I have always had Clipboard Redirection enabled the whole time. Clipboard Redirection has always worked without problem. CDR is the problem.
Want to throw in my 2 cents and state that I've seen this happen in Application Farms as well. Ranging from Server 2008R2 al the way through 2016.
Have you taken a support bundle? In there should be a file (or files) with a name like 'vmware-TsdrUserServer-<number>'.
you could check that one for errors in copying.
So it turns out we have some security software (unable to disclose) which causes CDR to break on the View Agent side. I deployed the Win10 parent without it and CDR works like a charm. Self-imposed issue. Now we have to get this security software to work with CDR.
Are you able to discuss (offline) the security platform in use?