16 Do you know if H&R Block offers the same feature? That's what I've been using for years and would prefer to stick with it if possible.

21 Yes, H&R Block does offer 1099 filing capabilities in their small business versions. You'd need their Premium & Business or Business & Investment packages to access those features. However, if you're only filing one 1099, it might be more cost-effective to use one of the standalone services others have mentioned, since the upgrade cost for H&R Block might be higher than just paying for a single 1099 form processing. The benefit of using your existing tax software is everything stays in one system, which makes record-keeping easier for future years.

1 Thanks for this reminder! I completely forgot about that aspect. Would this go under "Contract labor" on the Schedule C, or should I list it somewhere else? I've never had this expense before.

Thank you so much! This is exactly what I needed to know. I'll go back and look for that option. Do you remember if it asks for any specific information about the foreign contractor?

It will ask for their name and I believe their country, but not much else. You won't need their tax ID number or anything like that. Just make sure you have good records of the payments in case of an audit - invoice, proof of payment, contract, etc. The key is documenting that the work was legitimate and for your business.

Actually, it depends on the tax treaty status with the specific country. Some countries require withholding regardless of where the work is performed. India (where OP's contractor is located) has specific provisions in its tax treaty with the US.

Can you really claim those deductions without receipts though? I worked construction under the table last year and literally have zero documentation for any of my expenses.

You can estimate reasonable expenses even without perfect documentation, but you should have some supporting evidence if possible. For example, with mileage, start a log now documenting your typical work travel patterns, then use that to reasonably estimate your past travel. For tools, take photos of what you own and research purchase prices online. The IRS does allow for reasonable reconstruction of records that were lost or never kept. Just be honest and realistic - don't claim $10,000 in tool expenses for a $26,000 job. And definitely start keeping better records going forward! Even a simple notes app on your phone where you take pictures of receipts is better than nothing.

I used TurboTax to amend a return with unreported income last year. It was pretty straightforward for the basics but I found it didn't give great guidance on what documentation I should keep or how to explain the situation in the amendment. For only $9k it might be fine, but if you can afford a CPA consultation, even just a one-hour session, they might catch deductions you'd miss and give you better peace of mind.

Actually that's not entirely accurate. You can be claimed as a dependent until you're 19, or up to 24 if you're a full-time student, as long as you don't provide more than half of your own support. So depending on the OP's situation, they could potentially be claimed for several more years.

I think you might be right! Looking at my W-2s again, my total wages for the year were around $145,000. I didn't realize that the excess refund was based on exceeding the wage base, not just on the total amount withheld. I thought if the combined withholding exceeded the max, I'd get the difference back regardless of my total wages. So even though I had more than $9,932 withheld between both jobs, I'm not actually entitled to a refund because my total wages didn't exceed $160,200? That explains the IRS letter then.

Exactly! You've got it now. The excess Social Security tax refund only applies when your total Social Security wages exceed the annual wage base ($160,200 for 2023). The system is designed to ensure you don't pay more than 6.2% on income above that threshold. Since your total wages were around $145,000, which is under the wage base limit, the full 6.2% Social Security tax applies to all your earnings. Even though the combined withholding might seem high, it's technically correct based on your total wages. When you respond to the IRS, simply acknowledge that you misunderstood how the excess Social Security tax rule works, and they should close the case without any penalties since it was an honest mistake.

That's the catch with having multiple employers in the same year! Each employer has no way of knowing how much you've earned at other jobs, so they each withhold the standard 6.2% on your earnings up to the $160,200 limit as if they're your only employer. The system is designed this way because employers don't share payroll information with each other. If you work for two employers and earn $100,000 from each in the same year, both will withhold $6,200 in Social Security tax, for a total of $12,400. Since that exceeds the maximum you should pay ($9,932.40), you can claim the difference ($2,467.60) as a refund on your tax return. But this only applies if your TOTAL wages exceed the $160,200 threshold.