I've been following this thread and wanted to add my perspective as someone who went through a very similar situation. The "wait and report after leaving" strategy mentioned by others is actually quite effective, but I'd also suggest documenting everything NOW while you're still there. Start keeping detailed records of: your work schedule, any emails showing you're required to be in the office, descriptions of your ongoing duties vs. project-based work, and any communications about your employment status. Take screenshots of job postings if they advertised your position differently than how you're classified. This documentation will be crucial whether you decide to approach your employer directly, file with the IRS, or report after finding a new job. I made the mistake of not documenting enough in my situation, and it made proving my case much harder later. Also, consider checking if your company has an HR department or if decisions are made by one person. Sometimes the person doing payroll doesn't fully understand classification rules, and bringing it to HR's attention (framed as a compliance question) might resolve it without drama. But definitely have that documentation ready first, just in case.

One thing I haven't seen mentioned here is checking if your company has any policies or employee handbook that might inadvertently contradict your contractor classification. Many employers slip up by including 1099 workers in employee-only policies or expecting them to follow the same rules as W-2 staff. Also, since you mentioned the other admin has been there 12 years, that's actually a huge red flag for the IRS. Long-term "contractor" relationships, especially for ongoing administrative work, are classic misclassification cases. The IRS specifically looks for situations where someone performs the same role for years as evidence of an employer-employee relationship rather than true independent contracting. You might want to research what happened to other companies in your industry who got caught doing this. Sometimes showing your employer news articles about similar businesses facing penalties can be more persuasive than citing IRS regulations directly. It makes the risk feel more real and immediate. And honestly, given that you're new and they've been misclassifying the other admin for over a decade, this company is probably sitting on a pretty significant tax liability if the IRS ever investigates. That might actually work in your favor if you do decide to have a direct conversation about reclassification.

Can someone explain the difference between 1099-NEC and 1099-MISC? I thought I needed a MISC form but now I'm confused seeing this post. I do freelance graphic design if that helps.

I was in almost the exact same situation when I started my consulting business! Living at a friend's place with no formal lease or utilities in my name. I stressed about this way more than I needed to. The bottom line is that the IRS just needs a reliable mailing address where they can reach you. It doesn't matter whose name is on the lease or utilities. I've been using my friend's address for over two years now with zero issues. Just make sure your cousin is cool with receiving business mail there, and maybe give them a heads up about what types of documents might arrive (1099s, tax notices, etc.). One tip: be consistent with whatever address you use across all your tax documents and business registrations. The IRS cares way more about consistency than they do about proving you "own" the address. Good luck with your new business!

One thing nobody has mentioned - if you have proof that your ex knowingly claimed your child incorrectly (like text messages where he admits it), you should consider reporting him for tax fraud using Form 3949-A. The IRS takes this stuff seriously, especially if there's a pattern.

I'm so sorry you're dealing with this - it's incredibly frustrating when an ex tries to pull something like this! As others have mentioned, you're absolutely in the right here. Since you have full custody, you're the custodial parent and entitled to claim your daughter. I'd recommend filing your paper return ASAP and including a clear cover letter explaining that you're the custodial parent with full legal and physical custody. Attach copies of your custody agreement (highlight the relevant sections), school enrollment records showing your address, and any medical records that show you as the primary contact. The more documentation you provide upfront, the smoother the process will be. One tip that helped me when I dealt with IRS paperwork - send everything certified mail with return receipt so you have proof of delivery and timing. Keep copies of everything you send. The waiting is the worst part, but stay strong! The IRS will sort this out correctly, and your ex will likely think twice about trying this again once he realizes the consequences. Focus on documenting everything properly and let the system work - you've got this!

I've been following this thread closely as I'm in a similar situation with employer-paid disability premiums. One thing I wanted to add that might help others - if you're still unsure about your specific situation after reviewing your plan documents, you can also request a written clarification from your benefits administrator or payroll department. I did this last year when I couldn't determine from my paystub whether the premiums were being treated as taxable income. I sent a simple email asking: "Are the disability insurance premiums paid by the company included in my taxable wages, and if so, in what amount?" They responded with the exact dollar amounts and confirmed the tax treatment. This documentation became really valuable when I was preparing my taxes, and it also helped me understand that I had the option to change my election during the next open enrollment period. Sometimes the most direct approach - just asking your employer's benefits team - can save a lot of confusion and research time. The key is asking for the information in writing so you have it for your tax records, rather than relying on a verbal explanation that you might misremember later.

As a newcomer to this discussion, I'm really grateful for all the detailed explanations here! I'm dealing with a similar situation where I just started a new job that offers disability insurance, and I had no idea there were different tax treatments depending on how the premiums are structured. One question I have after reading through all these responses - if my employer gives me the choice between having them pay the premiums (making future benefits taxable) versus having the premiums deducted from my after-tax pay (making future benefits tax-free), how do I decide which option is better? Is there a rule of thumb for evaluating whether it's better to pay tax on the smaller premium amount now versus potentially paying tax on larger benefit payments later if I ever become disabled? I imagine it depends on factors like my current tax bracket, expected future tax rates, and the likelihood of actually needing the benefits, but I'm not sure how to weigh all of that. This thread has already taught me so much about disability insurance taxation that I never knew before!

16 I'm in the exact same situation and my accountant advised something different than what others are saying here. He told me that since I own more than 2% of the S-Corp, health insurance has to be handled as additional compensation on my W-2, then I deduct it as self-employed health insurance on my personal taxes. He said S-Corps can't use QSEHRA for owners with >2% ownership. Is this right??

As someone who's been through this exact scenario, I can confirm what others have mentioned about the >2% shareholder rules. The key thing to remember is that even though the reimbursements have to go through your W-2 as taxable wages, you still get the tax benefit through the self-employed health insurance deduction on Line 16 of Schedule 1. One thing I'd add that hasn't been mentioned - make sure you keep detailed records of the actual premium amounts your spouse's employer deducts from their paychecks. The IRS may want to see that the reimbursements from your S-Corp don't exceed the actual premiums paid. Also, the reimbursement timing matters - you generally need to reimburse in the same tax year the premiums were paid. The formal plan documentation is absolutely critical. I learned this when helping a friend who got audited - the IRS disallowed all their health insurance deductions because they couldn't produce the required corporate resolutions and plan documents, even though they had been reporting everything correctly on their tax returns.