Yes.

90 days not connected to visa. But you can do it while you're there to extend visa.

If I understand correctly from this page, you need work permit and "Fit to Fly" certificate. But it's really up to the airline whether they let you on the flight or not, so contact them and ask them what you need.

Good luck.

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It doesn't say anything about any kind of certificate required for WP holders entering the country, only for transit or Thai nationals. Something is missing here.

Should be able to get 30 days the first time without a letter. That's the normal rule.

Some offices now allowing a 2nd 30-day extension with no letter, but contact the office to check first.

You can IF you can come back a few weeks ahead of the expiry date and IF the school can get you a work permit in time to extend. If either of these things don't work out, you'll need to start over with a new B visa.

ATM foreigners aren't being allowed to enter Thailand (unless they have an impossible to get medical certificate), so once you leave you might not be able to get back in for an extended period of time.

As others have mentioned, you'll need to get a Re-Entry permit before you go.

@Am***

I've sent you a PM

Did you go to an agency?

If so, which agency?

Yep. Penang. Go to Banana House.

The next announcement will be about "express service" fee if you want to jump the cue ;)

This will likely cause delays for anyone doing a Penang visa run

Go on time for your extension or you could be denied.

The 18th is a Sunday, so you'll probably need to go on the 16th to get your extension.

See what date they give you on the extension, then decide if you want to overstay and pay the fine or do it legally and get another extension or do a border bounce.

Whether or not it will affect your holiday in December is hard to stay. They might be especially picky in terms of onward ticket, having 20k cash available, etc. if they see you've overstayed in the past. Might be safest just to pay your money for the bounce/ second extension and save the stress in the future.