I have tried:
- wiping my outlook configuration and reinstalling my outlook accounts
- taking a brand new machine with Outlook 2010
and it still doesn't work. I now get the error that any communication with the smtp server is interrupted. Apple suport will not help - Outlook is a Microsoft Product but the problem is definately with the server
OUTLOOK DOES NOT WORK WITH OSX Server 10.8
The Apple Mail server has four authentication methodes it can use:
- Digest (CRAM-MD5)
- APOP (POP only)
Microsoft Outlook and Outlook Express can't use CRAM-MD5 authentication. The free Mozilla Thunderbird can. The problem is thus not with Apple, but with Microsoft, although I don't think calling Microsoft will help a bit.
You can lower the Mail Server security by allowing the Cleartext authentication method, use Kerberos (better) or limit yourself to POP mail if you wish to use Microsoft products to connect to the Apple Mail server.
I have already doen all of those:
Authentication is by 'Any Method' - all four options ticked in Server app and I am trying to get a POP3 connection. Whne I test from Outlook it initally shows the POP3 connection to be okay before failing on the SMTP connection and returning:
SMTP log on the server shows:
Oct 10 17:16:56 miniserver.sedgewick.org log: auth: Error: od(nickgray,192.168.1.21): Authentication server failed to complete the requested operation.
Oct 10 17:16:56 miniserver.sedgewick.org log: auth: Error: od(nickgray,192.168.1.21): authentication failed for user=nickgray, method=DIGEST-MD5
Oct 10 17:17:02 miniserver.sedgewick.org log: pop3-login: Login: user=<nickgray>, method=PLAIN, rip=192.168.1.21, lip=192.168.1.3, mpid=13864, TLS
Oct 10 17:17:02 miniserver.sedgewick.org log: pop3(pid 13864 user nickgray): Disconnected: Logged out top=0/0, retr=0/0, del=0/54642, size=5472292395
192.168.1.21 is the static IP address of the machine running the Outlook client
Sorry that is from the mail server log
The SMTP log has:
Oct 10 17:17:02 miniserver.sedgewick.org postfix/postscreen: CONNECT from [192.168.1.21]:55471 to [192.168.1.3]:25
Oct 10 17:17:02 miniserver.sedgewick.org postfix/postscreen: PASS OLD [192.168.1.21]:55471
Oct 10 17:17:02 miniserver.sedgewick.org postfix/smtpd: connect from unknown[192.168.1.21]
Oct 10 17:17:02 miniserver.sedgewick.org postfix/smtpd: error: validate response: error: Authentication server failed to complete the requested operation.
Oct 10 17:17:02 miniserver.sedgewick.org postfix/smtpd: error: validate response: authentication failed for user=nickgray (method=DIGEST-MD5)
Oct 10 17:17:02 miniserver.sedgewick.org postfix/master: warning: process /usr/libexec/postfix/smtpd pid 13890 killed by signal 6
I have now explicitly set the authentiaction method instead of using "Auto" on the Outlook client and I am new back to relay access denied - one step forward = one step back
SMTP log on the server shows:
Oct 10 17:34:37 miniserver.sedgewick.org postfix/smtpd: NOQUEUE: reject: RCPT from unknown[192.168.1.21]: 554 5.7.1 <nckgry<at>gmail.com>: Relay access denied; from=<nick<at>nickgray.org> to=<nckgry<at>gmail.com> proto=ESMTP helo=<QuadCore>
Oct 10 17:34:38 miniserver.sedgewick.org postfix/postscreen: PASS NEW [126.96.36.199]:38754
Mark - thank you for your help with this. As my earlier posts suggested my patience had run out with this new Mini server. Having invested 3 days so far to get it working with all my iOS and mail.app clients this is pretty frustrating
I checked that earlier - they were imported from 10.6.8 - SLS
primary zone: miniserver.sedgewick.org - machine,nameserver and mail exchanger
If there was an error here I would expect the iOS and mail.app clients on the LAN not to work - but they do
I am currently looking at permitted networks:
On the (very reliable but now broken) SLS server I had added 'Accept SMTP relays only from these hots and networks" and added the LAN address range 192.168 etc
This option is gone on MLS but I see in serveradmin settings mail that there is a command mail:postfix:mynetworks:_array_index:0 = 127.0.0.0/8 - Do you know of a way to add mail:postfix:mynetworks:_array_index:1 = 192.168etc?
The Server app rountinely adds variables to the array but I cannot see how to do it from the command line - I can edit existing lines using serveradmin settings mail:etc but not add. I am loathe totry and find the config file and edit as MLS seems to destroy and recreate these at every opportunity
My best guess so far....