On 2014-08-18 05:03, Gedalya wrote:
On 08/17/2014 10:45 PM, Alex wrote:
Hi,

I have a postfix+dovecot-2.2.13 system and have configured it to support IMAPS on 993 with SSL/TLS. I'm noticing with users using Thunderbird, the
autodetect defaults to IMAPS on 143 with STARTTLS.

Which is preferred? Which is more secure? Which is more common?

Why would someone choose one over the other?

Can I ask the same question about SMTP and submission? Why would one choose
587 with STARTTLS versus 465 with SSL/TLS?

Thanks,
Alex
Implicit SSL ports were specified before STARTTLS was specified,
therefore they are considered deprecated.
There is no major difference between the two in terms of security or
functionality. Ultimately they both just work. And ultimately you
probably want to simply support both for maximum compatibility. (For
older versions of Microsoft Outlook you _must_ support port 465
because they didn't support STARTTLS, although I don't know how many
of these are still out there.)
Technically one can argue that STARTTLS is less secure because it
starts off in plaintext (there even was an exploit recently against
STARTTLS in nginx's SMTP proxy [1]) but that's anecdotal in my
opinion, and the general opinion seems to be in favor of deprecating
993/995/465. A man-in-the-middle can very easily filter out STARTTLS
from the conversation and this would be effective against
_opportunistic_ STARTTLS, but the equivalent of port 993 is a client
that requires STARTTLS and refuses to log in otherwise. From an
admin's point of view, you would prefer to support just one port per
service, and 110/143/25 are the "real" standard ports and people seem
to lean towards that.

Whatever anyone says about this topic will start a flamewar.


[1] http://nginx.org/en/CHANGES-1.6

No need to start a flamewar, I think everything you stated is completely correct. Support everything for maximum compatibility, in fact I seem to recall that iPhone ios mail application doesn't support STARTTLS for imap yet?

From an admins point of view the less ports the better as you say but you will end up with more user confusion and more support requests so the benefit is negated.

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