Originally Posted by
fumje
I recently had a similar kind of difficulty rebooking (needed to change, so cancelled, went to rebook, used google flights to set routing, but could not get FFC to show up at checkout). What I wound up doing was just booking the new ticket with credit card, then calling up and giving the agent both records to reconstruct on the original ticket and cancel/refund the new one. I think having the new itinerary fully ticketed helped, and overall it did take about half an hour, but it went relatively smoothly. Not ideal having an extra $1.5k on the credit card for a few days, but they took away the pay at airport option so that was all I could see to do.

In your case, if I was getting some something about "illegal" itinerary, I'd have been inclined to say let's leave it alone and then call back to try again — probably a sign the agent / price desk didn't know what they were looking at.
Very similar to my situation. After my phone convo I tried for hours to get the FFC to show up at checkout, no dice. Tried different browsers, the app, browser on phone- nada, just wouldn’t come up.