That's weird, my 401k is through Vanguard and they literally just had me check a box saying I qualified under the CARES Act. No documentation required at all. I wonder if different companies have different policies?

Yes, each 401k administrator sets their own verification policies. Fidelity was being extra cautious with my company's plan, but Vanguard and others often just require the checkbox as you mentioned. It varies widely by both the administrator and sometimes even by the specific employer's plan. The actual IRS guidelines only require self-certification, but plan administrators can add their own layer of verification if they choose to. Always best to check directly with your specific plan before proceeding.

Wait seriously? I thought the CARES Act provisions were extended! This completely changes things for me. So there's no special COVID-related withdrawal option for 401ks anymore?

That's mostly correct, but there's a small caveat. While the general CARES Act withdrawal deadline was December 30, 2020, some COVID-related relief provisions were extended through other legislation. However, the specific 401k withdrawal provisions with penalty waivers and extended repayment options did indeed expire.

Thanks for bringing this up! I had no idea about the itemizing rule. Does this mean we need to coordinate our filing strategies even if we're doing separate returns? That seems frustrating.

Yes, you do need to coordinate at least on this one aspect. If your ex decides to itemize their deductions, you'll be forced to itemize as well, even if your itemized deductions are less than the standard deduction. This can result in you paying more tax than if you both took the standard deduction. It's one of the downsides of the Married Filing Separately status. That's why it's worth having a brief conversation with your ex about whether either of you plans to itemize, just so you're not caught off guard.

No, you can't claim Head of Household if you're married as of December 31st. You would need to be "considered unmarried" which means either legally separated under a decree or legally divorced. Plus you need a qualifying dependent and to have paid more than half the cost of keeping up your home.

That's really helpful! I'm in Illinois - do you know if they're pretty good about this kind of thing? I've never filed any kind of complaint before.

Illinois actually has a pretty strong stance on worker misclassification! They have a specific task force called the Illinois Task Force on Misclassification that investigates these exact situations. You can file a complaint through the Illinois Department of Labor. The state takes these issues seriously because misclassification costs them tax revenue and deprives workers of benefits and protections. The complaint process is straightforward - you'll need to provide information about the company, your working arrangement, and copies of any documentation you have (pay stubs, text messages about scheduling, etc). Even without recorded conversations, your description of the working relationship can be enough for them to investigate.

This! When I was a house cleaner, I tracked my mileage between client houses (NOT from home to first job or last job to home, that's commuting), and all my supplies. Reduced my taxable income by almost 40%. Even if you didn't track it at the time, you can reconstruct reasonable estimates with calendar entries, texts arranging jobs, etc.

Omg I didn't even think about the insurance subsidies! Do you know if there's a limit to how much they can make you repay for those? I've been getting pretty substantial subsidies since my individual income is low...

There are repayment limitations based on your household income as a percentage of the federal poverty level. For most people, the maximum repayment amount ranges from $325 to $2,700 per year depending on income level. However, if the amended return pushes your household income above 400% of the federal poverty level, there is no repayment cap - you'd have to repay ALL subsidies received. This threshold is what really hurt in my situation.

This is so confusing! I thought if you paid your own tuition you always claim your own education credits regardless of dependency status? My parents claimed me but I still claimed my own American Opportunity Credit last year.

Thanks for the tip about the Interactive Tax Assistant! I'm definitely going to check that out before making any decisions. I didn't realize grandma could claim the education credits if she claims me - that could be a significant benefit since I have about $12,000 in tuition expenses each year.

Yeah I did get a confirmation email from TurboTax when I made the payment, but it was just saying they submitted it - not that the IRS actually received it. Should I be getting something directly from the IRS too?

Yes, you should have received a confirmation directly from the payment processor the IRS uses, not just from TurboTax. When you pay through TurboTax, they typically redirect you to an IRS-authorized payment processor, which should provide its own confirmation number. I'd recommend logging into your TurboTax account and checking the payment details section. There should be information about how your payment was processed and possibly a second confirmation number from the actual payment processor. If you can't find this, you might want to contact TurboTax support to get the payment confirmation details.

This is the right answer. I check my transcript every year. The transaction codes tell you everything - way more reliable than calling or using Where's My Refund.

Thanks! Yeah I've found the transcript to be the most reliable source of information. The IRS website isn't the most user-friendly, but once you learn how to read the transaction codes, it's actually pretty straightforward. For anyone looking for this information, you want the "Account Transcript" specifically, not the "Return Transcript" - they're different documents in the IRS system.