[SOLVED] MailRelay (DynDNS) on Zimbra 6

[mfehr]

I upgraded from Zimbra 5.0.18 to 6.0.0 (Ubuntu 8.04 32 Bit).

The 5.0.18 Zimbra configuration was configured last November and worked fine. As I have a dynamic DNS, I use the DynDNS mailhop service. See Outgoing SMTP Authentication - Zimbra :: Wiki

Since I upgraded to 6.0.0, sending e-mail is no more possible. /var/log/mail.info shows:

to=aaa@bb.com,relay=outbound.mailhop.org[99.999.999.999]:2525, delay=1.1, delays=0.03/0.01/0.96/0.11, dsn=5.0.0, status=bounced (host outbound.mailhop.org[99.999.999.999] said: 550 You must authenticate to use MailHop Outbound (in reply to MAIL FROM command))

The sender receives an error message with the same information. What has changed in 6.0.0?

I noticed that the postmap command behaves differently:

echo outbound.dyndns.org:2525 user@domain.com: password > /opt/zimbra/conf/relay_password
postmap hash:/opt/zimbra/conf/relay_password
postmap -q smtp.gmail.com /opt/zimbra/conf/relay_password

postmap -q returns the username and password in 5.0.18 - in 6.0.0 it returns an empty string. This might be a hint why the mail relay as well does not get a username/password causing the 550 error message

[mfehr]

I found the issue. It seems that the postfix configuration was reset during the upgrade from 5.0.18 to 6.0.0

I checked the configuration of postmap and I found differences between v5 and v6 (Luckily, I run my zimbra server in a VMware instance; I am back on 5.0.18 but am still able to experiment the 6.0.0 upgrade using a different IP address):

postconf ¦ grep smtp_

I had to change the following settings to get it working again:

postconf -e smtp_sasl_security_options=noanonymous
postconf -e smtp_cname_overrides_servername=no
postconf -e smtp_sasl_auth_enable=yes
postconf -e smtp_sasl_password_maps=hash:/opt/zimbra/conf/relay_password

I checked the /var/log/mail.info to see that the message was successfully delivered.

BTW: In my initial message, I mixed up the sample with gmail addresses and the dyndns hostnames. Therefore, I did not get a valid info from postmap. Entering the command with the proper information delivers the expected result... - Sorry for potential confusion.