Free Dining Ticket Question

[AllThingsFigment]

If I purchase two day park tickets with the free dining package would I be able to upgrade them to the 4 day military park hopper with water parks and more option when we check in at the resort? Has anyone done this or have experience with it? When I was speaking to a cm they told me that as long as the ticket with the package is less I can upgrade to a higher priced ticket including the military ones as long as the cost of the new ticket is higher. I was surprised when I heard this because I thought that would be considered a discount which you aren't able to combine. I didn't think to ask the cm about it being a double discount until after I had already hung up.

If this is doable then it makes more sense for us to do free dining if its offered however if its not then we are better off going with the military specials for the room. I would prefer to do the free dining so I have everything together in one package but I'm nervous we would get there only to find out we have to upgrade at the regular ticket prices rather then the military one.

Thanks in advance for any info or thoughts!