Upgraded to Exchange 2010 now outlook 2013 can't connect externally

Outlook 2013 used to connect to my exchange server via our TMG before upgrading to 2010. At first the clients were changed back to NTLM all the time but I fixed that and we now see basic with SSL. Now we get repeated logon.
I have used rpc connectivity analyser and it tells me that my (self issued) certificate doesn't chain properly - but the signing certificate is loaded on the client (by Enterprise CA policy) and looking at the mail server certificate in the certificate manger
reports the certificate to be good and correctly shows the chain (so is this a problem in the anyalyzer or does outlook constrcut its certificate chain using a different code library than say IE?).
Oddly Windows 8.1's mail cient works flawlessly when outlook 2013 goes into loops?
Any suggestions?
ICHC

Hi ICHC,
Just as Ed said, we should create new rule on TMG during the upgrading. 
Found an blog for your reference:
Upgrade from Exchange 2007 to Exchange 2010 - Part II
https://www.simple-talk.com/sysadmin/exchange/upgrade-from-exchange-2007-to-exchange-2010---part-ii/
Disclaimer:
Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software of information found there. Please make sure
that you completely understand the risk before retrieving any suggestions from the above link.
Thanks
Mavis
Mavis Huang
TechNet Community Support

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