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Somewhat unique Visa Situation

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So in my (USA) passport within the last year (in chronological order) I have an expired work visa, 2 expired 30 day toursit stamps, and 1 tourist stamp that is valid until dec 15. 

 

I leave thailand on dec 18 and return on dec 30. I plan to switch to a year long ed visa in January. 

 

So the question is 1. Should I pay the 500 baht a day (i think thats the rule) for a total of 1500 baht (3 days overstay) or should I pay 1900 to extend for 30 days only to stay for 3 extra days? 2. Will I have any trouble getting a 4th 30 day visa stamp  when I come back on dec? 3. Should I pursue the 6 month tourist visa when I'm back in the US instead?

 

Appreciate any productive feedback :)

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It is a bad idea to enter using visa exempt entry following an overstay. Visa exempt entry is already on the radar and the overstay would give extra reason for the IO to scrutinise your history and reason for being in the country. So I would recommend you extend and don't overstay.

It is never a good idea to intentionally break a law, especially when you are guest in the country.

It's not really unique, people have this all the time, personally I wouldn't overstay, just pay the extra 400 Baht and be safer, although the chances of you being picked up for a overstay are slim it does happen

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