Understood! Thank you for your insights. At the end of the day, I think providing information through my Italian company when applying for DTV is a solid option, just like you suggested. If it's true that they won't ask questions about it in the future, then that's even better.

@Todd ********

My bad, I didn't mean that literally, but according to the regulations, it's not possible to be considered resident in Thailand and Italy at the same time for the same income. Also, Italian tax rules could still consider me a tax resident if I maintain significant ties, such as having a VAT number and producing income through that company. Not exactly prohibited, but just a bad international approach.

@Greg *******

Hi, thanks for the feedback, it's smart! One of the reasons I'm interested in Thailand is its territorial tax regime, which works well for a US-TH structure, but not ideal for IT-TH. Eventually, would it make sense to just explain the thing in the cover letter? It's not like there's anything wrong with it in the end, it's all legal.