Eric,
I think adding 465 as you state would be a good addition.

In addition, are there clear instructions in the wiki for adding TLS only
sessions to 587?  Or did I misunderstand and that capability is not yet
enabled in the qmailtoaster suite?

Helmut

-----Original Message-----
From: Eric Shubert [mailto:[email protected]] 
Sent: Friday, January 20, 2012 1:55 PM
To: [email protected]
Subject: [qmailtoaster] Re: how to SMTPS submission/port 587

This is an interesting aspect of email history, and has been clouded 
with confusion for quite some time. I'd like to comment on a few things 
here.

On 01/20/2012 11:20 AM, Dan McAllister wrote:
> Eric, et. al:
>
> The same *qmail-smtp* program (different instances) listens on all 3
> ports (if you have them configured) - the controlling "features" are:
> 1) the port number listed on the exec line (25, 587, & 465 are the most
> common)
> 2) the status of the REQUIRE_AUTH environment variable (undef or 0 means
> auth is allowed - it's always allowed - but, NOT required, 1 means auth
> will be required)
> 3) the status of the SMTPS environment variable (undef or 0 means SSL is
> allowed - it's always allowed - but NOT required, 1 means SSL will be
> required)

Thanks for putting this succinctly. This deserves to be on the wiki if 
it's not.

> NOTE: To get around some ISP's blocking of port 25, some sites actually
> use port 26 (an unassigned well-known-port) as an "alternate" SMTP port
> - this would be implemented in the QMT exactly as these other ports are
> added, except using the different port number.

That's news to me, and nice to know. I typically use another unused port 
as well, but instead of creating a new qmail-smtp instance, have a 
firewall redirect that ports' traffic to port 25. I think this method is 
simpler and leaner.

> As I mentioned in my hotwo a moment ago, the ports each have a
> "standard" way they're supposed to work:
> SMTP (25):
> Auth = allowed (not required)
> SSL = allowed (not required)
> SUBMISSION (587):
> Auth = Required
> SSL = allowed (not required)
> SMTPS (465):
> Auth = Required
> SSL = Required

I'm glad you put "standard" in quotes. Conventional would be a good word 
there.

> As to the port 465 being "depreciated"

The word is "deprecated" btw.

> there is a bit of controversy
> over that...

There's no doubt about that. ;)

> originally, 465 was designed to be /the/ SSL port (the same
> way 443 is /the /https port companion to the http port of 80) -- BUT
> they modified the SMTP protocol to /allow /the use of SSL - even on port
> 25, so the NEED for a separate port JUST to support SSL became
> depreciated...

This is the most informative post I found with google just now:
http://forums.contribs.org/index.php/topic,42378.msg199559.html#msg199559
I believe that it is correct that port 465 has never been RFC specified 
(is not a standard), and the IANA has indeed revoked it
(http://www.iana.org/assignments/service-names-port-numbers/service-names-po
rt-numbers.xml).

This is not to say however that port 465 (smtps) is not widely used and 
implemented. Indeed it (still) is.

> however, several ISPs have started moving towards
> REQUIRING their users to use port 465 (and SSL) when sending messages
> from off their networks (e.g.: from mobile devices and laptops that may
> be connected on other WAN service providers). (Verizon has done this in
> some areas, but I don't think all areas yet).

I'm not familiar with what Verizon's doing, but I do know that google 
now requires encryption for submitting emails:
http://support.google.com/mail/bin/answer.py?hl=en&answer=78799
They support ports 465 (SSL) and 587 (TLS). I believe that port 587/TLS 
is preferred (or at least should be, as it *is* standard), and port 
465/SSL is there only for backward compatibility. They do not need port 
465 to enforce encryption, as their port 587 session does not offer 
authentication until STARTTLS has been successfully initiated. This is 
pretty neat, and something that I hope spamdyke might

> The usefulness of port 465 is no longer in providing the only
> SSL-enabled SMTP access anymore -- now its usefulness is in providing
> SSL-ONLY SMTP access... which is exactly how Kalil (and Verizon and I
> myself) tend to use it...

I'm not clear what you mean by SSL-ONLY, unless you're meaning to 
support clients which can do SSL but not TLS (such as Outlook'03). There 
are indeed still clients in use that can do SSL (aka SMTPS) but not TLS.

It would be nice if spamdyke were able to enforce encrypted password 
use, as dovecot does. I don't know if this is in Sam's future changes 
list or not, but we should check and see if this feature can be 
escalated. It would seem to be easy to implement.

I think the BL here is not what's standard or even correct, but what's 
best for QMT. While I believe that port 465 usage deserves to be 
discouraged, it seems to me that QMT would be more robust if it were 
included in the stock package, perhaps with the services for it disabled 
by default. To me this would be a good compromise.

So what do others think about this? Let's hear from you.

-- 
-Eric 'shubes'


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Qmailtoaster is sponsored by Vickers Consulting Group 
(www.vickersconsulting.com)
    Vickers Consulting Group offers Qmailtoaster support and installations.
      If you need professional help with your setup, contact them today!
---------------------------------------------------------------------------------
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