Anyone else feel like tax software is designed to make us think we're getting less so we'll upgrade to their paid versions? Every time I use the free version it shows a tiny refund, then magically finds more money when I upgrade. Seems suspicious.

Your situation is totally normal! I went through the exact same thing two years ago and panicked thinking I'd made a mistake. Turns out my withholding just got more accurate when I started a new job. Here's what probably happened: when you started your new jobs, HR likely had you fill out a W-4 form. The newer W-4 calculations are much more precise than the old system, so instead of over-withholding (which gives you a big refund), they're taking out closer to what you actually owe. Quick math check: if you made $6k more but only got $785 less in refund ($850 - $65), you probably had about $5,215 more in your actual paychecks throughout the year. That's money you got to use all year instead of lending it to the government interest-free! Before paying someone to look at your taxes, just double-check that you entered everything correctly in TurboTax - both W-2s, any 1099s, and that you claimed the standard deduction. If everything looks right, you're golden. Your withholding is just working the way it's supposed to now.

Does anyone know if this applies to rideshare/public transportation too? I don't have a car so I'm spending like $20-30 per day on Uber or train tickets to get to different event venues. Same situation as OP where I'm a W-2 employee but work at different locations all over the city.

I'm in a very similar situation working for multiple event companies! One thing that's helped me is keeping extremely detailed records of all my work locations and mileage. I use a simple spreadsheet with columns for date, client/event, venue address, miles from home, and whether it's a one-time or recurring location. Even though we can't deduct these costs directly as W-2 employees right now, having this documentation has been invaluable when discussing reimbursement with employers. I've found that smaller event companies are often more willing to work with you on travel costs when you can show them the actual financial impact. Also, don't forget to factor in your time spent traveling when evaluating job offers. I started declining gigs that were more than 60 miles away unless they paid significantly more to offset the travel costs and time. It's helped me be more strategic about which events I accept. The tax landscape might change after 2025 when the current restrictions on employee deductions expire, so definitely keep those records for the future too.

This might be a stupid question but I'm confused about how this affects penalties. If I'm someone who normally just gets a W-2 and doesn't need to make estimated payments, can I still use this trick to overpay and get a refund? Or will I get hit with some kind of penalty for paying taxes late even though I'm overpaying?

One thing to keep in mind is the timing of your refund if you're planning this for credit card rewards. The IRS typically processes refunds within 21 days of receiving your return, but this can be longer during busy filing season (especially February-April). If you're counting on getting your overpayment back quickly to pay off your credit card before interest kicks in, make sure you have a backup plan in case the refund takes longer than expected. I learned this the hard way when my refund was delayed by 6 weeks due to additional review, and I ended up paying interest on my credit card balance. Also, remember that if you overpay by more than $1, the IRS will send you a paper check rather than direct deposit unless you specifically request direct deposit on your return. The paper check adds another week or two to the process.

Don't forget to check if your state requires filing too! I had zero federal income in 2020 but my state still required a return because I had received unemployment earlier in the year. Each state has different rules.

@Danielle Mays - You're getting great advice here! Just to add a few practical tips: Since you mentioned health issues in 2021, make sure to check if you had any health insurance marketplace coverage or received any advance premium tax credits. Even with zero income, you might need to reconcile those on Form 8962 if applicable. Also, gather any 1099s you might have received (even for small amounts like bank interest) since those would need to be reported. The IRS already has copies of these forms, so it's better to include them even if the amounts are minimal. One more thing - if you were claimed as a dependent on someone else's return in 2021 (like a parent or spouse), that would affect your filing requirements and stimulus eligibility. Make sure to clarify your dependency status for that year before filing. The good news is that with zero employment income, your return should be relatively straightforward once you determine if you actually need to file or if you're just filing to claim credits/refunds!

Does anyone know if having unpaid court fees affects filing taxes? I still owe about $3,500 in restitution and I'm worried they'll take my refund if I file.

Hey, I'm really glad you're taking this seriously and getting your life back on track! Filing taxes can definitely feel overwhelming at first, but you've got this. A few things to add to what others have said: 1. **You're required to file** - Since you made $27,000, you're well above the filing threshold, so yes, you do need to file by April 15th. 2. **No special forms needed** - Your parole status doesn't require any special tax forms or disclosures to the IRS. Just file like anyone else with your income level. 3. **Watch your withholdings** - Check your paystubs to see if enough tax was withheld. Sometimes people coming out of incarceration don't realize they need to adjust their W-4 form with their employer. 4. **Free filing options** - If your income is under $73,000 (which it is), you can use IRS Free File. Go to irs.gov and look for "Free File" - it'll connect you with free software that walks you through everything. 5. **Keep your PO informed** - It sounds like you're already doing this, but letting your parole officer know you're handling your tax obligations shows you're being responsible. The fact that you're asking these questions and trying to do everything right shows you're on the right path. Don't let the process intimidate you - thousands of people file their first tax return every year and figure it out just fine.