> Thoughts on how to diagnose the issue?

I would recommend tcpdump on the CAS server to troubleshoot a purely
networking problem. If you see a successful three-way handshake, then
you should look at SSL/TLS issues by performing a Java SSL trace [1].
With one or both of those you should have some evidence to present to
your networking or AD admins.

M

[1] 
https://wiki.jasig.org/display/CASUM/SSL+Troubleshooting+and+Reference+Guide,
"When All Else Fails"

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