Do I need to apply for a new NON-IMM-O visa or can I extend my stay from a visa exemption stamp?

If they won’t re new early you’ll have to start over no big deal as you have the financial requirements

I will relate this story ONLY because I was there and watched it happen.

A good friend of mine has cancer and had to return to the Netherlands to get treatment, BUT

she was leaving 75 days before her current extension was expiring (in bangkok that's a MONTH before the earliest she could apply which is 45 days before).

We had confirmed flights out and back (showing she was not returning until AFTER the extension expired)

They actually had her apply for the extension which they inked in THEN crossed out in pencil AND no one signed it (so it wasn't valid)

Then they had her write a written appeal with the supporting documentation on why she needed the extension so early. It went under review for 3 days and they called her and said it was approved to come out and get the extension "un-cancelled". We showed up, her file was on the officers desk that we had originally dealt with and in 20 minutes it was approved done.. Then we bought her a re-entry permit and she was good to go

I am relating this only to show you're out nothing by TRYING to see if you can get the extension early, I mean the worst they can say is no.. 🙂

How many days before your extension expires are you leaving Thailand? As some offices allow applications up to 45 days out it could be possible to get it done before you depart.

As John mentioned, if your extension renewal time is approaching you could ask to do it early due to your circumstances and if they agree get it inked in and a reentry permit.

There is no extension for retirement "directly" from tourist entry (visa-edxempt or tourist visa). you need to get Non-O based on being over 50 inside (at the local immigration office) or outside (at the embassy/consulate) Thailand as for the first step for your case.

Immigration may also let you renew early if it's not too far in advance and you can show them why you need to.

You could apply for the non-O while you're in your home country and then you'll be able to apply directly for the extension about 2 months after you return.

You will have to start all over with the Non O Visa as a retiree and the One year extension of stay as retired.