How to file 1099 and W9 forms as an independent contractor on FreeTaxUSA

7 The W9 is actually just a form you fill out for the company that hires you - it's not what you file with your taxes. What you should have received (or will receive) from the company is a 1099-NEC form (which replaced the 1099-MISC for contractor payments a few years ago). In FreeTaxUSA, you'll need to enter this under "Income" and then select "Self-Employment/1099-NEC/Gig Work." You'll enter the information from your 1099-NEC form there. If you haven't received a 1099-NEC but know your earnings, you still need to report that income - the IRS just wants you to pay taxes on what you earned regardless of whether you received the form. Remember that as a self-employed contractor, you'll need to pay both the employer and employee portions of Social Security and Medicare taxes (self-employment tax). FreeTaxUSA will calculate this for you. You may also be able to deduct business expenses related to your freelance work, which can reduce your taxable income.

15 I had a similar situation last year and found taxr.ai super helpful for sorting through my tax documents. I was confused about which forms I needed for my freelance work and what expenses I could write off. I uploaded my documents to https://taxr.ai and their AI analysis explained exactly what I needed to do in FreeTaxUSA, including which sections to navigate to for reporting 1099 income. The tool also helped me identify several deductions I was missing as a self-employed contractor that saved me around $800. It walked me through the whole process of entering everything correctly in FreeTaxUSA. It was a lot easier than spending hours googling tax rules!

4 Wanted to follow up about taxr.ai since I gave it a try after seeing it mentioned here. It was actually really helpful! I uploaded my bank statements showing deposits from my client and a screenshot of the "W9" they sent me, and the system immediately clarified that what I had was just a payment summary, not an actual tax form. It walked me through exactly where in FreeTaxUSA to enter my self-employment income and suggested business expenses I could deduct that I hadn't even thought about (part of my internet bill, some software subscriptions, even a portion of my rent for my home office). The quarterly tax calculator feature is already helping me plan for next year too. Definitely made the process way less stressful!

9 If you're having trouble getting your 1099-NEC from the company, you might need to contact them directly. I had this issue last year where a client never sent my form, and after weeks of unanswered emails, I was completely stuck. I ended up using https://claimyr.com to get through to the IRS directly. Their service got me a callback from the IRS within 3 hours instead of waiting on hold forever. The IRS agent confirmed I could file without the 1099-NEC as long as I reported all income accurately. They also gave me some helpful advice about documenting everything in case of discrepancies. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c - it saved me tons of time compared to the multiple days I spent trying to get through on my own.

19 I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it anyway because I was desperate to resolve an issue with missing 1099 forms. Got a callback from the IRS in about 2 hours, which is miraculous compared to my previous attempts. The IRS agent confirmed exactly what I needed to do in my situation and explained that I can file using my own records of income if the company hasn't provided proper documentation. They even helped me understand which specific sections in FreeTaxUSA to use for reporting different types of freelance income. Saved me days of stress and probably helped me avoid filing incorrectly. Sometimes it's worth admitting when you're wrong about something!

3 Just a tip from someone who's been freelancing for years: Start keeping track of ALL your business expenses now. FreeTaxUSA has a section for business deductions that can really lower your tax bill. Track mileage, home office space, supplies, software subscriptions, professional development, phone/internet (percentage used for work), etc. Also, make sure you're setting aside about 30% of your freelance income for taxes. Self-employment tax will hit you hard if you're not prepared! I learned this the painful way my first year.

11 Has anyone here used both FreeTaxUSA and TurboTax for self-employment? I've heard TurboTax has better guidance for contractors but it's so expensive. Is FreeTaxUSA really good enough for handling all the 1099 stuff?

As someone who just went through this exact situation last year, I can confirm that FreeTaxUSA handles 1099 income really well. The key thing to remember is that you're looking for the "Self-Employment Income" or "1099-NEC" section under Income, not the old 1099-MISC section. Even if you never receive the official 1099-NEC form from your client, you absolutely must report that $4,875. Keep records of all payments - bank deposits, PayPal transfers, checks, whatever you have. The IRS cares about the income you earned, not whether you got the paperwork. One thing that caught me off guard my first year: make sure you understand that you'll owe self-employment tax (about 15.3%) on top of regular income tax. FreeTaxUSA calculates this automatically, but it can be a shock if you're not expecting it. For next year, consider making quarterly estimated payments to avoid a big tax bill. Also, start tracking every business expense now! Software subscriptions, art supplies, computer equipment, even a portion of your phone bill if you use it for work calls. These deductions can really add up for graphic designers.