I honestly hadn't considered that angle! I was briefly part of a small partnership about 6 years ago that dissolved, but we remained on good terms. I never thought they might still be using my info for something, but I'll definitely reach out to my former partner to check. That said, I'd still expect the IRS to be able to tell me who's making these payments. It's bizarre that they claim they can't see the source when it's their own payment system.

Glad I could suggest something helpful! The IRS systems are surprisingly disconnected from each other. The department that processes payments often doesn't have access to the details of who submitted them, especially for third-party payments. When you talk to your former partner, ask specifically if their accountant might be making these payments. In my case, the accountant had set up an automated system years earlier and nobody thought to update it after our business relationship ended. Definitely check on that possibility before going through all the hassle with the IRS.

This is good advice. I work in tax preparation, and I've seen several cases where the IRS corrected errors years later and then demanded repayment with interest and penalties. Document everything and maybe consider putting those refund amounts into a separate savings account so you have the money available if they ever come asking for it.

Can you explain more about the QSBS angle? I've heard it mentioned before but don't fully understand how it works with ISOs or if there are timing considerations.

QSBS (Qualified Small Business Stock) is a potentially huge tax benefit that allows you to exclude up to 100% of capital gains when you sell qualifying stock (up to $10M or 10x your basis, whichever is greater). For it to qualify, you need to: 1) Acquire stock directly from a C-Corporation with less than $50M in gross assets when issued 2) Hold the stock for at least 5 years 3) The company must be in an active qualifying business (most tech companies qualify, but some industries like hospitality or finance are excluded) With ISOs, the timing matters because QSBS status is determined when you exercise, not when you're granted options. So exercising early while the company is still small enough could secure QSBS treatment, even if it grows beyond $50M in assets later. This is a major reason some people exercise underwater options - the potential long-term tax benefit can far outweigh the immediate cost.

Ouch, that's brutal. Did you at least get to carry forward the losses to future years? I thought capital losses could be carried forward indefinitely.

Wait so I should use different software for the current year vs previous years? I'm trying to understand the process of catching up.

You can use the same software for all years, but you'll need to file each year separately. Most tax software has options for filing prior years. You'll just need to make sure you're using the correct forms for each tax year. When you start the process, you'll usually see an option like "File 2024 taxes" or "File for a previous year." You would need to go through the whole process once for each year (2022, 2023, 2024). Just make sure you have the W-2 forms for each corresponding year since the numbers will be different.

The normal deadline is April 15th each year for the previous year's taxes (so April 15, 2025 for your 2024 taxes). But if you're owed a refund, you actually have 3 years to file before you lose the money. So right now in 2025, you could still file for 2022, 2023, and 2024. If you owe money instead of getting a refund, then filing late can result in penalties. But since you're just starting out and probably don't make a ton of money, it's very likely you'll get refunds.

This happened to my brother! His construction job gave him a weird W2 that was mostly empty and later claimed he was "1099" but never gave him an actual 1099. He had to pay all the taxes himself and it was a nightmare.

Thanks for this insight. Our pediatrician has actually written respite care into my daughter's care plan, but nothing specifically about who provides it. Would it help if we got the doctor to write a letter specifically mentioning that having a trusted family member like grandma is beneficial for our daughter's condition since she struggles with new people due to her autism?

Yes, that would definitely strengthen your case considerably. Having your pediatrician specifically document that a familiar caregiver like your daughter's grandmother is medically beneficial due to her autism-related difficulties with new people would create a direct medical necessity connection. The letter should explain why this specific arrangement (flying in grandmother) is medically necessary rather than just convenient or preferable. Make sure the letter mentions your daughter's diagnosis, why consistent caregivers are important for her condition specifically, and how this respite care benefits her medical condition beyond just giving you a break.

I used TaxSlayer last year for a similar situation with my son's therapy travel expenses. TurboTax was too limiting for our complex medical situation. TaxSlayer has a specific section for unusual medical expenses where you can add detailed notes explaining the medical necessity.