Received cash payments from former employer who's now requesting my SSN and address months later - what's going on?

Thanks for the explanation. I'm curious - if the employer does issue a 1099 now, wouldn't that cause problems for the OP since they probably didn't report this income on their taxes last year? Would they need to file an amended return? Also, could the OP face penalties from the IRS for not reporting this income initially?

If the payments were from last year and the person hasn't yet filed their 2024 tax return, they would simply include this income on their regular return due in April 2025. No amendment would be needed in that case. If the payments were from a previous tax year that has already been filed, then yes, they would need to file an amended return (Form 1040-X) to report the additional income. The IRS generally has a 3-year window to assess additional taxes, so it's best to amend proactively rather than waiting for a potential audit notice. Penalties are typically reduced if you voluntarily correct your return rather than having the IRS discover the discrepancy through their matching program.

Does taxr.ai actually help with situations where you don't have official tax documents? I'm in a similar boat but with multiple side gigs that paid me through Venmo. No idea how to report all that income correctly.

I'm skeptical of any service claiming to analyze text messages... How does it actually verify what your employer is doing is legitimate rather than something shady? Couldn't anyone just say they're issuing a tax form when they're really not?

The service helps even without official documents - you can upload payment screenshots, text exchanges, or even just describe your situation. It walks you through identifying what counts as taxable income and how to report it properly, even from places like Venmo or Cash App. For verifying legitimacy, that's a great question. The system analyzes communication patterns and flags unusual requests that don't align with normal tax procedures. It can't guarantee your employer isn't being shady, but it provides context on what's standard practice versus what's suspicious. In my case, it confirmed the timing aligned with tax season obligations and explained what specific information employers legitimately need for 1099 forms.

How does Claimyr actually work? I've tried calling the IRS multiple times and always get the "high call volume" message and get disconnected. Is this service just going to charge me to wait on hold or something?

Yeah right... so they magically get you through when millions of people can't reach the IRS? Sounds like they're just selling false hope. The IRS phone system is fundamentally broken - no service can fix that.

It's not magic - they use a combination of predictive analytics and automated systems to navigate the IRS phone tree and secure a place in line. They monitor hold times and call back when an agent is about to be available. You literally get a text when they're about to connect you to an actual IRS representative. Regarding skepticism, I totally get it. I thought the same thing initially. But their system basically does the waiting for you by monitoring multiple call paths and finding the most efficient route. The IRS phone system is definitely broken, but what Claimyr does is essentially optimize the chaos. My actual conversation with the IRS agent was incredibly helpful for my situation.

Would you recommend the OP ask for a 1099-MISC instead of a 1099-NEC? I've heard the MISC form might have tax advantages in certain situations. Also, does getting a 1099 this late trigger any automatic flags with the IRS?

The employer doesn't really have a choice between 1099-MISC and 1099-NEC for this situation. Since 2020, payments for services performed as a non-employee must be reported on Form 1099-NEC. The 1099-MISC is now used for other types of payments like rent, prizes, medical payments, etc. - not for work performed as an independent contractor. Regarding late filing, it doesn't automatically trigger an audit, but it can raise questions. The employer will likely face penalties for late filing, but that's their problem, not yours. The important thing is that you report the income correctly. Even if you receive the form late, you should still file an accurate return, even if that means amending a previously filed return.

This is such a good point that nobody else mentioned! I got hit with this exact situation and ended up owing like $3,500 in self-employment taxes I wasn't expecting. Is there a way for OP to dispute misclassification without creating a huge problem with the employer?

You can file Form SS-8 with the IRS to request an official determination of worker classification, but that process can take 6+ months. A faster option is to file Form 8919 with your tax return, which lets you pay only the employee portion of FICA taxes while indicating you believe you were misclassified. You'd check the box for "reason code G" (worker received Form 1099-MISC or 1099-NEC but believes they should have received Form W-2). This way you're not ignoring the income, but you're also not accepting the higher tax burden of being incorrectly classified as an independent contractor. The employer would still be responsible for their portion of employment taxes. Just make sure to keep documentation showing you were treated as an employee (set schedule, supervised work, used their equipment, etc.).