I looked through the website about AA/Challenges but didn't see anything regarding this. Forgive my ignorance on AA - never done this before.

I had a simple back and forth ORD-TOL-ORD in November on AA and didn't think anything of it. A couple weeks later, did that again. And again. I don't have enough points to make the Gold challenge threshold right now, but I believe that by the end of the second week of January I will.

Couple questions:

--> Can a challenge start/end date cross a calendar year boundary?
--> If yes and I call AAdvantage, will they retroactively start a challenge or would I be at square one when I called?