Outlook hangs on sending

Hi,

I searched the threads for some similar problem, but couldn't find any.

When trying to send mail using Outlook, the mail basically hangs in the sending folder. Prior to that, a certificate verification is required, but after that, the email doesn't get through. Receiving is ok, IMAP and POP. However, the Test Account Parameter feature (in the Account settings Wizard) does connect to the SMTP and does the full verification process without a single problem...

I'm certain it's a matter of properly configurate the SMTP server settings on the Outlook client (in particular the authentification params), but tried most options available without success. What is strange is that yesterday, it would function properly, with an occasionnal outbound problem like the one descibed here. Now, it's every outbound mail that cannot be processed.

I installed Thunderbird to check if the server config + local and remote firewall rules were ok. Used TLS authentication (if available) for SMTP (SSL doesn't seem to work) and SSL for IMAP and POP: worked like a charm. I cannot replicate this config in Outlook (no TLS on SMTP).

Thanks for your input.

F.

Any clues in /var/log/zimbra.log when you send with Outlook?

Hi Kevin,

Just tried sending something. Here's a snippet of the log:

Code:

---

May 11 11:56:03 philanth zimbramon[24747]: 24747:info: 2006-05-11 11:56:01, STATUS: philanth.clusterspan.net: spell: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: antispam: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: antivirus: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: ldap: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: logger: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: mailbox: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: mta: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: snmp: Running
May 11 11:58:03 philanth zimbramon[25131]: 25131:info: 2006-05-11 11:58:01, STATUS: philanth.clusterspan.net: spell: Running
May 11 12:00:01 philanth zimbramon[25626]: 25626:info: 2006-05-11 12:00:01, QUEUE: 3 1

---

I don't see much in there to make me smile (like an error), but what about the QUEUE line? There would be an email in the message Queue? Unfortunatly, I can't access at the present time the Queue manager (http://www.zimbra.com/forums/showthr...7054#post17054)

Regards,

François

Ok: More with this situation, as it happens.

Without any modification, I can now send emails through the smtp using Outlook. It just decided to do so.

I set up two Accounts in Outlook: one IMAP and one POP.

When I use the POP account, mail goes through the smtp, as described.

When I use the IMAP account, mail just sits there in the outgoing mail folder.

SMTP config for both accounts are EXACTLY the same, except of course for the ports: 993 for IMAP and 995 for POP. The only difference, and not relevant for the smtp (or at least I think so).

Thunderbird is still solid and sends messages with both configs (IMAP and POP, which share a single SMTP config).

Outlook is not my friend anymore, because it died suddenly. Please send flowers to the deceased software.

I still need to be able to send reliably mails through it though: our clients are 95% Outlook lovers, and they don't care so much if Outlook is dead or not :) .

François

what happens when you click send/receive in the imap account?

Hi sam,

Steps:

Selecting IMAP account as Account in the create mail form;

Choosing an arbitrary mail address (outside of the mail server realm);

Clicking Send;

The message is in the outgoing folder forever, in bold italics (not sent at any point in time), with this message: Processing (Status Window);

An error message is written after a little while in the Status Window (roughlly translated from French):

Code:

---

The task «IMAP mail.philanth.clusterspan.net - Send»
has reported an error (0x800CCC7D) : «The outgoing server
(SMTP) does not support secure SSL connexions.  If you could in the past
make SSL secure connections, contact the server administrator or your
ISP».

---

The same error message is displayed every two minutes, the time I set for mail retrieve frequency.

I was indeed able to make a SSL secure connection in the past (yesterday, when I installed Zimbra on the remote server), and now, since Noon (no configs made, no action taken: the SMTP-POP account suddenly lived), but only using the POP account (with the exact same settings as the IMAP account).

I really appreciate your help and concern.

Regards,

François

you can enable logging in outlook to get more information about what its trying to do (in outlook 2003 sp1 or greater only)

tools->options->other->advanced options->enable logging

more infomation about this here:

http://office.microsoft.com/en-us/as...742661033.aspx

let us know if you find anything interesting in the log files.

Thanks for the tip: very precious functionnality I wasn't aware of.

I think Outlook was afraid of your surgical skills, as in ability to dissect its inner workings: as soon as I set up the logs, closed Outlook and reopened it, the IMAP - SMTP just started working again!! Good gracious... Tested again: works all the time.

If ever it starts acting up on me again (and it will), I'll post relevant logs. It just might do the trick again.

Thanks much.

François

Hi,

Outlook started acting up again with the same symptoms this very morning, but I think I found a few clues about the problem.

I should have stated yesterday (my mistake) that I configured Postfix to listen on submission port 587, to get around ISPs that preclude the use of port 25, wanting to set up SMTP to be reachable anywhere and everywhere without changes in the client settings at each new location (hotspots, hotels, etc.).

Thunderbird handles very well TLS AUTH on any port you ask him to connect to. Outlook, the fickle software from a company you might have heard of, doesn't handle TLS very well on other ports than 25 (I'm not even sure it can do that reliably). From my experience now, and from multiple postings on the usenet and the web at large, I can see I'm not the only one to have encountered the problem.

Two questions to any experts out there:

a) I would certainly like to set up Zimbra to handle SSL or TLS transactions on other ports than 25. Would it be advisable to setup Postfix to handle port 465 (SSL) for Outlook, and 587 (TLS) for other more reliable clients?

b) Can I set up SSL on 465 with Zimbra (I would settle on that single port if it's possible)? I see in the admin console that there is a checkbox "TLS only". Does that mean that if I uncheck it SSL might be available, or does it just turn off all types of encryption?

Kind regards,

François

Uncomment these lines in /opt/zimbra/postfix/conf/master.cf:

#smtps inet n - n - - smtpd
# -o smtpd_tls_wrappermode=yes -o smtpd_sasl_auth_enable=yes

and restart postfix. You'll lose this on upgrade.