Thanks for this detailed list! We actually have most of these documents already because of the custody situation. The court order is definitely the strongest piece, but I hadn't thought about keeping a calendar of the actual days. That's really smart, especially for the first half of the year when he was with us most nights but not all. Do you know if there's a specific form I need to fill out to claim him since he's not my biological child? Or do I just list him as a dependent when filing?

You'll list him as a dependent on your tax return just like you would any other dependent. There's no special form required specifically because he's not your biological child. The regular dependency forms (Form 1040 and the associated schedules) are all you need. When you're entering his information in your tax software or forms, you'll need to specify your relationship to him. Since he's not related to you by blood or marriage, you would typically select "Other" and might need to write in something like "girlfriend's child" or "member of household" depending on the tax software you're using.

You also might qualify for the Earned Income Credit if your income is within the eligible range. Having two qualifying children (your daughter and potentially your girlfriend's son) could significantly increase that credit compared to just claiming one child.

I think I've already missed that window since it's been about 11 months since her passing, and as you mentioned, I've already completed the rollover into my 401K. I feel like I should have researched this better before making the initial decision, but I was dealing with a lot emotionally and just followed what the HR person at her company suggested.

That's understandable - these decisions often need to be made during difficult emotional times. Since the disclaimer option is no longer available, your best approach now is probably a combination strategy: First, designate her brother as the beneficiary for that portion of your 401K, ensuring he'll receive it if something happens to you. Then, work out a yearly gifting strategy once you're eligible for qualified distributions without penalties. You might also consult with an attorney about creating a simple agreement documenting your intentions, which could help clarify things for your own estate planning. Don't be too hard on yourself - you're trying to do the right thing in a system that doesn't make it easy.

This is actually not great advice. 401K loans become immediately due if you leave your job, and since OP is living overseas, that could be risky. Plus, if you can't repay the loan, it becomes a distribution with all the taxes and penalties. The gift tax concerns would still apply too.

That's a good point about the tax treaty - I didn't even think about that angle. Do you know if these tax treaties typically address dependents specifically, or are they more focused on the student's own tax obligations? Also, I've never heard of Form 8843 before. Is that something she would file separately from her regular tax return?

Tax treaties typically focus more on the student's own tax obligations rather than their status as someone else's dependent. The US-Canada tax treaty (Article XX) has provisions that may exempt certain scholarship or fellowship income from US taxation for Canadian students, but it doesn't directly address dependent status. Form 8843 is filed separately if she doesn't need to file a tax return, or alongside her tax return if she does need to file one. All F-1 students must file this form regardless of whether they earned any income, as it's essentially telling the IRS "don't count my days in the US for the substantial presence test because I'm exempt as a student.

Is the Other Dependent credit different from claiming someone as a dependent? I thought they were the same thing.

Thanks for explaining! Do you know if there's a way to check if they've received any information returns for me? Like the 1099-INT forms from my bank etc?

Yes, you can request your Wage and Income Transcript from the IRS, which shows all information returns filed under your SSN or ITIN, including 1099-INT forms from banks. You can request this online through the IRS website if you have an account set up, or by mail using Form 4506-T. Keep in mind that information returns for 2023 might not all be processed yet, as companies have until late January to file them. But you should definitely be able to see 2022 forms by now if they were submitted.

This isn't exactly right. Non-resident aliens have different filing requirements than US citizens/residents. Even if all US tax was properly withheld, you might still have a filing requirement to report the income. The rules around effectively connected income vs FDAP income are complex.

Thanks, this is exactly what I needed to know! For tracking business vs personal use, would a simple log be sufficient or do I need something more formal? I probably use it about 85% for the Amazon business and 15% for personal browsing.

A simple log would work fine, but be consistent with it. I recommend creating a spreadsheet where you track hours of use and categorize them as business or personal. Do this for a representative time period (at least a few weeks) to establish your usage pattern. The key is having something contemporaneous - meaning you're tracking it as you go, not trying to recreate it later if you get audited. Also take screenshots of your work on the computer for the business as additional evidence. The IRS is particularly interested in seeing that high-cost assets claimed as business expenses are actually being used for business purposes.

I think the "hobby loss rule" is that you need to show a profit in 3 out of 5 consecutive years to automatically be considered a business. Otherwise you need other evidence that it's a legitimate business attempt.