OS X Server 3.0.1 bug sending email from outlook 2010

Question

Level 1

8 points

OS X Server 3.0.1 bug sending email from outlook 2010

Although I use Apple Mail 90% of the time I run outlook in a vm (I have my reasons).

I can receive email in outlook without any probelms.

When I attempt to send email I get an error

SMTP, server response: "504 5.5.2 < hostname > : Helo command rejected: need fully qualified host name", port: 25, secure (SSL): no, server error: 504, error number: 0x800CCC79.

I found this which helped me fix the probelm...

http://support.apple.com/kb/TS3023?viewlocale=en_US&locale=en_US

Basiclaly the procedure to fix is...

Open terminal server from OSX
sudo nano /Library/Server/Mail/Config/postfix/main.cf
Cursor down to the very bottom of the file
Find line smtpd_helo_restrictions and remove reject_non_fqdn_helo_hostname
To save hold down Ctrl + O (To write file out) the Ctrl + x to exit
IMPORTANT - RESTART MAIL SERVICE FOR CHANGES TO TAKE EFFECT

The trouble is I have now had to do this FIVE times as it keeps reverting back.

Any ideas how I can fix this permantly please?

Is there perhaps something I can do with my MX record to make the helo command bounce as expected?

Thanks

Paul.

Mac Pro, Mac OS X (10.6.8)

Posted on Nov 22, 2013 5:34 AM

Reply

Answer 1

Best reply

cjmandrake

Level 1

40 points

Nov 22, 2013 10:39 PM in response to no2b4go10

Instead of removing that portion of the line I added rules to it to accomplish the same thing. Mine was always changing back before I did this, and since this changed the file has remained the same. This is how my line looks now.

smtpd_helo_restrictions = permit_mynetworks permit_sasl_authenticated reject_non_fqdn_helo_hostname reject_invalid_helo_hostname

All on one line, no wrapping, and in that order. The smtpd process goes through the rules in order, and if they are on your network OR they are sasl authenticated, they can send mail from Outlook clients. This does mean that they have to set up their clients to log in with username and password for the smtp server, which is a more secure anyway.

-Cameron

Reply

Answer 2

Nov 23, 2013 6:34 AM in response to no2b4go10

Microsoft Outlook has been a longstanding issue with this behavior.

As for changing the settings, here's how I usually do this. The postconf -e command shown over in that earlier thread will likely require tweaking as Mavericks has moved the configuration file. You'll need to add the -c switch with the current configuration file location to the postconf command, as Server.app has stashed away its own copy of this file.

sudo postconf -n -c /Library/Server/Mail/Config/postfix

sudo postconf -c /Library/Server/Mail/Config/postfix -e "smtpd_helo_restrictions = permit_sasl_authenticated reject_invalid_helo_hostname reject_non_fqdn_helo_hostname"

Which will allow (only) authenticated users to bypass the HELO checks. What's shown here also differs from that earlier thread as I'm not allowing unauthenticated local access here. Then restart the Postfix server with:

sudo postfix reload

I'll report that article to the  hosts.

Reply