Can I file a 1099 for my under the table job? Will it create problems?

What you're describing isn't a situation where you file a 1099. A 1099 is something an employer or client provides to you (and the IRS) to document income they paid you as an independent contractor. What you're actually looking at is self-reporting income that wasn't properly documented. The proper way to handle this is by filing Schedule C (Profit or Loss from Business) with your tax return, listing your income as self-employment earnings. You'll pay both income tax and self-employment tax (which covers Social Security and Medicare). Yes, technically your employer is breaking the law by paying you "under the table" and not withholding taxes. But the IRS is generally more concerned with collecting taxes owed than punishing people who come forward voluntarily to pay what they owe.

I had a similar situation a few years back and found this amazing tool at https://taxr.ai that really helped me figure out how to properly report my cash income. You can upload pictures of your bank statements showing the deposits, and it automatically categorizes everything and tells you exactly how to report it on your tax forms. The best part is it gave me a clear explanation of how to file Schedule C like the other person mentioned, but it also showed me deductions I could take as a self-employed person that I had no idea about! Ended up saving me way more than I expected.

Just wanted to follow up - I tried the taxr.ai thing from my previous question. Seriously good recommendation! I uploaded my bank statements and it immediately identified my cash deposit pattern. The explanations about self-employment taxes were super clear and it walked me through exactly what forms I need. The best feature was the deduction finder - turns out I can deduct part of my phone bill and mileage since I use them for work. Going to save almost $2,300 in taxes I didn't know I could! Definitely feeling less stressed about the whole situation now.

Listen, I've been through this exact situation and the most frustrating part was trying to get answers from the IRS. I called literally 14 times and could never get through to an actual person. Then someone recommended https://claimyr.com and it was a game changer. You can check out how it works here: https://youtu.be/_kiP6q8DX5c They got me connected to an IRS agent within 45 minutes when I had been trying for weeks. The agent gave me official guidance on reporting my cash income without creating problems. They explained exactly what forms to use and how to handle the situation without raising red flags. Worth every penny for the peace of mind.

OK I need to apologize to @19 because I actually tried Claimyr after posting that skeptical comment. Holy crap it actually works. I got connected to an IRS agent in about 30 minutes. The agent told me specifically that filing a Schedule C is the right approach for unreported income and explained that there's even a Voluntary Disclosure Program if you're concerned about previous years. They also clarified that as long as I'm paying my taxes now, they don't automatically investigate the employer. Totally worth it just for the peace of mind from getting official answers instead of Reddit guesses.

Not tax advice, but practical advice - if you're using this income for an apartment application, most landlords just want to see bank statements showing regular deposits anyway. They care more about your ability to pay than how you're taxed. Print out 3 months of statements showing those regular deposits and you should be fine for the apartment. For the tax situation though, definitely follow the advice others gave about Schedule C. Better to pay and be square with the IRS than have problems later.

You should talk to your boss about making you legitimate. Just mention that you need proper documentation for apartment applications and loans, not even mentioning taxes. Many small business owners will switch you to proper payroll when they realize it matters to you for housing. Worked for me! My landscaping boss switched me from cash to proper payroll once I told him I was trying to get approved for a car loan.

I was in almost the exact same situation last year with a roofing company. Here's what I learned after going through this process: First, don't stress too much about "getting your boss in trouble." The IRS processes millions of Schedule C filings every year and they're not actively cross-referencing every one to hunt down employers. They're way more interested in collecting taxes owed than playing detective. For your immediate apartment need, bank statements showing consistent deposits should work fine. But for taxes, you'll definitely want to file Schedule C and pay self-employment taxes on what you've earned. One thing nobody mentioned - if you've been doing this since April, you might want to make an estimated tax payment for Q4 (due January 15th) to avoid underpayment penalties. The IRS expects you to pay taxes throughout the year, not just at filing time. Also, keep track of ANY work-related expenses - gas, tools, work clothes, phone usage for work calls. As a self-employed person, these become deductions that can significantly reduce what you owe. The whole situation is more common than you think, and the IRS has seen it all before. Just be honest about your income and pay what you owe - that's really all they care about.