Award and Paid tix on same itinerary
 

I'm planning a trip with my wife. Looking to purchase my ticket with $ and use miles to get an award ticket for my wife. Could we merge our tickets onto the same itinerary (even though she's an X fare class) so that I can clear an upgrade and she can upgrade as my companion?

I tried this recently and the answer I received multiple times was no. You can, however, still upgrade her. It just takes more explanation.