Thanks for mentioning this! I've definitely filed and paid on time for the last several years. How do I request this abatement? Is it something I ask for when setting up the payment plan, or is it a separate process?

You can request it when you call to set up your payment plan. Just specifically mention that you'd like to request a "First Time Penalty Abatement" based on your history of compliance. The agent should be able to check your eligibility on the spot. If they approve it, they'll remove the failure-to-pay penalties, though interest will still apply to your balance. If you set up your payment plan online, you'll need to call separately to request the abatement. Make sure to do this sooner rather than later - it's easier to get penalties removed before you've paid them than to get a refund afterward.

This is super important! My brother had to pay penalties two years in a row because he didn't adjust his withholding after the first time he owed a lot. The second time, the IRS was way less forgiving about waiving penalties.

Omg I didn't even think of this! I usually toss anything that looks like junk mail right away. I'm gonna go through my mail pile tonight to double check. Do you remember what the envelope looked like exactly? Was it white or brown or what?

It's usually a plain white envelope with a very official looking "Department of the Treasury" return address from Kansas City or Philadelphia. Nothing flashy at all - it's actually designed to not look like it contains something valuable for security reasons. The tax refund debit cards are even worse - they come in white envelopes with "Money Network Cardholder Services" as the sender, which looks exactly like credit card spam. Check your mail pile carefully and maybe even look through your recycling if you can!

This happened to me 2 years ago. Filed with my old address by mistake and my check got sent back to the IRS. Took another 2 months to get it sorted out! Always double-check your address on the tax forms.

This is an excellent point. I previously worked for a farming cooperative and sometimes payments were categorized as "rent" when they were actually for other services. One family had their grandson handle paperwork and communication with us, and he received a 1099 for his administrative services while the actual landowners got a separate payment.

That's actually a really good idea. I don't know why I didn't think of that. I have his phone number from previous communications about the checks. I'll give him a call tomorrow to clarify the situation. I guess I was overthinking this whole thing.

I get a different error every year with TurboTax 🙄 Last year I switched to FreeTaxUSA and haven't looked back. Way cheaper and actually explains errors better.

I actually tried that first! We used Workday, but my login stopped working shortly after I left the company. I called about getting it reactivated but that just led me back to the same HR department that never answers. Frustrating because I know the W-2 is probably sitting right there in the system.

That's unfortunately pretty common - companies often disable access but don't communicate how former employees should get their tax documents. One thing you could try is reaching out to your former manager or even colleagues still at the company. Sometimes they can put internal pressure on HR that gets better results than calling from the outside. If that doesn't work, a former coworker might be able to tell you who specifically in HR handles tax documents, so you could email them directly instead of calling the general HR line. Large companies often have dedicated tax specialists who are separate from the regular HR team.

This actually worked for me last year! I filed a complaint with my state labor board and they contacted my former employer. Got my W-2 within a week after months of trying on my own.