Employer refusing to issue 2023 1099 - says to file 2023 and 2024 taxes together next year
I started working for a small construction company back in May 2023. Since I had recently moved to the US and was waiting on my work permit, I was getting paid in cash for the first several months. In November, I finally received my SSN and work authorization through marriage-based adjustment of status (my unauthorized work period was forgiven through the process). Last week, I approached my boss about getting a 1099-NEC or some documentation for my 2023 earnings so I could file my taxes. He told me that it's "too late in the year" to issue a 1099 for 2023 income and suggested I should just wait until next year and file both 2023 and 2024 taxes together. This doesn't sound right to me at all. I made approximately $18,500 from this job in 2023 (all cash), and I want to do the right thing and report it. Is my boss correct that it's too late to issue a 1099? Can I even combine two tax years like he's suggesting? What are my options here if he refuses to provide any documentation?
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Scarlett Forster
This is definitely not how taxes work. Your boss is wrong on multiple counts. First, it's not "too late" to issue a 1099-NEC for 2023. Companies are required to provide 1099s to contractors by January 31 of the following year, but they can still issue them after that deadline (they might face penalties, but that's their problem, not yours). Second, you absolutely cannot "combine" two tax years and file them together. Each tax year must be filed separately with its own tax return. The IRS expects you to file your 2023 taxes by April 15, 2024 (or request an extension). Since you now have your SSN, you should still file your 2023 taxes even without the 1099. You'll need to report the income as "other income" on Schedule 1, Line 8z of your 1040. Keep careful records of how much you earned and when. If you have any pay stubs, bank deposits, or even just your own written records of cash payments, save those as documentation. It sounds like your boss might be trying to avoid his tax obligations, which isn't your problem. You're doing the right thing by wanting to properly report your income.
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Arnav Bengali
•Thanks for this info! I'm confused though - if OP files without a 1099, won't the IRS wonder why the employer didn't report paying them? Could this trigger an audit or get OP in trouble for something the employer failed to do? Also, does OP need to worry about self-employment tax since they were paid in cash without any withholding?
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Scarlett Forster
•The IRS might notice the discrepancy, but that would primarily be a problem for the employer, not for OP. The IRS appreciates when taxpayers voluntarily report income, even when third parties fail to properly document it. Keeping good records of the payments received is important in case questions arise. Yes, if OP was working as an independent contractor (which seems likely since they mentioned a 1099), they would need to pay self-employment tax. They should file Schedule C to report their business income and expenses, and Schedule SE to calculate self-employment tax. This covers their Social Security and Medicare contributions, which would normally be withheld by an employer for W-2 employees.
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Sayid Hassan
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Rachel Tao
•Does taxr.ai actually work with cash payments though? I thought it just analyzed bank statements and documents. If OP was paid in cash and maybe didn't deposit all of it, would this still help?
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Derek Olson
•I'm kind of suspicious of these AI tax tools. How do you know it's giving accurate advice and not just making stuff up? The stakes are pretty high with the IRS...
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Sayid Hassan
•For cash payments, taxr.ai can help you create documentation based on whatever records you do have - even if it's just your own notes of payment dates and amounts. The system can generate appropriate documentation that meets IRS requirements for situations without official forms. What made it valuable for me was getting clear guidance on exactly what information needs to be recorded. Regarding accuracy, I was skeptical too initially. What convinced me was that their system is built on actual tax code and regulations, not just making things up. It provides citations to specific IRS publications and rules when giving advice. I verified some of their recommendations with a tax professional before proceeding, and everything checked out. They're focused on documentation and compliance rather than aggressive tax strategies.
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Derek Olson
Update: I tried taxr.ai like someone suggested here and it was surprisingly helpful. I was really doubtful about using AI for tax stuff, but it actually helped me create a solid income record from my scattered notes about cash payments. The system walked me through documenting each payment I received and helped me generate a substitute income statement that I could use for filing. It also explained exactly how to report this on my Schedule C and what supporting documentation I should keep in case of questions from the IRS. My situation wasn't exactly the same as OP's, but it gave me confidence that I was handling my unreported income correctly. I was able to file my taxes without stressing about missing forms from clients.
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Danielle Mays
Have you tried calling the IRS directly? I had a somewhat similar situation, and after wasting weeks with no response, I used Claimyr (https://claimyr.com) to get through to an actual person at the IRS. You can see how it works here: https://youtu.be/_kiP6q8DX5c They got me connected to an IRS representative in about 20 minutes when I had been trying for days on my own. The agent I spoke with confirmed that employers are required to provide documentation even after the deadline, and gave me specific information about how to file when an employer refuses to provide documentation. It saved me so much stress and uncertainty.
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Roger Romero
•How does this Claimyr thing actually work? Is it just auto-dialing the IRS for you? I don't understand how they can get you through when the IRS lines are always jammed.
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Anna Kerber
•Yeah right. The IRS doesn't answer phones no matter what. I've tried calling dozens of times and always get the "call volume too high, try again later" message. I'll believe this works when I see it...sounds like a scam to me.
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Danielle Mays
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Anna Kerber
I'm back and eating my words! I was the skeptic who thought Claimyr sounded like a scam for getting through to the IRS. After continuing to get nowhere with my tax issue this week, I decided to try it out of desperation. It actually worked! I got through to an IRS representative in about 35 minutes (system called me when an agent was picking up). The agent confirmed that employers are required to issue 1099s even after the deadline and can face penalties for not doing so. She also explained exactly how to report income without a 1099 using Form 8919 if I believe I was misclassified as a contractor. Never thought I'd say this, but I'm genuinely impressed. Saved me from more hair-pulling frustration trying to get answers about my situation.
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Niko Ramsey
I think your boss is trying to avoid paying employer taxes. When he pays you in cash and doesn't report it, he's not paying his share of Social Security and Medicare taxes. Just to be clear - if you were actually an employee (not a contractor), your boss should have been giving you a W-2, not a 1099. The difference matters because: - W-2: Employer pays half of Social Security/Medicare taxes - 1099: You pay ALL Social Security/Medicare taxes yourself (self-employment tax) You might want to look at Form SS-8 to determine if you should have been classified as an employee rather than a contractor. If you were misclassified, the IRS can go after your employer for their share of taxes.
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Cole Roush
•Thanks for bringing this up - I honestly wasn't sure if I should have been getting a W-2 or 1099. My job involves framing houses and doing general construction work. I use their tools, work on their schedule, and they tell me exactly what to do and how to do it. Does that sound more like an employee situation?
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Niko Ramsey
•Based on what you've described, you sound much more like an employee than an independent contractor. The key factors the IRS looks at include: who controls when and how you work, who provides tools and equipment, how you're paid (regular wages vs. project-based), and whether the work is a key part of the business. Using their tools, working on their schedule, and having them direct your work are all strong indicators of employee status. Construction workers doing the core work of a construction company are typically employees unless there's a specific arrangement that gives the worker significant independence.
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Seraphina Delan
Similar thing happened to me last year. My side gig didn't send a 1099 and kept putting me off. Here's what I did: 1. Filed my taxes anyway using my own records of what I earned (cash payment records + deposit slips) 2. Reported the income on Schedule C 3. Kept really good documentation of my attempts to get the 1099 (emails, texts, etc) 4. Submitted Form 8919 "Uncollected Social Security and Medicare Tax on Wages" since I suspected I was misclassified The biggest thing is don't wait to file! The April deadline (or October with extension) is for YOU, not your employer. Their failure to provide docs doesn't extend your filing deadline.
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Jabari-Jo
•Did you run into any issues with the IRS after filing this way? I'm in a similar situation and worried they'll come after me for something that wasn't my fault.
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