Yes, STARTTLS is broken in precisely the way I pointed out.

BUUUUT!

Now imagine that we have a mechanism that allows the mail server to
state 'TLS is always offered'. The problem can be solved.



On Wed, Feb 8, 2012 at 1:12 AM, Martin Rex <[email protected]> wrote:
> Phillip Hallam-Baker wrote:
>>
>> In practice most email that is sent encrypted is encrypted using TLS.
>> If we had an infrastructure that allowed mail servers to know that
>> their corresponding servers required use of TLS, the man in the middle
>> downgrade attack could be defeated.
>
>
> I'm sorry Phillip, but MTA<->MTA delivery with STARTTLS is thoroughly
> broken and effectively unfixable at the moment.
>
> Not only is there no secure algorithm to determine which domains use
> a TLS-enabled mail relay and which do not, but PKIX path validation
> can not be done because plenty of mail relays are using certs that
> do not validate under the (questionable) TLS X.509 PKI used by browsers,
> and server endpoint validation can not be done because exactly noone
> is carrying the Email domains in their SMTP Server certs for which
> these servers are authorized to receive mail, and several SMTP fanciers
> seem to be strongly attached to the idea that matching to the
> *result* of an MX lookup rather than to the EMail target domain
> would make sense security-wise (it doesn't).
>
> And then there are SMTP servers out there (e.g. @gmail.com), that,
> while being issued by a CA that is recognized under TLS X.509 PKI
> of browsers, neither matches the EMail target domain, nor does
> it match the insecure target of the MX record.
>
>
> In theory, DNSSEC could be used to solve several problems (indicating
> that a domain offers STARTTLS *plus* secure identification of acceptable
> MTA servers.  But in the near term I expect a wide adoption of DNSSEC
> not more likely or faster than the wide adoption of IPv6 to solve
> the IPv4 address depletion...
>
>
> -Martin



-- 
Website: http://hallambaker.com/
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