When Should I Apply for My 90-Day Report After Entering Thailand?

Okay, lets get this sorted out.

The way to tell if the immigration office sync'd your 90 day reporting when you did your yearly extension is to ask yourself

When you got the new year extension did you get a NEW 90 day report receipt from the immigration office stating when your next report was due? if the answer was yes, that new receipt has the date you do your 90 day report on.

IF the answer was NO (and you didn't get a new 90 day report receipt when you got your year extension your 90 day report is due when it always is 89 days from the date you stamped into the country last.

So in the case of the O/P they did NOT get a new 90 day report receipt when they got their year extension granted on Jan 30th. That means that their 90 day report is due 89 days from the date they stamped into the country last which was 19th of Nov.. So the 16th of Feb is the due day.

If you received a new 90days due date slip (additional small piece of paper) on your extension approval, that is it (usually 90days count starts upon application). If you didn't get any paper, 90days is counted from the previous extension means starting your last entry in this case.

And for the clever person who found out that 16 Feb 2020 is on a Sunday, the Thai Immigration is prepared for this.

You make the report between 15 days before till 7 days after due date, in real dates in this case between 1 Feb and 23 Feb and believe me, there are more days the office is open then closed in this 23 day period

What did you have before this extension - when you enter Thailand on November? Non-O visa itself or extension you applied last year?

90 days from the day you entered Thailand

Yes. 16th February

Quickly calculated as you entered on 19 November 2019 using a re-entry permit, 19 Nov plus 90 days makes 16 Feb 2020.