That's a good point, I hadn't thought about that! When we switched payroll systems, I don't think I filled out a new W-4 for the second one - they might have just used default withholding which would explain the issue. Do you think it's worth asking my HR department if I can see what withholding settings they had for me on both systems?

Absolutely ask your HR department! They should be able to tell you exactly what withholding instructions they had on file for each system. Default withholding typically assumes you're single with no dependents and only one job, which often results in underwithholding if that's not your situation. I'd recommend getting copies of both W-4s they have on file, then filling out a new one with the correct multiple job calculations. The IRS has a good tax withholding estimator on their website that can help you get it exactly right for your situation.

It's not really that payroll systems are terrible - they're doing exactly what they're designed to do. The problem is they only know about the income they're processing. It's actually on us to tell our employers to withhold extra when we have multiple income sources.

That makes sense, but it still feels like the system is unnecessarily complicated. Like why can't the IRS just figure out how much I should be paying based on what I made last year and tell my employers? Seems like they deliberately make it confusing so people mess up and they collect penalties.

TaxSlayer is ok but I found it confusing for itemized deductions. Kept getting different numbers than I expected and couldn't figure out why.

Thanks for the info! I'll probably try FreeTaxUSA based on all the recommendations here. The dated interface doesn't bother me as much as TurboTax's constant upselling. I appreciate the heads-up about the itemized deduction issues. I don't itemize anymore with the higher standard deduction, so hopefully that won't be a problem for me.

How much did you end up paying for H&R Block compared to TurboTax? And did you find it easier to navigate? My main frustration is just wanting to directly enter my forms without going through their "life changes" questionnaire every time.

I paid about $70 for H&R Block's Deluxe version compared to $120 I was paying for TurboTax. It was definitely easier to navigate - they have a "forms mode" that lets you go directly to specific forms without going through all the interview questions first. You can still use the interview mode if you want guidance, but it's completely optional. The interface feels less cluttered too, and I didn't get constant popups trying to upgrade me to more expensive versions.

Did you have to do anything special with FreeTaxUSA for options trades specifically? I've heard they're treated differently than regular stock transactions for tax purposes and want to make sure I'm doing it right.

For options in FreeTaxUSA, you just need to make sure your import file correctly identifies them as options contracts with the right expiration dates and strike prices. The software handles the different tax treatment automatically. One thing to watch for is that some brokers (especially Robinhood back in 2020) sometimes didn't properly classify certain spreads or multi-leg option strategies in their export files. If you did any complex options strategies, you might need to double-check those specific entries, but for simple buys and sells it works perfectly without any special steps.

This is the way. I'm a bookkeeper (not tax professional) and NO reasonable preparer should be charging per transaction when software can import these in bulk. Either hourly or a reasonable flat fee is standard practice for high-volume traders.

Thanks for mentioning this, but my 1099-C is definitely for an old credit card debt, not a home mortgage or farm debt. It was from a major bank that I definitely had an account with back then, so I think it's legitimate. The weird thing is why they waited so many years to cancel it and send the 1099-C. Is there a time limit on when they can issue these forms? The debt was from around 2012, but they just cancelled it in 2023.

There's actually no time limit on when creditors can issue a 1099-C after cancelling a debt. They're required to issue it for the tax year in which they actually cancel the debt, regardless of how old the original debt was. In your case, even though the debt originated in 2012, if the creditor officially cancelled it in 2023, then that's when the taxable event occurred. This is fairly common with old debts that have been sitting in collections for years. The good news is that insolvency is still an option regardless of how old the original debt was. Focus on your financial situation at the time of cancellation (2023) when determining if you qualify for the insolvency exclusion.

That's a great point. Most people filing basic returns won't have these tax attributes, but it's an important consideration if you have a more complex tax situation. Also worth noting that if you're using free tax filing software, some of them don't support Form 982. You might need to upgrade to a paid version to properly handle the insolvency exclusion.

I tried reading the instructions but that's actually what confused me more! They use so many technical terms that reference other technical terms. I felt like I was going in circles. Do you have any suggestions for making sense of all the cross-references in the instructions?

I totally get that feeling! The cross-references can make you feel like you're chasing your tail through an endless maze of tax jargon. What helped me was starting with the glossary section in Publication 17 (the main IRS tax guide) to understand the basic terminology first before diving into specific form instructions. Another approach that helped me was focusing only on the sections relevant to my specific situation and ignoring everything else. For distribution codes, the 1099-R instructions have a table that explains each code - print just that page and highlight only your specific code to avoid getting overwhelmed by all the other possibilities.

This is actually good advice. I was confused about a distribution code on my 1099-R last year and the plan administrator explained everything clearly. They even emailed me a breakdown of the calculation that I could reference when filing.