outlook.office365.com error on Windows 2003

Hi,

 I have  a Windows 2003 server which displays a certificate warning when I visit 

https://outlook.office365.com

 

Looking at the certificate present I receive "graphs.windows.net" with a long list of around 50 SANs (including login.microsoftonline.com), the certificate looks OK, but displays with an error.

 

If I look at the certificate using a Windows 2012 R2 or Windows 10 server I receive a different certificate for the same website.

My 2003 also fails to load the page for http://www.tesco.com and http://www.digicert.com, I've tried enabling and disabling SSL 1.0,2.0,3.0 and TLS 1.0 - this doesn't make a difference. I've also tried clearing the SSL cache, again no luck.

 

The 2003 server has been patched to allow it to process SHA2 certificates

https://blogs.technet.microsoft.com/pki/2010/09/30/sha2-and-windows/

 

Why does the 2003 server receive a different certificate than the 2012 server? Why is the certificate un-trusted? Is it due to the SANs?