Free Dining - Adding AP Holder to Room?

[jemrock]

Hello all,

Hoping the Dibb wisdom can steer me in the right path with a couple of questions..we haven't bought annual passes before but with our honeymoon, the 50th anniversary and my 30th all looming within the next few years it might be time to give it a whirl!

So, question one: if I book myself a room when the free dining promotion is next on and meet the qualifications (buy the 14 day ticket from Disney direct etc) so that I have free dining what would happen if I then added my partner (who held an annual pass) to the booking?

Would this

- not be possible without him buying an additional ticket?
-be possible but we would only have one set of free dining credits between us?
-be something else I haven't thought of?

Question two: if we book the room in the usual way and both get free dining but then upgraded to an annual passes during our trip would we lose the dining for the remainder of our stay? I've read you lose fastpasses if you have more than 7 days worth booked so just wondering if it's similar with the dining?

Thank you for any help!