Does FreeTaxUSA handle self-employment income too? I've got a mix of W-2 and 1099 income plus the marketplace insurance, so I need something that can handle all of that without costing a fortune.

Yes, FreeTaxUSA handles self-employment income really well. I have both W-2 and 1099 income plus some investments, and it handled everything smoothly. Their interface for Schedule C is actually much better than most paid software I've tried. The only potential downside is that they charge for state filing, but the $14.99 is still way cheaper than most other options like TurboTax or H&R Block which can end up costing $100+ when you have self-employment income.

Thanks for the tip! Did you also have problems with the annual calculation on line 24? Mine keeps showing an error that the annual total doesn't match the sum of the monthly amounts, even though I've checked my math multiple times.

Did you have to provide the documentation with your return or just keep it in case of audit? And did itemizing instead of taking the standard deduction end up costing you more overall? I'm trying to figure out if it's even worth it in my case.

You don't submit the documentation with your return - you just keep it in case of audit. I created a summary sheet that I attached to my return explaining my gambling activity for the year and how I tracked sessions, but the detailed logs and evidence stayed with me. Whether itemizing costs you more depends on your specific situation. In my case, I would have paid tax on $212k of phantom "income" if I had taken the standard deduction, so itemizing was definitely worth it even though I lost some other deductions. You need to compare your potential gambling loss deduction against what you'd get from the standard deduction plus consider any other itemizable expenses you have like mortgage interest, state taxes, and charitable contributions.

I used TurboTax last year for this exact situation. It works fine but you have to make sure you enter everything correctly. Enter all W-2Gs individually where prompted, then when you get to the deductions section, select itemized deductions and enter your gambling losses on Schedule A. The software will compare standard vs. itemized and recommend the better option. One thing TurboTax doesn't do well is explain the documentation requirements, so make sure you have your gambling log and supporting evidence organized separately.

Did you have to pay any penalties for making the estimated payment after the deadline? I'm in the same boat and worried about that.

I haven't received any penalty notices yet. My accountant explained that the penalties for estimated tax payments are calculated annually when you file your next return, not immediately. Since I have documentation showing I requested the proper application on my original return, we plan to request penalty abatement if any penalties show up on next year's return. The penalty would be pretty small anyway - it's calculated based on the underpayment amount, the period it was underpaid, and a relatively low interest rate. For my amount, we calculated it would be less than $30 even if they did charge it.

That's a pretty cynical take. Having worked in tax preparation for years, I'm confident this is just a processing error. The IRS systems are outdated and understaffed. Never attribute to malice what can be adequately explained by bureaucratic inefficiency.

You're probably right. Just feeling frustrated with the whole tax system right now. I've had so many issues this year with errors and delays. It just feels like the deck is stacked against regular taxpayers sometimes.

That's super helpful! I'll check again tomorrow. Did you get any kind of email notification when it was uploaded or did you just happen to check and see it was there?

I didn't get any email notification, I just happened to check and it was there. I know some of my coworkers did get email notifications though, so it seems inconsistent. Might depend on what email preferences you have set up in the HR system. I'd recommend checking once in the morning and once in the evening rather than constantly refreshing. Their system gets really bogged down this time of year with everyone checking for their W2s.

Yep! This happened to me two years ago. My state withholding was completely wrong. I printed what was available and took it to HR, and they had to issue a corrected W2. Took almost 3 weeks to get the fix. I'd recommend comparing your last December paystub (with the year-to-date totals) to your W2 when it arrives to catch any errors early.

We don't actually have a formal custody agreement filed with the court. Everything has been verbal between us so far. I've been trying to avoid court involvement, but maybe I need to get something official in place?

Without a formal custody agreement, the IRS residency rules definitely apply. This means you, as the custodial parent with the child living with you most of the year, have the right to claim him. I would strongly recommend getting a formal custody agreement in place. This protects both you and your child by clearly defining visitation schedules, decision-making authority, and yes, tax claiming rights. Without documentation, these disputes can become "he said/she said" situations that often escalate unnecessarily. A formal agreement can specifically address who claims the child in which tax years, and can be structured in various ways (alternating years, splitting different tax benefits, etc.) if you choose to share this benefit.

This is accurate. My cousin had this exact situation and the judge split the tax benefits - she got odd years and he got even years, even though the kid lived with her most of the time. Judges have a lot of discretion with this stuff.