BritTim

As others have pointed out, there are no rules on this. It depends on where you enter Thailand, the individual immigration official you encounter, and the overall impression you make on the official. You can often help yourself in marginal cases by arriving well groomed, and conducting yourself confidently but politely. Your immigration history is not extreme at this time. I would not be surprised if you encountered some questioning if you enter visa exempt, but a denied entry is highly unlikely. Going forward, though, if you want to be a long stay tourist, use actual visas, and try to use land crossings or the safest airports (such as Chiang Mai).

In practice, you are extremely unlikely to have a problem on arrival in Bangkok if you have no onward flight reservation. However, many airlines will refuse to allow you to check in without one. You can buy a cheap throwaway ticket from Bangkok to any destination, or look at flight ticket rental websites that allow you to have a valid booking for a short while to (historically) circumvent required flight reservations by airlines, embassies etc.

Indeed! In the worst case, at Suvarnabhumi, it can take as long as 20 minutes (though I have never actually been that unlucky).

Of course, we laugh at that, but in 2023 a trans man may be able to become pregnant.

Correct. There is no such Thai regulation. There is a Cambodian law that, in most cases, requires people entering Cambodia to stay at least one night, but this is nothing to do with the Thai authorities.

It depends on where you enter Thailand, although (in some cases) it can vary depending on which immigration official you encounter. Historically, with actual tourist visas, I told people they were safe at most land crossings, and also when flying in to Chiang Mai or U-Tapao. When using visa exempt entries, they were safe using their two per calendar year by land almost everywhere, but to avoid Poipet like the plague. Visa exempt entries should not be used at airports at all once your immigration history becomes questionable, though I never heard of a denied entry at U-Tapao. The 180 day guideline is used by many immigration officials who believe long stay tourism should not be allowed (in spite of the fact that many senior officials in various branches of government believe long stayers like snowbirds should be encouraged). It is, by the way, perfectly valid for officials at airports to scrutinise requests for visa exemptions. The official is playing the same function as a consular official when you are applying for a visa. This is not the same thing as deciding whether you meet the requirements under Section 12 of the Immigration Act for a denied entry. What is not legal (but as others will point out, nothing you can do anything about) is an official who is opposed to long stay tourism on principle telling you straight that he is denying you entry with a valid visa because you spend too much time here, stamping your passport with a bogus reason for the denial (often, that you are not able to financially support yourself during your stay). Effectively, the official is refusing to honour the visa issued by a Thai embassy. There are two motivations. The first is not logical. Some officials are simply opposed to long stay tourism on principle, and tend to hate foreigners generally. That disease is present in a particularly virulent form in the senior officials at Aranyaprathet. The second is that the officials make a pretty penny facilitating entry for people who are absolutely desperate to enter. If you quietly talk to the fixers on the Cambodian side, they will tell you the cost. This is not just a few hundred baht like with the scam run at Phu Nam Ron (when it was open). Visa run companies would be willing to pay that at Poipet. No, at Poipet, they demand over 10,000 baht for the no hassle experience.

Ideally, do the 90-day address notification, though nothing terrible will befall you if you omit it, given that you plan to leave Thailand anyway shortly thereafter. Your last date to leave Thailand (assuming you do not extend) is March 1st.

You will need the police report that reported your old passport lost. The officials will then find your record in the computer, and put stamps in your new passport indicating the immigration history, and stamp you out (fining you for the overstay assuming, as now seems very likely, this applies). Allow some extra time, but do not worry. Apart from a few questions, there is no real problem as far as Immigration is concerned. Do not get arrested for something else while in Thailand without your passport and on overstay! This can lead to major drama, whatever your excuses.

You have it right. If it proves possible, your plan is absolutely fine. I note that VietJet now has direct flights from HCMC to Chiang Mai which makes it a much more attractive option than formerly for those who want to enter there. One issue: you need an appointment to apply for a visa at the Thai consulate in HCMC, and this is usually only possible if booked well in advance.

Whether all this is truly necessary is a matter of debate. However, the suggestion to fly back into Chiang Mai (based on historical experience) is fairly safe. Even safer is to enter Thailand with an actual tourist visa rather than visa exempt (assuming you do not yet have the documentation to apply for the new Non Ed visa). Phnom Penh is not a great place to apply for tourist visas. I would consider flying to Hanoi. There are fairly cheap flights available from Hanoi to Chiang Mai, and the Thai embassy in Hanoi is good for a tourist visa application.

You will need to cancel your current extension based on studying before you can virtually simultaneously apply for the extension based on marriage. If the school provides you with a letter to the effect that you have left the course of study for which you were provided the extension, this will be easy. Otherwise, the immigration office may not cooperate. Before going ahead, be sure that your marriage extension will go smoothly. I would suggest taking your proposed documentation supporting the marriage extension application to your local immigration office, to ask if anything else will be needed, before cancelling the existing permission to stay. If all else fails, you can leave Thailand to somewhere like Savannakhet (without a re-entry permit) and apply for a Non O visa to visit your Thai wife, subsequently extending in Thailand.

If your first flight is an early morning flight, it will usually be on time or close to it. Air Asia flights later in the day are often late, sometimes by multiple hours. If missing the second flight would be only a minor inconvenience, I might risk it if arriving on the first flight in the morning. Otherwise, allow three hours.

Think very, very carefully before you report the passport to the UK embassy as lost. It may eventually become necessary but, once you do so, there will not any longer be any chance of a simple resolution of the problem. That will be true even if, not improbable, the passport materialises with your extension a day or two after you tell the embassy your passport is gone. Your passport will have been cancelled in the UK's system, and no longer be valid for travel.

There are quite a number of jobs that are possible with extended breaks. Some examples are (i) English teaching, where you can be engaged on and off to teach specific groups or individual students (schools love that: no work permit complications, and engaging and dropping teachers as demand fluctuates); and (ii) dive masters, where there are often distinct seasons where your services are needed. Apart from that, some may work on an informal basis, doing almost anything for which they have the skills. That does not mean that I support immigration officials who simply assume (without evidence) that someone cannot just be in Thailand for pleasure because they have been here so long.

By air, there is no fixed limit to the number of border runs and visa exemptions that are permitted. By land, you are entitled to two visa exempt entries per calendar year. Thus, any you received last year are now irrelevant. You can still get two in 2023. With a visa, you can , in principle, enter Thailand as many times as you like whether by air, land or sea. However, some immigration officials at some entry points do not like long stay tourists, and might create problems if you have spent long periods in Thailand as a tourist.

You say "the boss has disappeared"?!??! I am at a loss on what to advise you. It appears that the person who would know the status and whereabouts of your passport is no longer to be found. How long has "the boss" been missing? This is such a weird situation that half the posters here are going to assume this is a made up story. Think carefully and decide whether you can share the name of the agent. If your story is based in fact, people here who have used the same agent might be able to diagnose the probable status.

Check if your embassy in KL will process an affidavit of freedom to marry without your presence and, if so, try to find a lawyer in KL to handle everything for you.

What a mess! I assume you are not a Singapore citizen. Based on that, forget applying for the O-A and O-X visas which are only available from your home country. If you are married to a Thai, you could apply for a Non O (spouse) visa. Most likely, Singapore does not offer a regular Non O visa for those over age 50 (what is often called "retirement visa") but you could ask them. If already in Thailand on an extension of your permission to stay based on retirement, and meet the requirements, you can apply for a further one-year extension at your local immigration office. You can apply right up to the expiry of your current permission to stay.

Whenever you are flying on an IATA member airline (pretty much all the major ones) and are unsure whether you meet the requirements for your trip, the IATA Travel Center site is up to date and reliable. For a planned trip to Thailand, you can start at https://www.iatatravelcentre.com/TH-Thailand-passport-visa-health-travel-document-requirements.htm, enter all the information requested, and it will tell you of any requirements you do not satisfy. Screen shots from this site can be useful if you have any problem at airline check in.

It is called a "border pass" which accurately reflects its permission to cross and stay in the vicinity of the border crossing. Apart from limits on how far you can stray, you must also return through the same crossing. I believe you are also limited to a three-day stay in Laos.

There is no official limit (and never has been). However, some immigration officials dislike the whole idea of long stay tourism, which they believe should not exist. They can try to suggest that you cannot really be a tourist if you stay very long periods, and ought to have some other visa rather than your status as a tourist. There are no legal mechanisms for them to enforce their prejudices. In most cases, you may be hassled at some airports, but will not be denied entry if you use actual tourist visas. With visa exempt entries, the officials has discretion, and it is appropriate for them to use that discretion, to prevent you using visa exemptions to live indefinitely in Thailand. When you have actual visas, determining whether you are a legitimate long stay tourist should be the responsibility of the embassy/consulate. The immigration official has no business deciding he will not honour the visa. That said, those a very long time in Thailand as a tourist (with only short gaps) have been known to be denied entry on bogus grounds. Especially if entering with actual tourist visas, you definitely do not need to worry until you have been over six months in Thailand over the previous year. At some airports (notably Chiang Mai) there have never been reports of inappropriate denial of entry to those with visas, regardless of your prior history of stays as a tourist. Just be aware that both Bangkok airports, and some others, could be problematic under some circumstances.

There is no law against what you propose. There is a very small chance that the wrong immigration official at Samui could (improperly) try to suggest you are "gaming" the system with your in/out, and hassle you about money and onward flight ticket.

According to https://www.bankbazaar.com/visa/thailand-visa-on-arrival.html, there is no Visa On Arrival desk for Thailand at the Chong Mek crossing. That is only a single source, and may be out of date, but is more likely to be correct than wrong. The UK Thai Embassy site (https://london.thaiembassy.org/en/publicservice/115123-visa-on-arrival?page=5d6636cd15e39c3bd00072dd&menu=5d6636cd15e39c3bd00072de) has a similar, but smaller, list that also does not have Chong Mek, but Thai embassy/consulate sites are notoriously unreliable sources of information. The best solution may be to get a re-entry permit during the quick initial trip to Thailand. This will protect the 30-day permission to stay from the initial VOA. The re-entry permit costs 1,000 baht, and is available from the immigration office servicing the province where you are staying in Thailand. If you have no opportunity to acquire a re-entry permit in advance, but plan to exit at Chong Mek on a regular week day, there is probably an immigration office in Ubon Ratchanthai province that will issue re-entry permits for people exiting at Chong Mek. If you cannot get a re-entry permit due to timing, there is no obvious good solution. There is an E-VOA service, allowing you to apply for the VOA in advance, but the delivered electronic visa can only currently be used at four main airports.

Since you want to use Savannakhet, while minimising time off work, here is my suggestion on travel. Take an overnight VIP bus from Bangkok to Mukdahan. This connects perfectly with the first international bus from Mukdahan into Savannakhet in the morning with no rush to get in your visa application before the 11:00 am cut off time. For the return, after collecting your passport the following day at 2:00 pm, plan on getting an Air Asia fly-ride ticket to return from Mukdahan to Bangkok, arriving in time for a needed night's sleep before work the next morning. There to no reliable way of flying that will get you to Savannakhet in time for the visa application the same day.

PR holders cannot get re-entry permits at the airport, as far as I know. Their re-entry permits are different, and must be acquired in advance from an immigration office.