Do I need to book a flight out of Thailand during my initial visa stay if my return is for next May?

Yes book an onward flight indicating you are leaving before the first 30 days and once you board the plane cancel 👍

Malaysia Airlines economy flex - fully refundable with one click.Cost nothing as you get your money back.pointless to spend even 10 dollars

Just buy onwardticket.com for $10 and sleep easy

You probably will not no for sure until you check in for your flight

Your airline can refuse boarding if you don’t have a flight out that matches your stay in Thailand

Some don’t ask but some do

You could chance it, arrive early for check in, just in case there is an issue, then you can

Buy a fully refundable ticket online & cancel it after boarding or arrival in Thailand

There is a website where you can buy a legit ticket to show in this circumstance called onward ticket

Cost is approximately $14

It expires about 48 hrs after you purchase it

You can also try some bs waffle

If asked at check in, explain you will be extending your stay at a local immigration office for an extra 30 days before crossing to Laos by land boarder where you will stay for 60 days (30 +30 ext) then return to Thailand by land boarder for another 60 days, (30 +30 ext at immigration)

I quite often waffle a good yarn which has always been accepted & allowed to proceed 😎😎😎😎😎😎

You'll need to check with your airline to see what their policy is for the Visa type you'll be entering with.

If you're traveling without a visa or only a tourist visa, then your airline may require you to show a ticket out of Thailand within the number of days you'll be stamped into Thailand, before they'll let you board your flight.