 946-3056
http://www.osafoundation.org



Heikki Toivonen wrote:

RL 'Bob' Morgan wrote:

With STARTTLS, a site like ours that wants to protect people's passwords
can set our IMAP servers to advertise TLS and require that it be
negotiated by a client in order to log in (or they can use
SASL/GSS/Kerberos, but that's another story).  A client that has been
thoughtfully designed will be set to use TLS if it is offered by the
server.  This way the client will work just fine, securely, with our
site *without the user having to configure it*.  And it will still work
fine with plain old sites that just use cleartext.  So everybody wins.
But note this means that the client has to ship with "use TLS if
offered" as a default.  It is sometimes argued that client providers


IMO "Use TLS if available" option sucks. When a user has that set, they
won't know if the traffic is encrypted or not. From usability point it
is great, of course. But from security point of view it would be better
to try and force SSL/TLS and only if that did not work ask the user if
it would be ok to try unencrypted.

--
  Heikki Toivonen

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