I would have your colleague ask the support guy to escalate, and do the same thru your sales channel (direct or thru partner). Ask them what they are willing to do if you need a restore tomorrow..... If there clearly isn't any outside factor other than a supported change (OS upgrade) and it broke the solution it's clearly that the person working on your case today isn't capable of or willing to solve the problem. Sounds like the best reason ever for asking for the next level of support.
Side note, sounds nice to log cases by email. They stopped accepting that here this year