Finishing JET ALT, need to file back taxes, a few questions

Hi all!

I've recently become aware that I owe some back taxes from dividends and sales of shares back in my brokerage in the U.S. I was a non-permanent tax resident who just hit 5 years in Japan (as of yesterday) and finished my stint on JET and am starting a new job soon. I need to pay back taxes for 2019-2023. I've got all my numbers together (dividends, capital gains, and USD/Yen exchange gains (best guesstimate on my ACB)) and intend to enter it all on the NTA tax prep site. I have a few questions if you don't mind.

  1. For dividends, I understand that dividend taxes are remittance based while an NPR. Just to simplify numbers, let's say I got 1,000 yen of dividends on Day 1, then 1,000 yen of dividends on day 10. I remitted 500 yen that year. So when I enter the dividends, I would put Day 1 = 250 yen, Day 10 = 250 yen. Correct?

  2. Capital gains. Let's say, I already had 900 shares in the years prior to coming to Japan. Once I come to Japan, I acquire another 100 shares (via dividends). Again, still an NPR in Japan, so some is subject to remittance based taxation. 10% of shares are in the NPR period, and 90% of the shares are from prior to coming to Japan. Let's say in 2023 I sell everything. In this case, I take the total of the sale and subtract the average cost basis total to get the profit. Then, I take 10% of the profit and that is taxable regardless because it was acquired after I arrived in Japan, and the remaining 90% is subject to remittance based taxation. Is this understanding correct?

  3. I would rather my new job not know about my tax issues. I think I can keep that info from them by having my residence taxes sent directly to me. Is this correct?

  4. Lastly, I arrived just before the 2019 U.S. treaty revision, and was tax exempt from my teaching income for the first two years (July 2019-July 2021). How do I submit my taxes and still retain that tax exemption for teaching while paying taxes on the rest?

Thank you all for any advice! This sub has been a life saver!

by japan20240729

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