Does the IRS Free File Fillable Forms have any income limits? I make around $85k and often get locked out of the "free" options.

The Free File Fillable Forms have no income limits at all - they're available to everyone regardless of income. That's different from the IRS Free File Program partners (like TurboTax Free File, etc.) which typically have a $73,000 income limit. The trade-off is that Fillable Forms provide no guidance or calculations - you're basically just filling in digital versions of the paper forms. You need to know which forms to complete and how to do the calculations yourself. Form 8880 for the Retirement Savings Credit isn't terribly complicated though, especially if you're just claiming for yourself and spouse.

The 2023 income limits are actually a bit higher now: $73,000 for married filing jointly and $36,500 for singles (full phase-out points). But yes, checking if you're truly eligible is important!

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.

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.

That's a good point about businesses relocating. I hadn't considered that angle. Are there any states that actually do use origin-based sales tax for online sales? Or is destination-based pretty much the standard everywhere now?

Only a handful of states use origin-based sourcing, and they typically only do so for intrastate sales (sales within the state). Texas and Ohio have elements of origin-based sourcing for sales within their states, but they still use destination-based for interstate sales. For interstate commerce (selling across state lines), destination-based is now the standard across the US. The Streamlined Sales and Use Tax Agreement (SSUTA) that about half the states have joined is built around destination-based principles to create more uniformity. Unfortunately, major states like California, New York, and Texas haven't joined SSUTA, which is why we still have so much complexity.

I wouldn't recommend intentionally ignoring tax obligations, but realistically many states have enforcement thresholds. They're typically focusing audit resources on larger sellers. That said, the risk is that states can come after you for back taxes, penalties and interest years later if they do catch you.

Oh that's a really helpful way to check! I'm going to look at the numbers again tonight. If I take her total RSU value that vested throughout the year and subtract the "stock offset" amount, that should roughly equal the taxes withheld on the RSUs. I'll see if that math works out. Thanks for the tip!

Glad that helps! One other thing to check is her brokerage account statements. The number of shares she actually received multiplied by the vesting price should roughly equal the "stock offset" amount. There might be some small discrepancies due to rounding or timing, but they should be close. Many companies also provide an equity compensation portal or statements that break down each RSU vest event with the price, shares sold for taxes, and net shares delivered. Comparing those statements with her paystubs can give you the complete picture of how everything is being reported.

Does regular TurboTax handle this or do you need the Premier version specifically? I've been using the Deluxe version for years but now I'm getting RSUs and wondering if I need to upgrade.