If I book now and free dining is offered ...

Short answer: Maybe.

If your current reservation is eligible then yes otherwise you'd have to cancel and rebook a new reservation.

If free dining is going to make or break your trip then I'd wait to see if its released and book then.
 


NOV or DEC
Well free dining is usually released the last week in April so that would still give you 180+ days to plan.
Travel dates for November are extremely limited in recent years usually just a few days toward the end of the month and in December it will be around the 6th to 22nd if you base it on this years dates.
 
It just seems to be released so last minute and I like having my reservations in place!
You don't even need a resort reservation to make ADRs. But I agree with the above poster - even April to August isn't last minute, never mind the seven or eight month spread.
 


October has been eliminated most of the time, too. If you book a stay ahead of time hoping they will add the free dining, you might have eliminated your resort by already having a reservation. They base the resorts and number of rooms in the offer to what hasn't been reserved. Free dining is just a way to fill up rooms when there are more vacant rooms. Not all resort and all the rooms at that resort are eligible for the free dining plan.
 

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