Backstory: My visa expires in a few days and I don't want to go home to Canada. Life is wonderful and normal here in Taiwan.

I can either go back home or overstay. Specifically, I'd like to overstay here for a month or 2, and will be travel out of here to other COVID-safe countries soon (e.g. Vietnam.) This likely won't be possible for much longer out of Canada.

Let me get to the point: I'm okay with getting a ban/fine from Taiwan. Let's say I get a ban for 2 years.

But after serving this ban and paying fees, will I continue to be scrutinised more every time I try to return to Taiwan? In my future, I absolutely want to keep returning to Taiwan on visa-free entry trips and potentially start a business. In other words, are there consequences beyond simply the ban/fine they give me immediately? I'm trying to see if this is worth overstaying.

Thanks for helping in advance.

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    I vote to close this question, we don't give advice to break the law. – Max Jun 15 '20 at 22:40
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    Have you attempted too ask the local authorities if you can remain longer? That is really the simplest method to resolve your problem. – Mark Johnson Jun 15 '20 at 22:50
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    If you show that you're willing to break the rules you can be sure that the Taiwanese authorities will not be wanting you back. If you do incur a ban you'll need to put this on any visa application you make elsewhere and that will make getting those visas much more difficult. In short, follow the rules, don't lie to immigration. – user105640 Jun 15 '20 at 23:04
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    You may want to see if you are eligible for the Taiwanese automatic visa extension. It looks they have been granting 30-day extensions every 30 days during the pandemic, though this will of course presumably end at some point. – mlc Jun 16 '20 at 5:48
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    I’m voting to close this question because its asking advice on breaking the law. – Anish Sheela Jun 16 '20 at 6:00

Taiwan currently has an amnesty program for foreign nationals who want to overstay their visas.

"Under the program, there will be no mandatory detention, while the maximum penalty will be NT$2,000 (US$66) and no re-entry ban, compared with detention, a maximum fine of NT$10,000 and an entry ban of 1 to 8 years for those who do not voluntarily contact immigration authorities"

Go talk to a Taiwanese immigration agency official.

Full details are here: https://focustaiwan.tw/society/202003200006