Anyone know if these carryover losses expire? I've been carrying some forward for a few years now and wondering if there's a time limit before I lose them.

I went through this exact same situation last year with my crypto losses from 2022. The confusion is totally understandable because it does feel like you're claiming the same deduction twice. Here's what I learned after consulting with a tax professional: You should enter the same capital loss carryover amounts on both your federal and state returns. This isn't double-dipping because you're filing two separate tax returns to two different taxing authorities (federal government and state government). California (which I saw you mentioned in the comments) does conform to federal capital loss treatment, so your carryover amounts should be the same on both returns. The key thing to remember is that your federal return calculates your federal tax liability, and your state return calculates your state tax liability - they're independent calculations that both happen to use the same underlying capital loss carryover. TurboTax should handle this correctly once you input the information. The software knows the state-specific rules and will apply them appropriately. Better to use the legitimate deduction you're entitled to than leave money on the table!

14 Be careful with mixing W-2 and 1099 work! I messed up last year and ended up owing WAY more than I expected. Make sure to use the Self-Employment Tax Calculator on the IRS website to estimate what you'll owe.

As a college student who just started mixing W-2 and gig work myself, I can't stress enough how important it is to track everything from day one! I made the mistake of not keeping receipts for my first month of delivery work and it was a nightmare trying to reconstruct my expenses. One thing that really helped me was opening a separate checking account just for my Doordash earnings. I deposit everything there and then transfer my estimated tax portion (about 30%) to a savings account immediately. This way I'm never tempted to spend my tax money and I always know exactly how much I've earned from gig work versus my regular job. Also, don't forget that as a student, you might still qualify for education credits even with the additional 1099 income - just make sure your total income doesn't push you out of eligibility ranges for things like the American Opportunity Tax Credit.

Any recommendations for a good mileage tracking app for Schedule C? I'm constantly forgetting to log my house painting jobs and then trying to reconstruct the miles later which is a nightmare.

This thread has been really helpful! I'm a freelance graphic designer who works with clients both remotely and on-site. I do all my invoicing, client communications, and project planning from my home office (though it's also my bedroom, so no exclusive use deduction). Based on what I've learned here about Revenue Ruling 99-7, it sounds like my home would qualify as my principal place of business for mileage purposes since that's where I conduct all my administrative activities. This means trips from home to client meetings would be deductible business miles on my Schedule C. I've been conservative and only deducting miles between different client locations, but it sounds like I may have been missing out on legitimate deductions. Going to look into that taxr.ai tool mentioned earlier to get a proper analysis of my specific situation. Thanks everyone for clarifying the distinction between home office deduction requirements and principal place of business for mileage!

One thing nobody mentioned - check if any of the shares were ever sold over the years or if all dividends were reinvested. Sometimes with these old custodial accounts, dividends get automatically reinvested which affects your basis. Also if the company was acquired or had spinoffs during that time period you'll need to account for that too.

I dealt with a very similar situation a few years back with inherited stock from my grandfather's employee options at IBM in the 1980s. One resource that helped me tremendously was the IRS Publication 550 (Investment Income and Expenses), which has specific guidance on basis calculations for gifted securities. The key thing to remember is that you need to establish your father's "adjusted basis" at the time of the gift, not just what he originally paid. This includes the exercise price PLUS any compensation income he reported on his W-2 when he exercised the options. If you're still missing records, try contacting the plan administrator (usually the company's HR department or their third-party benefits provider). Even decades later, they sometimes maintain records of employee stock option exercises, especially for larger companies. They might be able to provide a statement showing the exercise date, number of shares, exercise price, and fair market value at exercise. Also keep detailed documentation of your efforts to reconstruct the basis - the IRS generally accepts reasonable estimates when you can demonstrate good faith effort to determine the correct amount.

This is a really common situation that catches a lot of people off guard! The main culprit is definitely the Earned Income Tax Credit (EITC) like others mentioned. At $27k with 4 dependents, you were probably getting the maximum EITC of around $6,000-7,000, but at $54k you're likely getting little to none of it. Here's what probably happened: Last year your total tax liability was probably very low (maybe $2,000-3,000) but you got huge refundable credits that gave you that $14,750 refund. This year, even though you're paying more in actual taxes, those big credits are mostly gone. The silver lining is that you're definitely better off financially overall - you're keeping way more money throughout the year in your paychecks. That $14k refund was essentially the government giving you your own money back that they over-collected, plus credits for being lower income. For next year, I'd suggest using the IRS withholding calculator and maybe having a bit extra withheld if you want a bigger refund. Also look into maximizing any retirement contributions (401k, IRA) since those can lower your taxable income and potentially help you qualify for more credits.

This thread has been incredibly helpful! I'm in a similar boat - made $31k last year and getting around $8,500 back, but this year I'm projected to make about $48k and worried about what that means for my refund. Reading through all these responses, it sounds like the EITC phase-out is the big killer here. @Hattie Carson's point about using 401k contributions strategically is really smart - I hadn't thought about working backwards from the optimal AGI. One question I have is about timing. If I realize mid-year that my income is going to push me out of credit ranges, is it better to max out retirement contributions early in the year, or can I adjust anytime? Also, does anyone know if HSA contributions work the same way as 401k for lowering AGI? Thanks everyone for sharing your experiences and solutions. This is way more useful than trying to decode IRS publications on my own!