Since it's just a binary though, I wound up grabbing the OpenSSL from the old box and patching the binary to just point to that instead. Thing runs fine after that.
This is all, of course, still totally stupid - but I did find myself thinking how much worse comparable events in JS have been for me over the years. What would have been easily an entire afternoon ended up taking 15 minutes - and a chunk of that was just double checking commands I'd long forgotten.