Thanks for this! I didn't track my miles super carefully since I only drove for those couple days. Is there any way to reconstruct this after the fact or am I just out of luck?

You can try to reconstruct your mileage based on records you might have. Lyft should have records of the actual rides and miles driven with passengers, but that doesn't include the miles driven between rides or positioning yourself. If you have a general idea of the areas you worked and approximately how much "dead" mileage you had between rides, you can make a reasonable estimate. Some tax pros recommend using a 1.2x to 1.3x multiplier on your actual ride miles to account for the between-ride miles, though this varies based on your market.

Is there a way to calculate approximately how much I should set aside? I just started doing Instacart as a side gig.

Does CashApp Taxes handle cryptocurrency transactions? I did a bit of trading last year along with my regular job and some freelance work, so I need something that can deal with all of that.

CashApp Taxes has basic support for cryptocurrency transactions, but it's somewhat limited. You'll need to enter your transactions manually or import a summary from your exchange. For more complex crypto situations with lots of trades, you might want a more specialized solution. For your combination of W-2, freelance, and crypto income, TaxAct might actually be the better choice. Their crypto reporting tools are more robust and they integrate with several popular crypto exchanges for easier importing. They've really improved their crypto support over the last couple years as it's become more common.

Have you ever had your return audited using OLT? I'm always worried the cheap options might miss something or not be as thorough.

Just checked out OLT - that price is insane! But their website looks super dated. Does it handle Schedule C for self-employed people well? And how's the user experience? I don't mind basic interface if it works properly.

That's actually really reassuring. I've been losing sleep over this! So you think filing amended returns is the way to go? About how much should I expect to pay in penalties if I come forward voluntarily?

Filing amended returns is definitely the right approach. For voluntary corrections, you'll likely just pay the additional tax you would have owed originally, plus interest on that amount from the original due date. The interest rates change quarterly but have been around 5-7% recently. If the IRS assesses penalties, the most common one would be an accuracy-related penalty of 20% of the unpaid tax amount. However, these are often waived or reduced when you voluntarily come forward to fix honest mistakes, especially for relatively small amounts. You can also include a letter explaining your misunderstanding of the rules when you file the amended returns, which can help your case further.

Do you think the 100% business use claim could push this into fraud territory though? That seems like a pretty obvious misrepresentation, especially for a college student who would clearly need the car for personal stuff too.

This is really helpful context! My settlement was definitely for workplace harassment with emotional distress, no physical injury component. Based on what everyone's saying, it sounds like I'm eligible for that above-the-line attorney fee deduction, which is a huge relief. Do you know if I need to include any specific documentation with my tax return to prove the nature of the settlement? Or is just noting it on Schedule 1 enough?

You don't need to submit your actual settlement agreement with your tax return, but you should include a statement that explains the nature of the settlement and why you're reporting it the way you are. Something simple like "Line 8z includes $67,500 received as settlement for emotional distress from workplace harassment. Line 24h includes $28,200 in related attorney fees and legal costs." Keep your settlement agreement, court documents, and records of attorney payments with your tax records. If you're ever audited, you'll need these to substantiate both the nature of the settlement and the attorney fee deduction. The IRS typically has 3 years to audit, so keep those records for at least that long.

Texas doesn't have state income tax, so OP doesn't need to worry about that part at least!

This is super helpful, thank you! How long did it take them to respond to your abatement request? And did you have to provide any specific evidence beyond just pointing out the timeline?

It took about 6 weeks to get a response, which was actually faster than I expected. I didn't need special evidence beyond clearly outlining the timeline with specific dates. One tip - I made sure to include all the reference numbers from the CP2000 notice at the top of my letter and made it very clear I wasn't disputing the actual adjustment, just the interest. I think that helped it get processed faster since they knew I wasn't challenging the underlying tax assessment. I also kept it to one page and very factual - no emotional language about how unfair it was. Just dates, facts, and the specific tax code.

I tried the Taxpayer Advocate last year for a similar issue but they told me they couldn't help because it wasn't an "economic hardship" situation. Seems like they're really only equipped to help if you're facing immediate financial difficulty, not just regular interest disputes. Worth a shot I guess but they're also super backed up these days.

Good point about the hardship requirement. I think my situation qualified because I was facing a lien at the time. For regular interest issues, probably better to go with the interest abatement request directly to the IRS like others mentioned. The Taxpayer Advocate is really more for when you're truly stuck in the system or facing serious consequences.