Greg Troxel <[email protected]> wrote:
> Dmitry Alexandrov <[email protected]> writes:
>
>>> Are you using TLS for SMTP/IMAP?
>>
>> He apparently uses opportunistic encryption (STARTTLS) for some
>> reason.  In such a case a paranoid default behaviour of a server might
>> be understandable (yet not tolerable, if is not optional).
>
> I think it's necessary to separate:
>
>   1) connect and just be unencrypted
>   2) connect, try STARTTLS, and continue on success or failure
>   3) connect, try STARTTLS, and disconnect on failure
>   4) connect via forced-on TLS (a la https)
>
> I don't see that 3 is worse than 4.  1 is obviously bad, and 2 should
> give confidentiality from eavesdroppers but fails with active attackers.
> However, a typical wifi has an active attacker called a captive portal.

You are judging from a client point of view, while we are discussing what is 
reasonable for a _server_.  Their trust has asymmetricity, originating from a 
flaw of centralised trust model of X.509, a flaw not technical but social, yet 
not less fundamental: a client can and normally shall verify server’s public 
key, but the server in practice cannot do the same, because a client typically 
has none.

So all server knows, that there is an encrypted connection.  Whether it came 
from the other end, or from an attacker in the middle, that stripped STARTTLS 
negotiation or even downgraded proper TLS to plain connection, which passed 
unnoticed by a client, that accepts unencrypted connections, — it can only 
guess.  And it _do_ guess basing on a collected knowledge of this very user’s 
habits.

Knowing, that the user _does not use_ proper TLS, and that connection came form 
a place he’d never been before, an overwatchful server suggests the worst.

>> Anyway, you really do not want to use STARTTLS instead of full-plate
>> TLS, if your server supports it (if they are so concerned about
>> security, they ought to).
>
> Why, if the client ... disconnects if TLS is not negotiated?

Because server doesn’t know that, and goes paranoid voiding a password.

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