Can I leave Thailand and return on another 60-day tourist visa exemption after extending my current one?

I’m doing exactly what Tod recommended. got my 60 on arrival. Me and my lady are going to Malaysia for five days and 60 upon return.

Yes I’ve just done that 60days the old way visa in the uk, then 30 days immigration Blueport, then five days in Vietnam with another 60 days on return to Thailand

From experience you should report to the immigration office within 24 hours of arriving in the country if you know you are going to extend otherwise you might get fined.

It's totally depend on immigration officers.

I used to do exactly that back in the days before COVID.

But I would fly to either Hanoi or Singapore and get a TR Visa, which I was extending in Thailand for another 30 days.

I finally got sick of all that, and I got myself a retirement visa after I turned 50

As Tod says there’s no official limit entering by visa exempt by air, BUT they will for sure start question you (ask for onward ticket, fund proof, accommodation booking etc), if you keep try entering on visa exempt for multiple times a year. Also it can depend on what passport you hold, prior entry history, which airport (some are more strict than others). Btw langborder runs are generally a “big red flag” for any immigration officer, so don’t have to many of these in your entry history. At the end of the day there’s no fully correct answer, as it is totally up to the single immigration officer that you hand in your passport to 😉

You can leave and come back for another 60 day stay. There is no limit, but an immigration officer is likely to ask why you are using the visa exemption for long periods of time. Usually, 6mths is ok before questions are asked.

No official rule about how many visa exempt entries you can get by air or land,

but

you'll get pulled aside flying in sooner rather than later and asked what you're doing living here on free stamps

You probably wouldn't have a problem bouncing out/back with a service by land to get a new 60 day visa exempt entry though.