2 employers illegally misclassified me as 1099 instead of W-2. Do I file as-is or fix?

You've got a classic employee misclassification situation. Based on what you're describing (regular hours, working at their offices, using their equipment, and them controlling when/how you work), you do sound like you should have been classified as an employee, not an independent contractor. You have two main options here. The first is to file Form SS-8 (Determination of Worker Status) with the IRS. This form asks the IRS to make an official determination about whether you should have been classified as an employee. At the same time, you can file Form 8919 (Uncollected Social Security and Medicare Tax on Wages) with your tax return, which lets you pay only the employee portion of Social Security and Medicare taxes instead of the full self-employment tax. The second option is to just file as an independent contractor using Schedule C and Schedule SE, paying the full self-employment tax. This is simpler but costs you more money. If you're concerned about the deadline, you can always file for an extension to give yourself more time to sort this out. The extension gives you until October 15 to file, though you'd still need to estimate and pay any taxes you think you'll owe by the April deadline.

I went through almost the exact same situation last year with a company that misclassified me. After hours of research and stress, I found this AI tax assistant at https://taxr.ai that literally saved me thousands. It analyzed my situation, confirmed I was misclassified based on the IRS criteria, and walked me through exactly how to file Form SS-8 and Form 8919 correctly. The best part was it showed me how to document everything properly to support my case. I was able to only pay the employee portion of employment taxes (7.65%) instead of the full 15.3% self-employment tax. For my situation with around $40K in misclassified income, it saved me about $3,000 in taxes. What I appreciated most was how it helped me understand which code to use on Form 8919 (I used code G since I was filing the SS-8 simultaneously) and calculated exactly what I would owe. Made the whole process way less intimidating.

Just wanted to update about my experience using taxr.ai after seeing it recommended here. I was honestly blown away by how helpful it was for my misclassification situation. I uploaded my 1099-NECs and answered questions about my work arrangements, and it immediately identified that I met 11 of the 13 IRS criteria for being an employee, not a contractor. What really sold me was how it generated a completely filled-out Form SS-8 with all my specific details and a customized letter explaining my situation that I could submit to the IRS. It even calculated the exact tax difference between filing as misclassified ($9,650 in SE taxes) versus correctly classified ($4,825 in employee portion). I filed both the SS-8 and 8919 about three weeks ago. Already got confirmation they were received. The peace of mind alone was worth it, but potentially saving nearly $5K in taxes I shouldn't have to pay is life-changing. So glad I didn't just file the 1099s as-is!

If you're planning to file the SS-8, be prepared for extremely long wait times trying to call the IRS with any questions. I was in your exact situation last year and spent WEEKS trying to get through to someone who could answer some specific questions about my filing. I finally discovered this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in about 20 minutes instead of waiting on hold for hours or getting disconnected. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with was super helpful and confirmed I was taking the right approach with the SS-8 and 8919 forms. She also explained exactly what supporting documentation would strengthen my case and advised me on the timeline. Definitely worth it given how complex misclassification issues are and how much money was at stake.

I have to admit I was completely wrong about Claimyr. After struggling for another week trying to reach the IRS about my misclassification case, I gave in and tried it out of desperation. Within 45 minutes I got a call back and was connected directly to an IRS representative who answered all my questions about Form SS-8 and the misclassification review process. The agent gave me super specific guidance on my situation and confirmed I was right to file both forms. She even explained that the IRS has been cracking down on employee misclassification and gave me pointers on what specific documentation would strengthen my case. Saved me hours of frustration and probably helped me avoid making mistakes that could have delayed my case. For anyone dealing with the misclassification issue like the original poster, don't waste days trying to get through on your own like I did. The peace of mind from speaking directly with an IRS agent about such a complex tax situation was absolutely worth it.

I'm a bookkeeper who's seen this situation many times. One thing to consider that nobody's mentioned yet - check your state labor department too! Many states have their own worker classification enforcement and they often move MUCH faster than the IRS. In some states, filing a misclassification complaint with the state labor department can get you results in weeks rather than months/years with the IRS. Plus state agencies can often force the employer to pay penalties and properly classify you going forward. Another approach if you're still on good terms with either employer: show them the potential penalties they face for misclassification (they can be pretty severe) and ask them to issue W-2s instead of 1099s. Sometimes just educating them about their obligations is enough to fix the problem without involving authorities.

Has anybody here actually gone through the full SS-8 process from filing to determination? Everything I've read online suggests it takes forever to get a ruling. I'm wondering if it's even worth it or if I should just suck it up and pay the self-employment taxes to avoid the hassle?

I'm dealing with a very similar situation right now - got misclassified by an employer who had me working set hours at their location using their equipment, but they issued a 1099 instead of a W-2. The self-employment tax burden is crushing! From what I've researched, you definitely have a strong case for employee classification based on the IRS's common law test. The fact that both employers controlled when, where, and how you worked are major red flags for misclassification. I'd recommend filing the SS-8 and 8919 together rather than waiting. Even though the SS-8 determination takes months, you can use code G on Form 8919 to indicate you're filing it along with an SS-8. This way you only pay the employee portion of Social Security and Medicare taxes (7.65%) instead of the full 15.3% self-employment tax while you wait for the determination. If the IRS rules in your favor on the SS-8 (which sounds likely given your situation), your former employers will be on the hook for their portion of the employment taxes plus penalties. You might even get a refund if you initially paid more than the employee portion. Don't let these employers get away with shifting their tax burden onto you - file those forms and protect yourself!