An FYI only. This is not a debate on insurance, etc., only my experience today 21/01/2020 at Ban Phu Nam Ron (Kanchanaburi) border crossing.
I attempted to border bounce today as I'll be flying back to the States in April and was attempting to circumvent a 90 day reporting at Chanwatana and currently I'm close to this crossing, touring.
I've been, since I arrived back at the end of December trying to get my insurance sorted and while close, they are getting the balance of my long term goals and short term sorted out. Things take time, I understand.
At the border (Thai side), there was confusion on my visa and I was pulled aside and taken to any area where we could talk with the supervisors (very polite, cordial). We discussed why I wanted to cross and that no my insurance was not yet processed, and that my visa was issued pre 01/11/19 when the new law went into place and, that I had traveled to Yangoon (Myanmar) via air in December without issue on my return. They agreed to speak with my Thai partner via phone and it was determined that due to my not having the certificate of insurance that I could NOT exit Thailand at this particular crossing and if I did, I might have to forfeit my O-A visa for a 30 day stamp.
This was done with the utmost respect to me and my situation and while of course I was disappointed, I understand that this is their border and their rules and was grateful that they took the time to try to work with me for a solution. I have nothing but praise for them in how I was treated.
O-A visa issued 28/10/2019
USA/Los Angeles
TLDR : Answer Summary
The author shares their experience at the Ban Phu Nam Ron border crossing while attempting to border bounce to avoid a 90-day reporting requirement. Despite the plan, they were informed that due to lacking the necessary insurance certificate, they could not exit Thailand without risking their O-A visa. The interaction with border officials was respectful, and the author expressed gratitude for their assistance.