ESTA return, does the “clock” reset when travelling across Panama - Cuba?

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Since you're reentering after the expiration of your 90-day period, the officer will have to admit you for a new period if you are in fact granted admission. Therefore, you should not need to show that you've been outside North America.

There is some ambiguity in the application of the "contiguous territory" rule, however, so it may nonetheless be helpful to be able to show that you've been to Panama.

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