How can I re-enter the US after time in Canada on the VWP?
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Your ESTA did not expire 90 days after your first trip to the US. This is not how it works, and probably is why you are confused.
The ESTA is good for two years and multiple entries.
Approved ESTA applications are valid for a period of two years, or until the passport expires, whichever comes first, and multiple trips to the United States without the traveler having to re-apply for another ESTA. When traveling to the U.S. with the approved ESTA, you may only stay for up to 90 days at a time - and there should be a reasonable amount of time between visits so that the CBP Officer does not think you are trying to live here. There is no set requirement for how long you must wait between visits.
So, presuming you got it last July, you should be fine to transit the US in December and January.
Now, if you really did get your ESTA two years ago, then it is expired, and you only need to reapply before your next trip.
If you aren't sure, you can check the status of your ESTA at the DHS ESTA website.
(Also note that while Canadian citizens are exempt from ESTA, non-citizen Canadian residents are not. So it's irrelevant that you are studying in Canada; your Australian citizenship applies.)
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