I didn't use a payroll service last year, which is probably why I'm in this mess now! Do you know if these services can help with fixing past mistakes if I wasn't using them before? Or is it too late?

They can definitely help with past mistakes even if you weren't using them before! Both Homepay and SurePayroll offer "catch up" services where they'll help you file the missing forms from previous years. You'll need to provide them with the payment information for your household employee from 2023, and they can generate the proper W2 and W3 forms. They usually charge a one-time fee for this service rather than making you sign up for ongoing payroll. It's totally worth considering if you want to make sure everything gets done correctly without having to learn all the details yourself.

This is really important advice. I accidentally used the wrong year form once and it was a nightmare to fix. Another tip - keep copies of EVERYTHING you send to the SSA. I had to reference my copies when there was a mix-up with my household employee's Social Security earnings.

Do you have to create an account with the IRS to use their free fillable forms for the extension? And is it actually free or do they try to upsell you?

You do need to create an account on the Free File Fillable Forms site, but it's pretty straightforward. It's completely free with no upsells - it's the official IRS program. It's basically just the raw forms without any guidance, so the extension form (4868) is simple enough, but some people find the complete tax forms overwhelming without software guidance. For just the extension though, it's a great free option.

Yeah, filing an extension will definitely delay your refund since the IRS won't process your actual return until you submit it. The extension just gives you more time to file the paperwork, but your refund won't be processed until after you submit your complete return.

But wouldn't that mean you're artificially inflating your income and then taking deductions against it? I feel like that's not accurately representing what's happening - these ARE reimbursements, not actual income.

You're right that it's not the most accurate representation of what's happening. It's more of a pragmatic workaround when dealing with clients who won't issue proper 1099s. The end result tax-wise should be roughly the same for most expenses except meals. For meals, you'd still be limited by the 50% rule, which is the original problem. So this approach works better if meal expenses are a small portion of your reimbursements.

This is by far the best solution if the client will do it. I've been freelancing for 15 years and this is what all my long-term clients do now - they book travel directly and either pay for meals directly or give me a per diem. Makes taxes WAY simpler.

Thank you for this perspective. Could you clarify about the FMLA part? I thought that only applied to companies with 50+ employees, and we only have 9 total. Are there similar protections for smaller businesses?

You're absolutely right about FMLA - it only applies to companies with 50+ employees, so your company is too small to be required to provide that protection. I should have been more clear. However, many states have enacted their own family leave laws that extend to smaller businesses. Depending on where you live, there might be state-specific protections even though you're not covered by federal FMLA. For example, some states require even small employers to provide job protection and/or paid leave. That's definitely worth looking into based on your specific location.

The fraud part is the intentional misrepresentation. If they're specifically timing a "layoff" to coincide with maternity leave and have already promised to bring her back at a specific date, that's not a true layoff - it's a planned temporary absence that they're trying to disguise as a layoff to shift costs to the state. A legitimate layoff would be based solely on business needs, not timed specifically to coincide with a planned medical event, and wouldn't come with a guaranteed rehire date.

What exactly happens if you can't get someone to fill out a W-9? Like if they refuse or you just can't reach them anymore? Are you still supposed to issue the 1099 somehow?

If someone refuses to complete a W-9 or you can't reach them after payment, you're technically supposed to begin backup withholding at a rate of 24% on any future payments to that person. This means holding back that percentage and remitting it to the IRS. For the 1099-NEC, you should still issue it with whatever information you do have. If you're missing their tax ID number, the IRS may send you a B-notice requesting the missing information. The best protection is documenting your attempts to get their information (emails, certified letters, etc.). The IRS understands these situations happen, but they want to see you made a good faith effort to comply.

So what's the actual difference then? Like how much control can you have before they're considered an employee? I sometimes need people to be at certain places at certain times because, you know, that's when the client expects us.