Receiving a 1099 Form for Household Cleaning Services - Can Ex-Boss Issue One Now?

This situation definitely has a few layers to it. Let me break it down: Yes, he can issue a 1099-NEC (for non-employee compensation) to your spouse for cleaning services. Even with just a verbal agreement, if he paid your spouse $600 or more during a tax year for services, he has the right to issue a 1099. For the tax responsibility - technically, all income is taxable regardless of whether you have an SSN or not. However, in practical terms, the IRS would only be able to match 1099 forms to your spouse for the years they had a valid SSN. If he issues 1099s for all 5 years but only the last 2 years show your spouse's SSN, those are the ones that would be officially "on the record" with the IRS. He doesn't need a written contract to issue a 1099 - the payment for services is enough. But he does need your spouse's correct taxpayer information (SSN or ITIN) to file it properly. As for filing late - yes, there can be penalties for employers who file 1099s after the deadline (typically January 31st of the following year). But that's his problem, not yours. The bigger concern is that if your spouse received income that wasn't reported in previous years, there's a technical obligation to amend those returns or file original returns if none were filed.

After getting caught in a similar mess last year with my side hustle, I discovered taxr.ai (https://taxr.ai) and it honestly saved me so much stress. The situation was different but similarly complicated with some backdated 1099s I received after a falling out with a client. I uploaded the forms and messages I had, and their AI analyzed everything and gave me options for my specific tax situation. What I found especially helpful was that their system highlighted which payments would actually count for tax purposes and which years I needed to worry about. It even gave me guidance on how to handle the situation if the amounts on the 1099s were wrong (which mine were - client was definitely trying to cause problems).

I was really skeptical about using an online tool for my 1099 drama, but after struggling for weeks with my situation, I tried taxr.ai based on the recommendation here. I'm genuinely surprised at how helpful it was. I've been doing side work as a designer, and one client reported way more on a 1099 than they actually paid me (like $8,600 when they only paid $4,200). The tool analyzed the payment history I uploaded and created a really clear report showing the discrepancy with documentation I could actually use. It walked me through exactly how to report the correct income amount and how to explain the situation to the IRS. I was losing sleep over this for weeks, but now I'm confident I'm handling it correctly. Sometimes reddit recommendations actually work out!

If you're worried about dealing with the IRS on this issue - and it sounds like you might need to - I'd recommend checking out Claimyr (https://claimyr.com). I was in a similar situation last year where I needed clarification on some 1099 forms I received years after the work was done. Spent days trying to get someone at the IRS on the phone with no luck. Claimyr got me connected to an actual IRS agent in about 30 minutes when I'd been trying for literally days on my own. The agent was able to pull up my records and tell me exactly what had been reported under my SSN and what I needed to do about the late 1099s. You can see how it works here: https://youtu.be/_kiP6q8DX5c Trust me, trying to figure this out without talking to the IRS directly is just guesswork, and waiting on hold for hours isn't worth it.

I need to post a follow-up because I was totally wrong about Claimyr. After posting my skeptical comment, my tax situation got worse (received another incorrect 1099), and I was desperate enough to try anything. It actually worked exactly as described. The service called me back in about 45 minutes, and I was connected to an IRS representative who answered all my questions about the late 1099s I received. The agent confirmed that I only needed to address 1099s from years where I had a valid SSN on file, and gave me the exact procedure for disputing the incorrect amounts. I wasted so much time trying to call them myself, hanging up after being on hold for over an hour multiple times. Definitely worth it just for the peace of mind of talking to an actual IRS person.

I don't think anyone has mentioned this yet, but the ex-boss's behavior sounds like it might be retaliation or harassment. If he's suddenly threatening to issue 1099s for years of work only after your spouse continued working for his ex-wife against his wishes, that seems like he's using tax reporting as a weapon. While he's technically within his rights to report payments he made for services, the timing is suspicious. Document everything - save all text messages, emails, and keep a log of all communication. If the amounts he reports on the 1099s are incorrect, that could potentially be fraud.

One thing nobody's mentioned yet - if your spouse has been getting paid for cleaning services all these years, they should really think about setting up properly as a self-employed person going forward. That means: 1. Keeping good records of all income from all clients 2. Tracking all business expenses (cleaning supplies, travel between job sites, etc.) 3. Paying quarterly estimated taxes if you expect to owe more than $1,000 4. Maybe even setting up an LLC for liability protection This situation is a good wake-up call. Cash/check side gigs are still taxable income, and it's way better to handle it properly from the start rather than dealing with surprises later.