Staying in Taiwan on a multiple entry visitor visa - Visa runs as a visitor

I’ve got the following situation and could really use some advice or insights: I currently hold a passport that requires a visa for entry into Taiwan. My plan is to apply for a multiple entry visa in Taiwan and stay there for around a year, maybe a year and a half. The ultimate goal is to marry my partner, who is pursuing a Ph.D. in Taiwan, and then transition to a spouse visa.

I’m curious about the idea of doing visa runs during this period. How sketchy does this look to immigration? Are there risks involved in terms of being denied entry after a few visa runs and accumulating Taiwanese stamps on my passport?

Secondly, I work remotely for a company based overseas. Could this be considered illegal work in Taiwan? And what about taxes? Do I need to pay taxes in Taiwan for the income I’m earning while working remotely?

I’m hoping to gather some information to make more informed decisions. Thanks in advance for your help!

To answer that part: Yes, working without a work permit is illegal in Taiwan - even when the employer is outside of Taiwan. Also, you’ll be liable for taxes on income received from outside of Taiwan when the services were performed from within Taiwan.

Although some people will argue that the chances of getting caught are low, sometimes all it takes might be an angry or jealous neighbor who reports you to immigration. YMMV.

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you will find almost all the information you need in the following site.
https://www.boca.gov.tw/np-147-2.html

read carefully especially notes at the bottom of each page. visitor visa should be applied at a TECO outof Taiwan, and its validity may be from thtee months upto one year, so you may need to reapply for visa in one and a half years, depending on your visa’s varidity.

you said you need a visa, so you might be from special countries they apply different requirments. you could check here.

Procedures for Nationals of the Designated Countries Applying for Visitor Visas to the Republic of China(R.O.C.)

https://www.boca.gov.tw/np-150-2.html

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Have you looked into the Gold Card and see if you qualify?

Yes, I did look into it but I don’t fit the criteria, I don’t have enough years of experience in my area nor have a salary of 160k NTD

In my country’s TECO website it is mentioned that they provide multiple entry visitor visa for tourism/visiting family which would fit my situation the best.

This type of visa would have validity of 5 years, meaning I could theoretically enter Taiwan as many times as I’d like until 2028 but I’m worried of the immigration being suspicious of my back to back travels to/from Taiwan every 90 days

Family is not a boyfriend. A spouse yes. Taiwan does not recognize relationship if not married.

My mistake, the visitor visa for the purpose of visiting is described as “Visiting Family/Friends/Tourism/Cruise” by the TECO so yes it would fit my situation nonetheless

OK some advice, even if the visa is available you may not be granted a long stay. As you are aware they would ask how you intend to support yourself with current savings. Saying you are going to work in Taiwan ( even remotely ) would see you being rejected as you cannot do any work on a visitor visa. So don’t mention work at all.

there are people who do this for years without a visa, so as far as you can give them some impression that you have enough money to support your stay in Taiwan, maybe it is ok.