I had an interesting case of this at the SFO 1K Center recently, where I knew that the only way to get something done was to ask and ask and ask (politely, politely, politely):

I had arranged for an SFO-LHR award for a family member, XF going over and XC coming back (WL for XF on the return). I wanted to issue the ticket, so the 1K Desk res agent had noted the record to be OK for split-award ticketing.

I got to the 1K Center at SFO to ticket and the agent, though happy to do the ticket as a split award, didn't know how to do it in the computer (much more complicated than a normal award, evidently). She called a 1K Res Supervisor and asked how to do it-- and was told it's no longer legal and couldn't be done.

If I'd been on the phone, I'd have thanked politely, hung up, and called again-- but I wasn't about to suggest to the 1K Center agent (terrific woman, BTW) that she hang up and try again. So, had to go with a full XF even though seating on the return is XC and the WL isn't likely to clear for XF on the return. Oh well.

Nice side note: I was also purchasing a hefty international ticket for myself for personal travel... I asked if there was any way she could drop the fare a little-- and she offered either a $150 travel cert to use toward it or an international upgrade cert... very nice offer. I went with the travel cert, believe it or not. Ah, hindsight-- should have gone for the cert!!