Taxes & Returns

@Rowan-Ash
Honestly, when you’re dealing with income from different states and juggling side gigs, taxes can get really tricky. It’s super easy to overlook deductions or get confused by the specific rules for each state. That’s when having a good accountant really pays off; they can help you avoid audits and spot credits that tax software might not catch. Just having that peace of mind is totally worth it.

@Juno-Pierce For 2026, the FBAR is due on April 15, but you receive an automatic extension to October 15 without filing any forms. Foreign Tax Credits (Form 1116) usually follow your tax return deadline. Missing these can be a nightmare, so it's best to stay ahead of the curve.

Hey @Orion_Leif just a heads-up on those RSUs before you make the move: the IRS and your new country's tax office are both going to want a piece of them. Since taxes are based on where you physically worked while those shares were 'earning,' it can get messy quickly.

My best advice: Start tracking exactly which days you work in each country right now. Talk to HR about updating your withholding to avoid double billing. It’s also a good idea to consult a cross-border tax professional. It’ll save you a massive headache (and potentially a lot of money) during tax season.

If I’m paying an overseas contractor around $10,000 through PayPal for work, but I’m not registered as a formal business, can I report this as a tax expense, or will it cause compliance issues since I'm not an official company?

@Mason said in 1040-NR Delays with IRS:

I filed a 1040-NR using a temporary SSN and have been waiting for a long time. At this point, is calling the IRS repeatedly actually helping? Should I try contacting a Taxpayer Advocate or re-file electronically? Has anyone else in this exact situation found a real solution to this long delay?

Long delays with 1040-NR filings and temporary SSNs are a huge headache in the U.S. Calling the IRS usually doesn't help once things hit manual review, but reaching out to the Taxpayer Advocate Service can be a lifesaver if the wait is hurting you financially.

And hey, don’t re-file electronically unless they tell you to; it just complicates things. Just stay organized with your records and keep an eye on your transcripts for any updates.

Look @Jordan your CPA is going to need more than just a 1099 to get this right — they really need the "nitty-gritty" details of your transactions. This means tracking exactly when you bought on PayPal, what it was worth in USD the moment you sent it to Stake, and any fees you incurred along the way.

The good news? Moving your own crypto between wallets isn't a taxable event. However, the IRS definitely wants its cut of your staking rewards and any time you sell or spend your coins. The simplest way to manage this without stress is to export CSV files from your platforms and use crypto tax software. It will save you a ton of manual math and help keep the taxman happy.

You can check your refund status using the official IRS “Where’s My Refund?” tool online or through the IRS2Go mobile app. Enter details like your Social Security number, filing status, and exact refund amount. The IRS typically issues refunds within 21 days of filing an e-return.

HSAs give you a triple tax benefit; they let you save for medical costs with pre-tax money. Your medical bill contributions and withdrawals are tax-free, lowering your taxable income.

Small businesses are mandated to withhold federal income, Social Security, and Medicare taxes from employee pay. Use IRS Publication 15 for guidance.

File Form 941 every 3 months and Form 940 once a year. Failure to comply can lead to fines and interest charges, such as those incurred for late Form 941 filings.

The type of federal tax form you need to file will depend on your business structure.

For Sole Proprietorship, File Schedule C (Form 1040). For partnerships and companies, they must use particular forms, such as the Schedule K-1 and corporate tax return (Form 1120).

In your case, I believe you are the owner, so proceed to file Schedule C (Form 1040).

When hiring W-2 workers, you must manage their payroll taxes, including Social Security, income, and Medicare contributions, and provide additional benefits such as unemployment insurance and health insurance.

However, 1099 contractors bear the responsibility for their own taxes and receive fewer benefits. W-2 workers have more control over their work, despite contractors offering more flexibility and fewer administrative tasks.

If your company wants greater control, then choose W-2; if your company needs more flexibility, then 1099 may be better.