Viktor Dukhovni <postfix-us...@dukhovni.org> writes:

> On Wed, Oct 02, 2013 at 07:38:42PM -0400, micah wrote:
>
>> I suppose there is no way to achieve some middle ground of doing
>> opportunistic encryption, but for those who are only talking with bad
>> protocols and ciphers (or clear-text) do a non-permanent failure with a
>> message about their bad protocol so at least some admin eventually may
>> see that information (perhaps when the user complains that their
>> messages are slow to be delivered).
>
> What would be the point?  You accept plaintext mail, but reject
> mail encrypted with algorithms vulnerable to a costly, but not
> infeasible brute-force effort?

No, both plaintext and bad crypto would either be soft rejected with
message to give a delay annoyance.

>> > You could disable SSLv3 in the SMTP client, and use only TLSv1,
>> > TLSv1.1 or TLSv1.2.
>> 
>> Do you mean in the MUA, or in the 'smtp' configurations in postfix? If
>> the latter, what happens when you disable SSLv3 and connect to a remote
>> MTA to make a delivery and they do not support anything but SSLv3?
>
> In all SMTP clients, since SMTP servers almost universally support
> TLSv1.  There are exceedingly few servers that don't.  You'd end
> up sending in the clear to these.  Disabling SSLv3 is not very
> useful yet, the benefits only become real when TLS extensions sent
> by the client allow servers to choose more secure parameters for
> EECDH or EDH, which is not possible yet due to API and protocol
> limitations.  This said it is unlikely to cause any significant
> problems.
>
>> > Neither Postfix nor OpenSSL actually care about the size of the
>> > prime in "smtpd_tls_dh1024_param_file".  You can make it 2048 bits,
>> > and likely get away with it.  See recent thread on Exim TLS interop.
>> > YMMV, some clients may choke on 2048-bit EDH (though more typically
>> > these limited implementations are in are browsers, ... not MTAs).
>> 
>> Interesting, what interoperability problems are there here? If you set
>> the smtpd_tls_dh1024_param_file to a 2048bit file, what happens when a
>> client chokes on this? Does it fall back to clear text, or a non-EDH
>> cipher, or does it cause a connection reset... or?
>
> Some clients don't implement EDH for primes larger than some limit,
> possibly as low as 1024 bits.  Such issues are common in browsers,
> and perhaps MUAs, but very uncommon in MTAs.  When the TLS handshake
> fails, the MTA behaviour is implementation dependent.  Postfix (which
> does not have such limits) retries with plaintext, unless constrained
> by out-of-band policy (administrative or DANE).

Thanks for the explanation.

micah

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