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Outlook 2016 doesn't update to new server IP address

Posted on 2016-09-19
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Last Modified: 2016-10-18
The public IP address of the Exchange server has changed.
I have updated the Autodiscover DNS record and have waited couple of days for the DNS change to propagate.

After the change, at least one Outlook 2016 client can't connect.  It keeps asking for password and it looks like it has not updated the IP address.

How can I force it to update the IP address?  When I go to 'accounts-> change -> more settings' there are no visible fields for servers' address.
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Question by:ivolach
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Expert Comment

by:Scott C
ID: 41804694
Try the MS Outlook connectivity tester and make sure AutoDiscover is working correctly.

https://testconnectivity.microsoft.com/

Also, you have SBS tagged...what version of SBS are we looking at here?

If it's SBS 2007, then Outlook 2016 isn't a supported client for that version of Exchange.  SBS 2010 should be fine.
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Author Comment

by:ivolach
ID: 41804718
It is SBS2011 hence, Exchange 2010.

The connectivity test is successful, and I have another Outlook 2016 client that has been updated successfully.
The get the successful one working, I had to start/stop few times until a message came up asking if I want to allow the autodiscover to make necessary changes.

Thanks,
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Accepted Solution

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Simon Butler (Sembee) earned 2000 total points
ID: 41805060
Outlook doesn't maintain a list of server IP addresses. It does a DNS lookup.
Therefore forget it is Outlook for a moment. From the machine that doesn't work you should be able to browse to the Outlook Anywhere address - usually https://remote.example.com with SBS 2011 and see the RWW.

If that doesn't work, then the issue is unrelated to Outlook. You then need to do standard troubleshooting for DNS resolution failure. PING and NSLOOKUP to the host name to see if they resolve correctly.

Being picky, there is no such thing as DNS propagation time. The only thing that ever has to propagate is name server changes. DNS changes take time to go live because DNS is cached around the world and that cache has to expire. That is usually 48 hours at most. If you are still seeing old results then it could be that a cache has got stuck, or the workstation has a hosts file on it which is overriding.
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Author Comment

by:ivolach
ID: 41808666
Thanks,
I am waiting for the user to follow the suggestions
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Author Comment

by:ivolach
ID: 41812412
Following testing:
- the connectivity test comes back OK
- Ping and nslookup return different results: the ping returns the right result, the nslookup returns the internal IP for the server rather than the public IP for the remote access.

I have checked the hosts file and there is nothing there.  Tried to add an entry for the public domain with no change in results.  run ipconfig /flushdns, still no change.
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Author Comment

by:ivolach
ID: 41812462
Following a modem reset, nslookup and ping are now resolving to the right IP address.
However, Outlook keeps asking for password, and is not connecting.
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Author Comment

by:ivolach
ID: 41813859
I have tested with 'outlook.exe /rpcdiag' and it looks like outlook is trying to connect to the internal 'server.local' rather than the public 'mail.server.com'
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LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 41814666
That is the expected behaviour.
Outlook will initially try to connect to the server's real name, then failover to the Outlook Anywhere address. Therefore as long as the name doesn't resolve then the client will connect.

You need to ensure that Autodiscover is working correctly, and that the client can indeed resolve the server's external address and connect.
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Author Comment

by:ivolach
ID: 41816231
The client can resolve the server external address and the Autodiscover is working correctly for all other users.
Is there a way to reset the Autodiscover / Outlook anywhere settings just for this user?
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