Sending from Outlook

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Level 1

12 points

Sending from Outlook

Apologies if this has been asked previously, but I've not been able to find an answer.

I have a client running OS X Server on a Mac Mini Server where every email client I have tried (Mac, iOS, Thunderbird on Windows) is successfully able to send and receive email through the mail server. The notable exception is Outlook (2007 and 2010), where I can't get SMTP to work. It fails with what is clearly an authentication error. I've set it to use TLS and port 587 (which Thunderbird uses and works with) as well as SSL and 465 but with no success.

I'm assuming I'm not the first person to come across this, but I've not found a solution - any assistance would be welcomed.

Thanks,

Des

Posted on Mar 19, 2013 8:03 AM

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Answer 1

bfueler

Level 1

0 points

Apr 9, 2013 5:35 AM in response to ddougan

Did you try this procedure?

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

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Answer 2

ddougan Author

Level 1

12 points

Apr 9, 2013 8:40 AM in response to bfueler

I did - it was nothing to do with that. The problem is to do with the Mail Server authentication settings. I found another thread that helped (https://discussions.apple.com/thread/4164932?answerId=19121632022#19121632022). The resolution is to change authentication from Automatic to Active Directory. Doing that, and then reconfiguring the Mac clients to not use MD5 Challenge Response, resolved the issue.

Des

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Answer 3

UptimeJeff

Level 4

3,479 points

Apr 10, 2013 9:11 PM in response to ddougan

Older versions of outlook pley best with port 465/ssl (not TLS) but you need to enable it in master.cf

Look in:

/Library/Server/Mail/Config/postfix/master.cf

Uncomment these lines:

#465 inet n - n - - smtpd

# -o smtpd_tls_wrappermode=yes

# -o smtpd_sasl_auth_enable=yes

# -o smtpd_client_restrictions=permit_sasl_authenticated,reject

# -o milter_macro_daemon_name=ORIGINATING

Issue

sudo postfix reload

Then retry outlook with port 465/ssl

That should solve it.

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