Do you know if FreeTaxUSA can import previous year's TurboTax returns? Or would I need to enter everything manually the first time I switch?

You'll need to enter your information manually the first year you switch. FreeTaxUSA can't directly import TurboTax returns, which is honestly the biggest downside of switching. However, you can reference your previous TurboTax PDF while entering info, and after that first year, FreeTaxUSA will import your previous FreeTaxUSA return data. The manual entry took me maybe an extra 20-30 minutes the first year, but I've saved much more than that in both money and time (avoiding upsells) every year since.

I used Cash App Taxes last year after using TurboTax for years. It's legitimately free and worked fine for my relatively simple return (W-2, some investment income, student loan interest deduction). The interface is decent but not as hand-holdy as TurboTax. The only limitation I found is that it doesn't support multiple state returns, foreign income, or some more complex situations like trusts. But for most people with straightforward taxes, it's a solid free option.

Do you know if you can still access those systems if you no longer work for the company? I left my job last August but never set up the payroll portal while I worked there.

You can usually still access them even if you no longer work there. The accounts stay active for tax purposes. If you never set up the portal, you might need to register for the first time - you'll typically need your SSN, DOB, and sometimes a company code (you can call the payroll company's support line to get this). If it's ADP specifically, go to their website and look for "First Time User" registration. Similar process with other payroll services. They'll verify your identity and then you should be able to access all your tax documents!

I tried that with H&R Block's software but it only worked for my current employer. Couldn't pull any data from my previous jobs. Might depend on which payroll system the company uses.

Thanks for sharing your experience. Do you remember roughly how much the interest rate was? And did you end up just paying what they asked for in the letter or did you have to file an amended return anyway?

The interest was running around 5-6% annually, but it was the failure-to-pay penalty that really added up - that's 0.5% per month up to 25% of the unpaid tax. The notice gave me the option to just pay what they calculated or file an amendment if I disagreed. I just paid their amount since it was accurate. The CP2000 notice actually makes it pretty simple - they show what they found, calculate the difference, and give you payment options. You only need to file an amendment if you disagree with their calculations or if the missing income affects other parts of your return like credits or deductions.

Yes! This is what I did when I was missing a W-2. Just go to the IRS website and request a "Wage and Income Transcript" for the tax year you're concerned about. It shows everything reported to the IRS under your SSN including all W-2s, 1099s, etc. Super helpful for catching these issues before they become problems.

I think I'll make around $18,000 this year if I keep working the same hours, so I guess I will have to file? And yes I'm pretty sure my grandparents claim me as a dependent since I live with them and they pay for most of my stuff. Does that change things?

Yes, at $18,000 you'll definitely need to file a tax return. Being claimed as a dependent does change things a bit. You won't be able to claim your own personal exemption, and there are some credits you might not qualify for. Make sure to check the box on your tax return that says someone else can claim you as a dependent. This is important because if you don't check it but your grandparents claim you, it will create problems for both returns. Also, as a dependent with income, you'll need to file your own return - your grandparents can't include your income on their return.

This!!! Also, set a calendar reminder for mid-February to check if you've received your W-2. If you haven't gotten it by February 15th, you should contact your employer. They're legally required to send it by January 31st.

Would keeping a log of hours worked (which would be basically zero) help document this? I have a similar situation but with a small rental property in my S-Corp that basically runs itself through a property management company. I literally spend maybe 2-3 hours per YEAR on it.

Yes, a log of hours would be extremely helpful documentation. For your situation with just 2-3 hours annually, that's exactly the type of minimal involvement that supports a no/low salary position. I'd recommend documenting not just the hours but specifically what you do during those hours. Show that you're only making high-level oversight decisions while the property management company handles all the actual work. Include copies of your property management agreement in your corporate records to further substantiate your minimal involvement.

The accumulated earnings tax doesn't apply to S-Corps, only C-Corps. S-Corps are pass-through entities where income is taxed to shareholders regardless of whether it's distributed. The penalty you're probably thinking of is for personal holding companies, which is different.