1) should proof of onward travel be within 60 days or may it be within 90 if planning on 30 day extension?
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TLDR : Answer Summary
When flying into DMK on a tourist visa, it's necessary to present proof of onward travel. Typically, this should be within 60 days of your arrival. However, if you plan to apply for a 30-day extension of your tourist visa, you may argue that your proof can extend to within 90 days, depending on your travel itinerary and the discretion of the immigration officer.
90 DAY REPORTING RESOURCES / SERVICES
Use the trusted Thailand 90 Day Reporting Service to get your in-person report done and mailed to you for as low as 375 THB (even if the online system doesn't work for you).
For immediate assistance, contact Thai Visa Centre directly via LINE at @ThaiVisaCentre or Email them.