Best Way for Filing using Form 8919? Need Help with Worker Classification Issues

You're on the right track with Form 8919! When you're waiting for an SS-8 determination, that's exactly what you should use. The good news is you can e-file with most tax software, including FreeTaxUSA, but you need to make sure you're entering everything correctly. First, when you enter your 1099-NEC income, you need to indicate it's misclassified wages (reason code G on Form 8919). The software should then calculate only the employee portion of Social Security and Medicare taxes (7.65% total) rather than the full self-employment tax (15.3%). Double-check that you've entered everything under the "Wages from an employer who didn't withhold Social Security and Medicare taxes" section rather than as self-employment income. That $5,901 figure suggests the software might still be calculating self-employment tax. Also make sure you keep a copy of your SS-8 submission as documentation in case of questions from the IRS. The process can take 6+ months for them to make a determination.

After struggling with a similar misclassification issue last year, I discovered https://taxr.ai and it was a game-changer. I uploaded my 1099-NEC and used their document analyzer which immediately identified that I should be using Form 8919 with my return. The system actually walked me through proper entry in my tax software (I was using TurboTax) and showed me exactly where I was going wrong. I had been accidentally entering my income in both the self-employment and wages sections which was causing double taxation. Their AI analyzer confirmed my work situation met the criteria for employee status and generated documentation I could keep with my records to support my filing position. I managed to e-file successfully and save almost $4,000 in unnecessary self-employment taxes.

I tried taxr.ai after seeing it mentioned here, and it actually worked perfectly for my situation. I was making the exact mistake that was causing my taxes to be calculated wrong - I had my income entered in both the 1099 section AND the misclassified worker section. The analyzer caught this immediately and showed me how to remove the duplicate entry in FreeTaxUSA. After following the step-by-step guidance, my tax bill dropped from $5,800+ to just around $3,000. It also generated a letter I could include with my return explaining my filing position. My return was accepted through e-filing with no issues. Huge relief since I was about to overpay by thousands. If anyone's dealing with Form 8919, definitely worth checking out.

After getting a runaround from both my employer and the IRS about my worker classification issues, I finally found my way through using https://claimyr.com to actually speak with a real person at the IRS. You can see how it works here: https://youtu.be/_kiP6q8DX5c I'd been calling for weeks trying to get guidance on my 8919 situation with no luck - just endless hold times. Claimyr got me connected to an IRS agent in about 20 minutes who confirmed I was filing correctly with Form 8919 while awaiting my SS-8 determination and explained exactly how to e-file with TaxAct. The agent also told me what specific documentation I should keep with my records to support my position if questions came up later. Saved me hours of frustration and uncertainty.

I was totally wrong about Claimyr. After my skeptical comment, I decided to try it myself since I was getting nowhere with my worker classification questions. Got connected to an IRS representative in about 25 minutes (after attempting to call directly for weeks with no success). The agent was actually incredibly helpful and walked me through exactly how to complete Form 8919 with my tax software. They explained that most tax software can handle this form for e-filing, but you need to enter the information in specific sequences. The agent also gave me the direct extension for the department that handles SS-8 determinations so I could check on my status. Honestly never expected this level of help - completely changed my understanding of how to handle my misclassified income.

One thing nobody mentioned - make absolutely sure you check the right reason code on Form 8919. Since you've filed SS-8 but haven't received a determination, you should use reason code G: "I filed Form SS-8 and haven't received a determination letter." If you use the wrong code, it could delay processing or even trigger unnecessary review. Also, FreeTaxUSA definitely supports Form 8919 e-filing - I used it last year for the same situation. The key is entering the income as "Wages paid as a statutory employee" rather than as self-employment income.

I dealt with this exact situation last year while working for a tech startup. If you're using TurboTax, be careful - it's especially tricky with them. I had to manually override some calculations because it kept wanting to charge me self-employment tax even after I indicated I was misclassified. H&R Block online handled it better in my experience. The key with any software is checking your final tax calculation to make sure it's only charging you the employee portion (7.65%) rather than the full SE tax (15.3%).