Autodiscovery outlook 2016 not working for secondary domain on exchange 2010 sp3 SBS2011.

tmhooft01
tmhooft01 used Ask the Experts™
on
setup:

SBS2011, exchange 2010 with sp3.
internal domain: domain1.local
external domain: domain1.eu
external dns a records
remote.domain1.eu   external ip (godady certificate is on this one)
mail.domain1.eu   external ip
autodiscover.domain1.eu external ip

configuring outlook 2016 with just email address and password works fine.

Now there is a second domain on the same box where autoconfigure does not work all the time
It hangs ons searching email server settings right after a certificate error (which is understandable cause it belong the domain above)

external dns a records
remote.domain2.eu   external ip (godady certificate is on this one)
mail.domain2.eu   external ip
autodiscover.domain2.eu external ip

After writing this question and leaving the search open after 15 minutes plus I do het a user name password question and outlook is configured.
Strange! help much appreciated!

Thanks, Tom.
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Commented:
Run an Outlook Autodiscover ExRCA test at https://testexchangeconnectivity.com.

Run this in a command prompt and let me know the results:

nslookup -q=a test.domain2.eu 8.8.8.8

Author

Commented:
Hello Texas!! Thanks for helping out!

the nslookup for test.domain2.eu fails
nslookup domain2.eu comes back with domain registrars IP

the nslookup for test.domain1.eu comes back with domain registrars IP (different)
nslookup domain1.eu comes back with domain registrars IP

Commented:
Ok I'm trying to establish if there is a wildcard DNS entry which can cause issues for Autodiscover.  When you say it returns the registrar IP, do you mean the A record query for test.domain2.eu was able to resolve a WAN IP?

What about the ExRCA test?
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Author

Commented:
Oh sorry, It did not upload.
It is not resolving to the correct wanIP  where exchange is listening.
I think that is the wildc
But neither is domain1.eu

I changed the record  domain2.eu from the hoster to the external ip the exchange server is listening on.
I'll let you know. Have leave the house in a little bit so please give me some time.
THank you so far! Tom.
autodiscover-test.txt

Commented:
No problem.  Good luck.

Author

Commented:
Hi Jason,

That was it. The discovery works fine now.  Thank you for you help. I am just wondering if there were records I was missing. Any idea?
Thanks again! Tom
Commented:
Generally you need at least two:

Type: A
Host: mail.domain.com
Value: <Insert WAN IP>

Type: CNAME
Host: autodiscover.domain.com
Value: mail.domain.com


Optional:

pop.domain.com
smtp.domain.com
imap.domain.com

You can technically get by with one and avoid the extra expense of a SAN certificate, but for simplicity sake just ensure at a minimum  you have mail and autodiscover.

Author

Commented:
Thank you for your help Jason!

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