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sounds like you're planning on committing an egregious match violation
Applying to a different specialty!
It's a bit more complicated than above.
Technically, it's a match violation to look for a concurrent position if you've already matched to a position. You're supposed to get the waiver first, then look for a new position. In fact, PD's are encouraged to check the NRMP status of all of their applicants prior to offering interviews. But I expect that few do.
But, you're probably thinking that you'd rather apply for something new, see what happens, and then decide on resigning.
Here's what I'd suggest: Apply to your new specialty in September. By November, you'll have a good sense of your interview offers. If you have lots of interviews and you plan on trying to match again, resign in November -- this ensures that your current matched advanced program has plenty of time to interview for that spot in the match. Waiting until January doesn't really help you at all, and actually going on interviews while matched is certainly a match violation. Remember that if your current matched program were to make a stink about it, you could be found to be a match violator and lose all of your matches.