Can I complete my 90-day report online using my old passport and transfer my Non-O retirement visa to a new passport?

Question 1, can I do the report online using old passport on the above date

-> No, you cannot do it online. You need to go to submit in person at the immigration office.

Update your TM30 with your new passport number first. Bring nee TM30 receipt and both your old and new passports to your local immigration office. Apply for transfer stamps from your old one to new passport, then submit the 90 days report with your new passport.

Attached is the notification for 90 days online system, on the pop-up window that comes when you go to the online system from the link on the website of the Immigration Bureau.

Question 2,I’m due to apply for Non O retirement extension September ( 30 days before expiry at Bangkok) can I transfer visas over to new passport at this visit to the immigration office?

-> You should transfer stamps now so that you can do your coming 90 days report in time.