What are the best options for extending my stay in Thailand after using multiple visa exemptions?

Now as far as flying out and then crossing by land to get back in, I'd say there's TWO places you could cross pretty trouble free,

One would be to fly to Vientiane Lao and cross by land at the Nong Khai border crossing (hands down the easiest border IN thailand to get in from)

Another one would be fly to Penang Malaysia and cross by land at the Sadao border crossing (not as easy but not a tough border to get in at)

Suggest you read this post of

@Tod ********

about the border bounce...

4/?mibextid=Nif5oz

𝗗𝗼 𝗜 𝗿𝗶𝘀𝗸 𝗯𝗲𝗶𝗻𝗴 𝗻𝗼𝘁 𝗹𝗲𝘁 𝗯𝗮𝗰𝗸 𝗶𝗻 𝗶𝗳 𝗜 𝗱𝗼 𝘃𝗶𝘀𝗮 𝗿𝘂𝗻?

That is between you and the officer you face at passport control when you stamp back into the country. There's not a person on this group who can answer that question with any degree of accuracy. It's a total crap shoot.

With that being said, if you haven't used your two free land entries and use a service to get you out and back you should be fine (trying to save a satang or three and bounce yourself COULD end up costing you more if you pick the wrong place to bounce at)

Even getting a tourist visa from a thai consulate is no guarantee you get back into thailand, only that IF they let you in you get in for 60 days, <- but getting a tourist visa at a nearby consulate and then entering by land has low exposure to having any issues entering

I think you need to understand the difference between two things

𝗩𝗜𝗦𝗔 𝗥𝗨𝗡 - is where you RUN to a thai consulate in another country and BUY a visa

𝗕𝗢𝗥𝗗𝗘𝗥 𝗕𝗢𝗨𝗡𝗖𝗘 - is where you go to the border stamp out of thailand BOUNCE in-n-out of another country and back into thailand <- which you can do by air or land..

THESE are the common found requirements for the 30 days extension of stay at your local Thai immigration office. Be sure to have a TM30 address registration on file with them.

And I suggest you ask an experienced border run service company to take you to the Thai border and re-enter the same day.

Ask your local expat groups for their recommended border run service company.

Yes...Get the 30 day extension of stay at your local Thai Immigration office for 1900 Thai baht.

THEN if you want to Stay longer...

DO a land BORDER BOUNCE...

Gets you 30 days stamp as Visa Exempt

And one 30 Day extension of stay.

You can do a maximum of 2 LAND BORDER BOUNCE entries into Thailand EACH CALENDAR YEAR.

DO NOT 🚫 fly into Thailand...

You are at risk of being questioned by Thai Immigration Officers upon arrival and DENIED entry.

Bottom line... you're on thin ice with your many entries into Thailand... Suggest you have a Plan B for the next time you try to Enter Thailand by air.

You might as well apply for the 30 day extension on this entry.

You're allowed TWO free 30 day visa exempt entries by land in a calendar year. So if you haven't taken both of those yet, you could contract with a service provider to bounce out/back and get a new 30 day visa exempt entry after this 30 day extension runs down.

OR

You could slog to a thai consulate in a nearby country and BUY a single entry tourist visa which would stamp you in for 60 days