This is super helpful, thank you! I didn't even know I could check what my employer reported to the IRS. Do these transcripts become available pretty quickly after employers submit them, or is there a delay? If my W2 just got generated recently, would it even show up there yet?

The wage and income transcripts are usually available by late May or June for the previous tax year, but there can be some lag time. If your employer truly just submitted your information recently, it might not show up yet. However, most employers submit their W2 information by the end of January, even if they're slow in getting the actual forms to employees. It's always worth checking - you might be surprised to find your information has been there all along, which could potentially strengthen your case about employer negligence for the penalty abatement request.

I don't think this advice is correct. Form 4852 is only if you NEVER received your W-2 or if it's incorrect. Since OP has the W-2 now, even though it's late, they should use the actual W-2 for filing, not the substitute form.

I completely forgot about social security taxes, thank you! Do you know if there's a minimum threshold for this? Like if I'm only there for 8 months, would that change anything about Social Security obligations?

For Social Security taxes, the duration of your stay doesn't typically create a minimum threshold. If you're employed by a US company, they'll generally continue to withhold Social Security and Medicare taxes from your paychecks regardless of where you're physically working, unless there's a totalization agreement with that country. As far as I know, the US and Kenya don't have a totalization agreement, so you'd continue paying into the US Social Security system. The good news is this means you'll continue earning credits toward your eventual US Social Security benefits, even while working abroad.

I'm not a tax expert, but from what I understand, Kenya typically doesn't consider you a tax resident unless you're there for 183+ days in a year. Since you were only there for 3 months (presumably less than 90 days), you likely weren't subject to Kenyan income tax. If you did everything correctly with your US taxes and reported all your income there, you probably don't need to worry about filing anything retroactively for Kenya. But if you're concerned, it might be worth consulting with a tax professional who knows the Kenyan tax system.

That's a relief! Yes I was there for exactly 89 days and did report everything on my US taxes. Was worried I might have some surprise tax bill waiting for me from the Kenyan government. Thanks for the info!

TurboTax Self-Employed does have an estimated tax calculator, but in my experience it doesn't handle the annualized method very well. It more focuses on the equal payment method. I ended up using the IRS worksheets anyway. QuickBooks Self-Employed does a better job with variable income and quarterly calculations, but it's still not perfect for true annualization calculations.

Thankfully I don't have any capital gains stuff to worry about right now! It's just straight freelance income. If that changes I'll definitely get professional help.

Ok this is at least some good news! Do you know roughly how much the stimulus payments were? And do I need any special documentation to claim them now?

The stimulus payments totaled $3,200 per eligible adult - $1,200 for the first payment, $600 for the second payment, and $1,400 for the third payment. There were additional amounts for dependents too. You don't need any special documentation beyond what you'd normally include with your tax return. When you file, you'll just need to complete the Recovery Rebate Credit section where you'll indicate that you didn't receive the payments previously. Most tax software will walk you through this with a series of questions about which payments you received.

This is good advice, but I don't think there's any penalty for filing a $0 balance or refund due return after the statute of limitations has expired. The IRS won't process the refund, but it helps complete your record.

8 I used FreeTaxUSA last year when I had a similar 1099-K issue. They do give you more control, but they still directed me to Form 8949 rather than Schedule 1 line 24z. The interface was pretty straightforward for entering each item, though.

14 Thanks for sharing your experience! I'm starting to accept that Form 8949 is just the way I'll have to go, regardless of which software I use. At least FreeTaxUSA is more affordable than some of the other options I was looking at.

11 The threshold is supposed to be $5,000 for tax year 2024 (filing in 2025). The IRS announced this change after delaying the $600 threshold implementation multiple times. That should give occasional sellers some breathing room.