Has anyone had success just checking the "Exempt" box in Workday for a paycheck or two? I'm considering this but not sure of consequences...

I completely understand your frustration with the new W-4 form! I went through the exact same thing last year and felt like I needed a degree in tax law just to adjust my withholding. Here's what worked for me: The quickest way to increase your take-home pay temporarily is to use Step 4(b) "Other Deductions." In Workday, this might be labeled as "Additional Deductions" or something similar. You can enter a dollar amount here that reduces your taxable income for withholding purposes. A rough rule of thumb: if you're in the 22% tax bracket and want an extra $200 per paycheck, you'd enter about $4,500-$5,000 in deductions (this assumes biweekly pay). The system will withhold less tax because it thinks you have more deductions coming. Just remember to change it back after a few paychecks! I set a calendar reminder because it's easy to forget. Also keep in mind you're just borrowing from your future tax refund - you'll still owe the same total tax for the year. The Workday interface is definitely confusing compared to the actual IRS form, but once you find that deductions field, it should do what you need.

One thing that might help ease your stress - the IRS is generally more interested in getting you back into compliance than in punishing you. They see situations like yours all the time, especially after the chaos of the past few years. When you're gathering documents, don't forget about things like state tax refunds you might have received (those can be taxable income), unemployment benefits, or any side gig income from apps like Uber, DoorDash, etc. These smaller income sources are easy to forget but can add up. Also, if you moved during those years, make sure you're filing in the correct states. Some states have no income tax, others do, and you might owe taxes in multiple states depending on when you moved and where you worked. The key is just to start. Pick one year (I'd suggest 2020 since it's the oldest) and focus on getting all the documents together for just that year first. Once you see how the process works for one year, the others will feel much more manageable. You've got this!

I went through something very similar a few years back - hadn't filed 2018-2020 due to job changes and personal issues. The anxiety was honestly the worst part! Here's what worked for me: Start by requesting your wage and income transcripts from the IRS website (irs.gov/individuals/get-transcript). This will show you exactly what income the IRS has on record for each year, which helps you identify any missing documents and gives you a baseline to work from. One thing that really helped my peace of mind was calling the IRS Taxpayer Advocate Service (1-877-777-4778). They're specifically there to help people in situations like yours get back on track. They can't do the filing for you, but they can explain your options and help you understand what to expect in terms of penalties. Don't beat yourself up about this - life happens, and you're taking the right steps now. The IRS would much rather have you file late than not at all. Focus on getting organized first, then tackle one year at a time. You'll feel so much better once you start making progress!

I noticed nobody mentioned state taxes. Depending on your state, you might need to add the HSA distribution to your state taxable income too. Some states like California don't recognize HSAs at all, which makes it even more complicated. FreeTaxUSA should handle this automatically, but it's good to be aware.

I went through this exact same situation a couple years ago and want to add something that might help save you some money. Before you finalize everything in FreeTaxUSA, double-check if any portion of your HSA withdrawal might qualify for penalty exceptions under IRS Publication 969. There are several situations where the 20% penalty can be waived - things like disability, unemployment for more than 12 weeks, certain higher education expenses, or first-time home purchase (up to $10,000). Even if the expenses weren't medical, you might still avoid the penalty if you meet one of these other criteria. When you're in the HSA section of FreeTaxUSA, there should be questions about whether you qualify for any penalty exceptions. Don't just assume you'll pay the full 20% penalty without checking these options first. I saved myself about $600 by discovering I qualified for the unemployment exception.

Has anyone had experience with e-filing a deceased taxpayer's return as a Personal Representative? I'm trying to avoid paper filing if possible, but I'm not sure if the major tax software programs properly handle this situation.

I'm currently going through this same situation with my father's estate. One thing I want to emphasize that hasn't been fully covered - keep detailed records of EVERYTHING you do as Personal Representative. The IRS may request documentation later, and having organized files will save you major headaches. Also, consider getting an EIN (Employer Identification Number) for the estate if there are any ongoing income-generating assets or if you expect the estate to remain open for an extended period. This separates estate income from the final 1040 and helps with record-keeping. For the signature issue specifically, I found it helpful to practice writing "John Doe, Personal Representative for [Deceased's Name], Estate" a few times before signing the actual return. The IRS wants clarity about who is signing and in what capacity.

I made this exact mistake my first two years in business and it ended up triggering a letter from the IRS. They have reports from payment processors about how much you processed, so if there's a big discrepancy they'll notice. Better to do it right and avoid the headache!

This is such a helpful thread! I've been making the same mistake with my freelance graphic design business. I use Stripe and have been only reporting the net amounts that hit my bank account. Reading through all these responses, it's clear I need to start reporting the gross amounts on line 1 and then deducting the Stripe fees separately. I'm actually relieved to learn that even though I've been doing it wrong, my net taxable income probably hasn't been too far off since I wasn't claiming the processing fee deductions either. Going to dig up my Stripe annual statements and see if I can figure out the correct numbers for this year's filing. Thanks everyone for sharing your experiences - makes me feel less alone in being confused about this stuff!