Will I have problems entering Thailand on a Non-B visa given my immigration history?

No need to worry, I had my 15 months Ed- Visa expired on 8th Dec 2025. Went to Laos to change to Non-B, waited for 7 days, got E visa, took flight to Bkk, got grilled at immigration, officer speak in Thai and asked me to translate in English. Couldn’t do that, stepped aside, forwarded to Senior Officer, told I can speak Nit-noi 😄 however, I had my masters in Chinese language so that gave me an extra confidence, stamped and entered safely. Total process at immigration was 15 mins.

Good luck with you Non-B visa.

If your Non-B is approved, then you have a new visa... Won't have any problems.....

If you don't get the Non-B then who knows

You shouldn't have any problems getting the non-B nor entering with it, but you MUST cancel your education extension before you leave. If you don't do that, there are multiple reports of people not being allowed to exit through land border because they didn't cancel their extension, reports of people not being allowed to apply for a new non-immigration visa because they didn't cancel their extension, and people not being able to apply for a new work extension in Thailand because they didn't cancel their education extension and then having to pay a fine of 500 baht per day for failing to do so.