Kudos to all helping here! I am an American, wife is Filipina, living in Krabi since November 17 under a combination of a 30-day exemption on arrival, 60-day tourist visa obtained after flying to Malaysia, and two 30-day extensions. That is a total of about 5 months. Will it be fairly easy to get another 30 days if we go over the border by land in Malaysia? Also, would we likely be able to extend it for another 30 days, or will that be a problem because it would be going over 6 months within the last 12? Thank you and stay well!
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TLDR : Answer Summary
An American expat in Krabi, who has been in Thailand for about 5 months, is inquiring about obtaining another 30 days upon exiting to Malaysia and the possibility of extending this new entry. Responses suggest that if the expat hasn't utilized two 30-day visa exempt entries by land this year, they should be able to return and receive a new 30-day entry, and extensions may also be feasible.
As long as you don't have TWO 30 day visa exempt entries by land so far this year you should be fine bouncing out and back in to get a new 30 day visa exempt entry.
Keep in mind that SOME borders with Malaysia require you to stay overnight in Malaysia before you can stamp back into thailand.
You should have no problem getting a 30 day extension on a new 30 day visa exempt entry at the immigration office for 1900baht once you get back.
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