What is the best way to extend my stay in Thailand as a Canadian expat with a non O (volunteer) visa and work permit?

Question

Hello. I currently have a non o (volunteer) Visa and work permit. The Visa expires end of May and the work permit mid July. In June I am planning to return home to Canada for a short visit. When my Visa expires at the end of May, I will be leaving my volunteer position and giving up my work permit (cancelling it correctly). I am hoping to stay in Thailand until mid June. Is the best way to do this a quick land border run near the end of May and arrive back with a Visa exempt stamp for 30 days (Canadian)? After leaving Thailand, in Canada I plan on applying for a single entry 60 day tourist Visa to return with in July.

My question is, is there any risk doing a land border crossing or coming back with a tourist Visa after being in Thailand for a long time on a non o and work permit? I have been on 2 non o visas with work permit since 2015, with only one Visa exempt stamp from 2015 and no previous tourist visas. 

Thank you for your advice!

My question is, is there any risk doing a land border crossing or coming back with a tourist Visa after being in Thailand for a long time on a non o and work permit? I have been on 2 non o visas with work permit since 2015, with only one Visa exempt stamp from 2015 and no previous tourist visas.

Thank you for your advice!

Talia ****** · Accepted Answer

The user is asking about the best approach to extend their stay in Thailand as their non O (volunteer) visa is expiring soon. They are considering a border run to obtain a visa exemption stamp for 30 days upon re-entry and plan to apply for a single-entry 60-day tourist visa from Canada later. They seek advice on the risks associated with this strategy, given their history with non O visas and work permits since 2015.