Doesn't that mean you have to pay for the tax software twice? Once for the estimate and once for actually filing?

No, you don't have to pay twice. With most tax software, you only pay when you actually file. You can go through the entire process, see your refund amount, and then just save your progress. When you're ready to file for real, you just pick up where you left off and submit. Some software even lets you create multiple scenarios without charging you. I've done this with TurboTax where I tried different filing statuses to see which gave a better refund before deciding which one to actually use.

Free File is great in theory but sometimes those "free" options hit you with fees at the last minute for state filing or certain forms.

Thanks for that tip about the adjustment code! I didn't even know I had to indicate why I was changing the basis. How detailed do I need to be with the explanation? Is it enough to just say "RSU vesting date FMV" or do I need to provide more documentation?

Code "B" is all you need on Form 8949 - you don't need to write a detailed explanation. However, I highly recommend keeping documentation that shows the fair market value on the vesting date. This could be your vesting statements, pay stubs showing the RSU income, or a statement from your company's equity portal. If you get audited (which is unlikely but possible), having that documentation ready will make the process much smoother. The IRS mainly wants to ensure you're not double-counting the income (once when it vested and again when you sold), or trying to avoid taxes by artificially increasing your basis.

You should definitely use the Supplemental Information! That's actually the correct data for your tax return. The official 1099-B often shows zero basis because that's what brokerages are required to report to the IRS, but the Supplemental Information shows the actual cost basis you should use. This is a really common issue with RSUs. The brokerage knows you need the adjusted basis information but they can't put it on the official 1099-B form due to IRS reporting requirements. That's why they provide it separately.

But what if the numbers on the paystub don't match what should've been on the W-2? Can you get in trouble for that? Who's responsible if there's a discrepancy?

If there's a discrepancy between your pay stub and what would have been on your W-2, you won't get in trouble as long as you're using the best information available to you and documenting your efforts to get the correct information. The responsibility ultimately falls on the employer to provide accurate tax documents, and the IRS understands that sometimes taxpayers have to file with estimated information. When you file Form 4852, there's actually a section where you explain how you determined the amounts and what efforts you made to obtain the correct W-2.

Did anything actually happen after you filed that form? I'm wondering if it's worth the effort or if the IRS just files it away somewhere and never follows up.

I don't qualify as independent under any of those categories unfortunately. I'm 20, unmarried, and don't have kids. What's the professional judgment process? Is that different from the dependency override?

Professional judgment is different from dependency override. While dependency override changes your dependency status completely, professional judgment allows financial aid administrators to adjust your financial aid package based on special circumstances. In your case, you'd still need to file as dependent, but the financial aid office could potentially adjust your Expected Family Contribution based on the fact that you're not actually receiving support from your step-father despite what the FAFSA calculations assume. This might not solve your immediate filing problem, but could help with actual aid amounts if you do manage to submit your FAFSA.

This is good advice. I had a scholarship organization work directly with my school when my dad refused to file taxes. They arranged a temporary funding solution while I worked through the dependency override process.

Does the app separate business vs personal miles automatically? That's the part I always mess up. Also, does it integrate with any tax software?

The app lets you swipe right for business trips and left for personal ones after each drive, so it's not fully automatic - you still need to classify them. But it does track all the other details automatically (date, time, route, mileage). And yes, it can export to Excel or CSV formats that work with most tax software. I use TurboTax and it imports the data pretty seamlessly. The peace of mind knowing I have audit-proof records is totally worth the small effort of swiping each day.

This is super helpful perspective! My truck definitely falls into the "gas guzzler with high maintenance" category - it's a 2018 F-150 and I spent almost $4,300 on repairs last year plus all the gas. Sounds like I should really run the numbers on actual expenses based on your experience.

Definitely run the numbers with your specific situation. One other tip - if you go with actual expenses, don't forget to include less obvious costs like depreciation, property taxes on the vehicle, and even insurance. Those can really add up! A vehicle like yours with high repair costs often does better with actual expenses, especially if you're keeping all your receipts. Just remember that with either method, you need to track your business vs. personal miles to determine the business use percentage.