What are the risks of entering Thailand multiple times on a 30-day visa exemption?

We came into BKK last week with METV that we got in NYC. The IO asked me why we got METV? I said because we were planning to stay for 3 months, but would be traveling in and out to neighboring countries during that time. He said “with American passport you could just get 30 day visa exempt each time.”

3 entry in six months limit - is six months. The number of entries and duration of stay is determined by nationality. This is the first I have heard of a limit for fly ins.

If there are 10,000 tourist who enter Thailand in 1 day and 10 have issues at the point-of-entry, do all tourist have issues at the point-of-entry? We only hear about the 10 and assume it's the 10,000.

I have not once had issues at the airport or land crossing. I have been a habitual tourist for the past 5 years.

Sure I am lucky but also, I am polite, respectful and prepared.

Garrett is incorrect once again, please stop minimalizing what's going on. Yes, you're at risk of being denied and probably will be harassed at the very least, that's where things are at currently with the airports. If you say it's a business trip that can make them ask why you don't have a business visa or work permit etc.

I would not say you are risk free, particularly if you are travelling for business to your company's head office. Certain types of business activities are since 2015 not considered "work" and don't need a work permit but this is from the department of labour point of view rather than immigration.

Many think this logically implies attending a meeting should also be allowed on a visa exempt entry from an immigration point of view (and that is the common practice, and always had been even before 2015- when there was no hassle over air visa exempt entries anyway). But it is a grey area and there are legal opinions to the contrary (see below).

The safest way to proceed would be to get a non-immigrant business visa. You'll probably be OK with a visa exempt but frequent travellers into Bangkok by air do have a risk of questioning and denial. I wouldn't mention that you are coming to visit your company to immigration. Again, that could be OK, or it could be not- depending on the specific IO.

/18/thai-law-foreigners-need-business-visas-to-attend-meetings/

The 2 times a year is for land only. I have only entered Thailand 1 time this year by air but I am sure I would get grilled in DMK and Phuket.