Mail Tips not working inside after new SSL cert.

What version of Exchange? If its 2007-2013 then what is the EWS URL?

It is very possible that you are having an issue connect into the EWS internal URL due to the lack of an SSL certificate for the namespace, which is causing the issue. Can you create a self signed one or something from an internal PKI to assign to this server?

Exchange 2010. I was thinking a long the same lines.  The server host name is husky on the inside and the outside (also bound as primary on the SSL cert).  Using the same name inside and outside is something I usually say away from, but this is something that I inherited.

Sounds like you need to reconfigure your Internal Exchange URLs to match your External Exchange URLs. Then configure split-brain DNS.

Step by step instructions and lots of screenshots are here.
http://supertekboy.com/2014/05/27/designing-a-simple-name-space-for-exchange-2010/

Everything you need to know! :)

Yup, thats basically it. You would need to create a forward lookup zone and then point those A records to your CAS / CAS Array. afterwards reconfigure the InternalURL to match the ExternalURL across all Client Access services.

Good article btw pal.

I wish it was that easy. I am already running split DNS, I had to setup split DNS 2 years ago when I first start as the exchange server was have issues with OOF and Calendaring assist.  The strange part is that OOF and Calendaring assist are still working.  Note, it's a single CAS. Thanks for trying.

If you already have split DNS, then you just need to reconfigure paste the contents of each external URL over each internal URL. I go into many environments where split-brain DNS has already been configured and do this.

I am sorry, I guess I did not clarify myself. This has been done, both split DNS and the changes to the internalURL and externalURL have been made.  I have also reboot the server twice.  A went as far as creating a CNAME for autodiscover  and creating a _autodiscover service record with my DNS point to autodiscover.mydomain.com

hrm. what happens if you do this with outlook closes (run this from a command prompt):

Outlook.exe /cleanmailtipcache

Select allOpen in new window

I would try this after you confirmed that AutoD is working properly with those new DNS records, as that sounds like the issue.

Tried it from a more terminal server, no dice.  Thanks for the idea.  Autod is working correctly because I can setup a new outlook client and it finds exchange with out issues.  Plus running the outlook autodiscover test works great.
Thanks again for the ideas.
Bill

Hrm.. I dunno then, do you get an error doing a mailtip lookup within Outlook, or do you see anything within the CAS Event Viewer: Application logs?

I am sorry, I guess I did not clarify myself. This has been done, both split DNS and the changes to the internalURL and externalURL have been made.  I have also reboot the server twice.  A went as far as creating a CNAME for autodiscover  and creating a _autodiscover service record with my DNS point to autodiscover.mydomain.com

Ok. So you changed all 6 internal URLs?

Yes, I changed all 8 (6 in GUI and 2 from powershell (EWS)), I am still think the problem is the server having the same host name but not the same domain, IE local vs com.

Mailtips comes from the availability service, therefore you need to look at what is being returned to Outlook by Autodiscover. I have seen things not work as expected even after changing the URLS. For example a mistake I used to make often was setting the URL for EWS wrong, and making is asp instead of asmx at the end.

Use the test email autoconfiguration tool in Outlook to check. Right click on the Outlook icon in the system tray while holding down ctrl to get the option.

Simon.

Simon,
Thanks but I have already done that. Autodiscover works perfectly.

Thanks,

Bill