> Matus UHLAR - fantomas wrote:
> >> On Mon, 4 May 2009, LuKreme wrote:
> >>> This is what port 587 is *for*. This is what SASL authentication is *for*.
> > 
> > On 05.05.09 09:25, Charles Gregory wrote:
> >> Hmmmm. Quick (dumb) question. If I tell my users to click the little 
> >> check box in a mail client (Outlook Express or Thunderbird) that says 
> >> "use SMTP authentication", does it automatically switch to port 587, or 
> >> do I need to tell my users how/where to change the port number?
> > 
> > you need the latter.
> > Outlook users may want to use port 465 with non-negotiated SSL.

On 05.05.09 10:45, Adam Katz wrote:
> Funny thing about that; 465 is a non-standard SSL-requiring port for
> SMTP, chosen by Microsoft.  Despite that, Micorosft Outlook (2003+ at
> least) does *not* change the port from 25 when you specify SSL while
> Mozilla Thunderbird will change it to 465.  No configuration on either
> will use 587.

That's because M$ Outlook supports negotiating TLS only on port 25.
On any other port it only supports SSL (non-negotiated) or plaintect. That's
why I recommend (and we do) support port 465.

(I don't remember which outlook version I've been testing, but I remember
the result).

I don't have ay informations that it's microsoft who selected 465 for
smtps, but that's not issue since it looks being widely accepted...

> The official recommendation is to require port 587 and require
> authentication over TLS, but until programs default to using it in
> some capacity, it just seems like a bad idea:
> 
> Users are not smart.  Give them the simplest options.
> 
> Use different servers for MX vs outbound SMTP, and for the latter,
> implement all three ports (25 and 587 requiring STARTTLS and
> authentication, 465 being SSL-wrapped and requiring authentication).

We do that. However, we plan to migrate all users to 587/465 to prevent from
problems if anyone would block 25 (and so we could do that if anything
happens, some users don't need/have to delive mail directly)
 
> If you open SMTP like that, you should probably also have something
> connected to your firewall (e.g. fail2ban for Linux) that will drop
> all connections to mail relays that stubbornly try to connect, or at
> least have the SMTP server configured to do something similar.

I haven't noticed any such problem.
-- 
Matus UHLAR - fantomas, uh...@fantomas.sk ; http://www.fantomas.sk/
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