Three things this month, and all three landed on my desk in the same week. The visa rules just changed, and a lot of you are going to feel it. Retirement in Thailand is becoming more structured, which is good news if you plan and bad news if you improvise. And last month I promised to go deeper on how I actually use AI inside a law firm, so this month I keep that promise.

1. The Tourist Visa Is Back to 30 Days

If you have been living in Thailand on visa-free entries, read this carefully. On 19 May 2026, the Thai Cabinet approved cutting the visa-free stay from 60 days back to 30. This reverses the 60-day exemption that was introduced in July 2024 to boost tourism after the pandemic.

A few details that matter more than the headline:

• You can still apply for a 30-day extension at your local immigration office, so the practical maximum becomes roughly 30 plus 30.
• Visa on Arrival is being cut sharply, from 31 countries down to four (Belarus, Serbia, India, and Azerbaijan).
• A new 15-day visa-free category is being added for Seychelles, Maldives, and Mauritius.
• ASEAN neighbors such as Malaysia, Brunei, Indonesia, and Singapore keep their own arrangements.
• The Thailand Digital Arrival Card (TDAC) is still mandatory before you land. The paper form is gone.

The government is honest about the reason. This is a crackdown on people who use tourist entry to work without a permit, run a business quietly, or operate the call-center scams that have been in the news. Officials also point out that the average tourist stays around nine days, so they argue real tourism is barely affected.

The other half of the story: the border is going digital

The same week the visa was cut, on 29 May 2026, immigration started testing a new official app called THIM (Thailand Immigration Management System), built for the Immigration Bureau with Amazon Web Services and a local partner. It lets you submit your arrival information from your phone before you land, on top of the TDAC arrival card that has been mandatory since May 2025. For now it is a test, with a wider rollout possible from 1 October 2026.

Officials are openly describing it as a future immigration “super app.” The stated goal is to speed up arrivals while tightening security, and the roadmap reportedly includes things like visa extensions and the 90-day report being done from the app instead of in a queue at an office. The deputy immigration commissioner framed it as making the border match a modern, welcoming country.

Here is my read. Put the two announcements side by side. The same government shortening the visa-free window is also building the digital tools to track who stays and what they do once they are here. That is not a contradiction, it is a plan. If you are an actual tourist, all of this is noise. If you have been living in Thailand on back-to-back exemptions and border runs, the door is closing, and it was always going to. The era of treating a tourist stamp as a residence permit is ending. The fix is not to panic, it is to get on the right visa: a Non-O if you are married to a Thai or have a Thai child, and we have a great many clients in exactly that position, a retirement visa if you are 50 or over (see below), the DTV if you work remotely, the LTR if you have the income or assets, or an education visa if you are studying.

Not sure which one fits you? We built a free AI visa finder on our website. Answer a few quick questions and it points you to the visa options that match your situation, before you spend anything on advice.

2. How I Actually Use AI Inside a Law Firm

Last month I promised to go deeper on AI for business and law. Here it is, with no hype and a clear warning at the end.

I was wrong about AI, and I will say it plainly

Two years ago I was convinced AI would replace people (actually many jobs). I was wrong. What I see now is different and more useful. AI makes mistakes and it has to be watched, but a person who uses it well becomes almost superhuman. You work better, faster, and more efficiently than you ever could alone.

Jeff Bezos said something close to this last month. In a CNBC interview he compared handing a worker AI to giving a bulldozer to someone who had been digging with a shovel, and argued that AI will elevate people rather than replace them. I agree with the direction. I would only add the part he skips: the bulldozer still needs a driver who knows what they are doing. Hand it to the wrong person and you get a bigger hole in the wrong place, faster.

The model matters less than you think

AI has evolved enormously in the last year. I stopped using ChatGPT last year because Gemini and Claude were clearly ahead. Last month OpenAI released GPT 5.5 and it does look promising again. But here is the honest truth about new models: each one is a bit like a new iPhone. A better camera, a few nice touches, and on paper it is faster. In daily use, can you really tell? The question is not what the model can do. It is what you can do with it.

What actually moved the needle for me

It was not a smarter chatbot. It was learning the plumbing. Over the last three years I learned Asana, then Zapier, then make.com and n8n, and honestly some of that already feels dated. The real leverage came from building databases, using my Vortex legal database of more than 140,000 Thai laws and Supreme Court decisions, using RAG so the AI answers from real sources, and automating the repetitive tasks that used to eat my week.

I will say something unpopular. AI is not that intelligent. These are predictive algorithms, very good at guessing the next word. The magic is not thinking. It is analysis. Give it a mountain of data and it finds the pattern in seconds, in a way no human can match. That part is genuinely impressive, and it is where the value lives.

For at least the last six months, Claude Cowork has been my number one tool, the engine under the database, the drafting, and the automation. That is also why I decided what I decided for June. I am opening this up. If you run a business or a practice and you want to use AI properly, as a tool with a human layer on top rather than a magic box, I am now offering AI business and legal architecture sessions. I will show you the workflow I use, where it saves you 80 percent of the time, and where the 20 percent of verification keeps you out of trouble. The rate is the same as a legal consultation, 2,000 THB per hour.

3. Retiring in Thailand: The Two Things That Trip People Up

With the tourist door narrowing, more of you are asking the obvious question. If I want to actually live here, what do I do? For anyone 50 or over, retirement status is usually the cleanest answer. The visa side is well understood. The two things that catch people out are money seasoning and what happens after you arrive.

The routes, in plain terms

The retirement visa is open to foreigners aged 50 and over. There are a few versions:

• Non-O (retirement): the workhorse. Can be set up and renewed inside Thailand every year. No mandatory insurance.
• Non-OA: applied for from your home country, valid one year, but it requires a police clearance and mandatory Thai health insurance.
• Non-OX: the 10-year version, which requires a higher bank balance of around 3 million THB.
• The LTR is the higher-net-worth alternative, with a longer term and a work permit included.

The part nobody plans for

Here is where I earn my fee. Two issues sit behind every retirement, and almost nobody handles them until it is too late.

First, tax. Thailand now taxes foreign income that you remit into the country. The good news is that there are legitimate ways to bring money in with little or no tax, if you plan before you transfer. A gift to a Thai spouse is exempt up to 20 million THB per year, with only 5 percent on anything above that. Money can also come in structured as a loan, or in other forms that are not treated as assessable income. The catch is that it has to be real, properly documented, and the money cannot quietly loop back to benefit you. Done carelessly it becomes a problem. Done correctly it is fully legal and it works.

This is not theory. In the last two months I ran several consultations exactly like this and saved clients millions of baht. I have also watched people wire 10 million THB into Thailand without a second thought and create a tax bill they never needed to pay. Think before you transfer, not after.

Second, your estate. If you live here for fifteen years and pass away without a Thai will, your Thai assets, your bank account, your car, your condo, do not simply go to your family. They can be frozen, and your heirs can be left fighting over them. I have seen worse. I watched a girlfriend empty a man’s bank account before his children back home had even learned that their father had died in Thailand. By the time they found out, the money was gone. The Thai court process to untangle an estate takes several months, sometimes far longer, and a good deal of money. A Thai will costs 3,900 THB. A living will, which sets out your medical wishes, costs 1,900 THB. It is the cheapest insurance you will ever buy, and the one people put off the longest.