It clearly does not like the certificate and you are right with your strategy.  Load the cert locally, then after that, works move to the thumbprint via DHCP/DNS for automation (with blessing of C.O.N.G.R.E.S.S) of course  I still think you need to validate that the cert provided by your network team, is the same one you can see at [URL] If they dont match, you will get the error.  
Hello all!   I'm having a hard time getting my 5030 (fw 5.5.1) to handshake with WMS 3.2.1 44.   I have a certificate installed on both the device and the server and all I'm getting is the message "Idle - Failed to connect due to a certificate issue".  I am unable to get help from professional services because they want an insane amount of money and want to bill my company for 40 hours of work where I'll only need less than one.  Has anyone had experience with setting these devices up?  It's an internally hosted WMS environment.   Thanks in advance!!   Steve Hurd Volta Inc. Louisville, KY
Cannot get 5030 teradici client to handshake w/ WMS