So I did my 90-day probation report today and took only about 15 min. Hooray! Next I asked if I will need proof of health insurance when I extend my Non O-A in 2 months and the official at the front desk, who looked like he was very bored and couldn't smile if he tried, said yes.
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TLDR : Answer Summary
The user completed their 90-day probation report and inquired about the necessity of health insurance proof when extending their Non O-A visa. An immigration official confirmed that health insurance is required for the extension.
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James Miller, I posted as an update as a convenience to others that want to know whether the Chiang Mai immigration will be enforcing the health insurance requirement. My choice of how to deal with it isn't important.