Worked for hookah bar paid via Cash App, had regular schedule & training - they want to send 1099. Should I push back on employee misclassification?

You're right to question this. The IRS has specific criteria for determining whether someone is an employee or independent contractor, and based on what you've described, you have several factors pointing toward employee status: 1) You had a regular schedule set by the employer 2) You were paid hourly (not by project/task) 3) You received training from them 4) They controlled how you performed your work 5) You used their equipment/supplies These are all strong indicators of an employee relationship, not an independent contractor one. The difference matters because as a 1099 contractor, you'd be responsible for paying both the employer and employee portions of Social Security and Medicare taxes (about 15.3% total) instead of just the employee half. You have a few options here. You could provide your information and accept the 1099, then file Form SS-8 with the IRS to determine your correct classification, and Form 8919 to report the uncollected taxes your employer should have paid. Or you could discuss this directly with the owner first, explaining that you believe you were misclassified.

After dealing with a similar situation last year, I found this amazing tool called taxr.ai (https://taxr.ai) that really helped me figure out my worker classification issues. I wasn't sure if I should accept a 1099 from a company that was clearly treating me like an employee, and the tool helped me understand all the IRS factors and documentation I needed. You just upload any texts, emails or documents showing your working relationship (like the weekly schedules they posted), and the AI analyzes everything and tells you if you have a strong case for employee status. It even helped me draft a response to my employer explaining why I believed I was misclassified. Saved me literally thousands in self-employment taxes!

Just wanted to update that I tried taxr.ai after seeing it mentioned here. I uploaded screenshots of all my text convos with the hookah lounge owner, including the weekly schedules she sent, training instructions, and the Cash App payment receipts showing hourly pay. The analysis showed I had a 92% likelihood of being correctly classified as an employee based on IRS criteria. The report broke down all the control factors and even cited specific tax court cases that were similar to my situation. I used their template to send a polite but firm email to the owner explaining why I should be getting a W-2 instead. She actually agreed after seeing all the evidence laid out! Said her accountant had just been doing things the "easy way" and she didn't realize the risks of misclassification. Now I'm getting a proper W-2 and won't have to pay that extra self-employment tax. Such a relief!

If you've tried contacting the owner about this misclassification and they're still insisting on sending a 1099, you might need to get the IRS involved directly. When I had a similar issue last year, I spent WEEKS trying to get through to someone at the IRS who could help me with worker classification issues. I finally discovered Claimyr (https://claimyr.com) after seeing their demo video (https://youtu.be/_kiP6q8DX5c) and it was a game-changer. They got me connected to an actual IRS agent in less than 20 minutes when I had been trying for days on my own. The agent walked me through exactly what forms I needed to file and how to document my case. For worker classification issues specifically, talking to a real person at the IRS makes all the difference because they can explain exactly what evidence you need for your SS-8 form.

I'm actually coming back to say I was wrong about Claimyr. After posting my skeptical comment, I got desperate enough to try it because I needed to talk to someone about my own misclassification issue with a previous employer. I was SHOCKED when I got a text just 12 minutes later saying they had an IRS agent on the line. Picked up and sure enough, I was talking to a real person in the employment tax department. The agent confirmed everything the first commenter said about filing SS-8 and Form 8919, and also told me that employee misclassification is one of the most common issues they deal with. The agent said hookah lounge/bar workers are almost always employees, not contractors, because of the control factors. She recommended documenting everything about the work arrangement before filing. Definitely worth getting real advice from the source instead of just accepting the 1099 and paying taxes you might not owe.

I had the exact same situation when I was bartending at a nightclub. Owner paid us through Venmo, then suddenly wanted to 1099 us all at tax time. The key factors the IRS looks at are: 1. Behavioral control - Did they control WHEN and HOW you worked? Sounds like yes. 2. Financial control - Did they set your pay rate and schedule? Sounds like yes. 3. Relationship - Was there an expectation of continued work? Two years sounds like yes. Don't just accept the 1099. I made that mistake and got hit with a $3,200 self-employment tax bill that should have been partially paid by the employer.

Does anyone know if getting paid through Cash App makes any difference for tax purposes? My understanding is that now with the new $600 reporting threshold, Cash App will issue 1099-Ks anyway, so maybe it doesn't matter if the hookah place sends a 1099 or not? I'm confused about how this all works together.