From what I've learned on the Dis, if you want to "keep" any discount you got on the ticket you'll be upgrading, you have to use it first.
So take your discount ticket, go through the gates, and that "sets" the NEW, non-discounted price onto the ticket. And then you upgrade, which saves you money if your ticket was discounted.
An example using pretend numbers.
Normal 10 day ticket = 300
Discounted 10 day ticket = 290
AP = 400
If you upgrade it BEFORE using it, you will lose that discount, and you'll pay the 110 difference between 400 and 290.
If you use it first, your ticket value resets to 300, so you only have to pay the 100 difference between 300 and 400.
(note: this does NOT work at DLR)
If you're on the Dis, on the theme parks forum there's a "sticky" all about tickets, prices, and upgrading, written by a person who is a moderator there and Cast Member who deals with tickets all day.
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