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Re: draft-hoffman-rfc2487bis-03.txt
> > A server which does not have a certificate installed and which does not
> > support any anonymous ciphers SHOULD NOT advertise the STARTTLS keyword
> > as it is not currently able to negotiate the use of TLS.
> It's an case which implementors commonly get wrong.
Further, it's also an area where past SMTP proxy servers have made mistakes.
The proxy servers attempt to validate the SMTP commands as a
man-in-the-middle, passing through the STARTTLS option knowing full well
that they won't allow for TLS negotiation anyway. In one particular case,
the proxy server responded "250 OK" to the STARTTLS command (and, in fact,
it responded that way to _any_ unrecognized command) leading to a serious
communications breakdown as the client was starting to negotiate TLS while
the server was happily awaiting its next plain-text command.
--Marc