I'm planning to leave Thailand for around 7 weeks, Dec - Feb.  Been informed that in order to get the Thailand pass to re-enter Thailand i will need to show $50,000 medical insurance valid till the date of my current extension of stay expiry (20th Sep). This is compulsory medical cover for retirees via the back door

This is being discussed in few threads. Along with conflicting reports. 

Some have reentered with insurance for various periods (eg 60 days) and have been stamped in according to their reentry permit. 

The very vague "insurance required for duration of stay" is in itself a nonsense.

 

Daily the forum is advising folk entering on visa exempt with 30 day covid insurance with the intention of obtaining a non O and then 12 month extension.

 

Some with valid non O-A (not extension) would be normally stamped in for 12 months.

 

IMO it's unclear at this stage. 

Hopefully a more definitive set of rules will be  announced.

 

R Burrow pointed this issue out week or two ago. Obviously the set period of insurance required for those returning with reentry permit should be set. 30 days good option.

 

Word to the wise, the situation is very fluid right now, between now and until you'll to plan coming back to Thailand the rules and regulation might change by than, keep your eyes and ears open and follow discussions in this forum for the latest...