I flew to Houston early last year on an ESTA waiver, and upon arrival the officer stamped me in writing B2 on my stamp with 6 months'of validity.
I stayed for one month and then travelled overland to Canada. I border hoped 2 weeks later to get a Canadian work permit and upon entering the U.S. for the hop the officer stamped me again putting 3 month validity.
I then spent six weeks in Canada working before going on a 2 week roadtrip to the U.S., returning to Canada for another month and then, returning once again to the U.S., on the date that the 3 month visa was to expire. I asked the guard what that meant and he just told me according to the 6 month visa I was stamped I was fine, I'm not sure if he knew the rules but by this point I was ultra confused. I was in the U.S. Then up until a week before my 6 month visa expired. I then returned back to Canada and flew home from there.
I just got an email from ESTA saying that my two years is about to expire and I need to apply for a new one. I intend to return to the U.S. in a couple of months so I have a few questions.
Did I actually overstay and if so do I have a valid reason due to the mistakes of officers?
Was my ESTA activated on the date of my arrival in Houston or on the second time I arrived? If the former, would the second officer had stamped the wrong date also?
Would me being a temporary resident in Canada throughout this have any impact?
Do they record all movement between the U.S and Canada electronically? I recall multiple times coming and going and the officers not scanning my passport, only checking it as ID. This would be notable especially on the trip that I returned to the U.S. on the expired date, wouldn't that have flagged them?
Since I flew out of Canada and not the U.S. does that prevent them from knowing my true departure? And if I did get screwed over and get flagged because of all of this, would me flying into Canada and crossing over to the U.S. overland bar me, even though they don't seem to even check the passports there?
This is probably really confusing, it's confusing to me. I thought I was doing the right thing until I read about overstaying ESTA on here.
Edit not from OP (might help but beware, might be wrong):