smtp authentication does not work with outlook [solved]

mariourk · Last edited by mariourk on Mon Jul 23, 2007 12:52 pm; edited 1 time in total

I have been following this howto to get smtp authentication working with Cyrus-sasl.
This allows me to send emails through my mailserver, even if I'm somewhere else.
The problem is that it doesn't work with outlook. Evolution and Thunderbird go fine,
but outlook refuses to authenticate. I configured the outgoing mail settings in outlook
the authenticate (using TLS) with the smtp-server. But when I try to send an email,
I get a relay access denied error, because outlook does not authenticate.

Does someone have experience with this (very strange) problem?

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magic919 · Posted: Mon Jul 16, 2007 10:22 am Post subject:

Might be worth breaking it down a bit. Can you just smtp-auth without the TLS?

mariourk · Posted: Mon Jul 16, 2007 10:39 am Post subject:

Without TLS, outlook still does't authenticate.
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If there is one thing to learn from history, it's that we usualy don't learn anything from it, at all.

magic919 · Posted: Mon Jul 16, 2007 10:51 am Post subject:

When you telnet to port 25 and give it an EHLO do you get all the smtp-auth options?

schally · Apprentice Joined: 13 May 2004 Posts: 207

mariourk · Posted: Mon Jul 16, 2007 12:35 pm Post subject:

schally · Apprentice Joined: 13 May 2004 Posts: 207

hm,... why you don't make the first step and bann outlock/outlook??
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greetz
- schally

elgato319 · Guru Joined: 15 Sep 2005 Posts: 546

main.cf:
debug_peer_level = 5
debug_peer_list = 10.x.x.x (ip from the outlook client)

if the outlook client connects again you should see more output in your logfiles.

mariourk · Posted: Mon Jul 23, 2007 9:05 am Post subject:

Sorry for the late respons, I've been busy this weekend.

I've used your advise to get some more detailed info from the logs.
There is a difference between outlook and Evolution. But I can't figure out
why there is a difference. Here is the output from the logs.

Download the logfile from outlook here
Download the logfile from Evolution here

I noticed a difference at the beginning of the logs

Outlook

mariourk · Posted: Mon Jul 23, 2007 12:47 pm Post subject:

I think I solved the problem. In outlook I had to enable to use SSL when contacting the SMTP-server.
I tried this before, but that led to another problem. The email returned with this error:

Mr.C. · n00b Joined: 25 Feb 2007 Posts: 35

Make sure that both files listed here:

mariourk · Posted: Tue Jul 24, 2007 9:44 am Post subject:

I will keep an eye on it. Thank you for pointing it out

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If there is one thing to learn from history, it's that we usualy don't learn anything from it, at all.