From another thread, the same scenario:
“Entered Thailand at Suvarnabhumi yesterday afternoon with OA visa expiring on 19 Feb 2020. Stamped in until
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/2020 (i.e. 365 days from yesterday's date). No questions, no queries, no strange looks, no request for proof of insurance. Once stamped I stuck my neck out and asked the IO what the latest was on the insurance angle. He said it's a Visa application requirement, the same as police report and disease report, not an immigration issue. This is first hand, it's me (not hearsay), it was yesterday.”