I missed the IRS deadline to file for an extension - is there any way to still request one?

But what if they had a really good reason for missing the deadline? Like a family emergency or something? Doesn't the IRS have some kind of forgiveness program?

The IRS may provide penalty relief if you had a legitimate reason for missing the deadline, such as a serious illness, natural disaster, or certain other circumstances beyond your control. This is called "reasonable cause." You'd need to attach a statement to your return explaining the situation when you file. However, simply forgetting or being busy with work/life changes typically doesn't qualify as reasonable cause in the IRS's view. Still, it's always worth explaining your circumstances when you file.

Does this actually work for calculating failure to file penalties? I'm in a similar situation and wondering if it can help me figure out exactly what I'll owe.

I'm skeptical about these tax tools. How accurate was it? Did you end up having to pay exactly what it predicted or was it way off?

Yes, it actually does calculate failure to file penalties based on your specific situation including how much you owe (if anything) and how late you are. It gives you a pretty clear breakdown of what to expect. The penalty predictions were surprisingly accurate in my case. It estimated I'd owe about $215 in penalties and interest, and the actual bill I got from the IRS was $232. The small difference was just because of a few extra days of interest accumulation by the time everything processed.

How does this actually work though? They have some special connection to the IRS or something? Seems weird that they could get through faster than regular people.

Sorry but this sounds like BS. There's no way to "skip the line" with the IRS. Everyone has to wait on hold. This is probably just a scam to get your money and personal info.

They don't have any special connection to the IRS or skip any lines. What they do is use an automated system that waits on hold for you so you don't have to sit there with your phone for hours. When an IRS agent finally picks up, their system calls you and connects you directly with that agent. It's definitely not a scam. I was skeptical too initially, but it's just a time-saving service. They don't ask for any tax info or personal details - they just need your phone number to call you back when an agent is on the line. You're still the one talking directly to the IRS, they just handle the hold time for you.

Thanks for the tip about First Time Penalty Abatement! I didn't know about that. I've always filed on time before this year so maybe that could help me. Do I need to request that when I file or is it something I do afterward?

You should request First Time Penalty Abatement after you file your return and after the IRS sends you a notice assessing the penalties. You can call the IRS directly (the phone number will be on your notice) and request it, or you can write a letter requesting the abatement. Make sure to mention specifically that you're requesting "First Time Penalty Abatement" and that you have a history of compliance for the past three years. It's a relatively straightforward process for most people who qualify, but you do need to proactively ask for it - they won't automatically apply it.

You can absolutely still use tax software to file late! I filed 2 months late last year using TurboTax with no issues. Most tax software can e-file returns for the current tax year until around November, after which you might need to paper file.

This is really solid advice, @Zachary Hughes! I'm in a similar boat as Diego and had no idea about the First Time Penalty Abatement option. Quick question - do you know roughly how long it takes for the IRS to process that request once you submit it? I'm trying to figure out if it's worth waiting for their penalty notice or if I should just plan to pay the penalties upfront when I file.

@Brooklyn Foley From my experience, the IRS typically takes 4-6 weeks to process a First Time Penalty Abatement request once you call or send in the written request. I d'definitely recommend just filing your return now and paying what you can, then waiting for the penalty notice to arrive usually (2-4 weeks after filing .)Don t'pay the penalties upfront when you file - let the IRS assess them first, then request the abatement. If they approve it, you ll'only owe the interest portion, which is much smaller. If they deny it which (is rare if you truly qualify ,)you can always pay the penalties then. This approach saves you from potentially overpaying and having to wait for a refund.

@CosmicCommander This is really helpful advice! I'm also dealing with a late filing situation and wondering - when you mention paying "as much as you can afford right now," do you mean I should estimate what I owe and send a payment with my return, or should I wait until I actually file to see the exact amount? I'm worried about overpaying or underpaying if I try to estimate.

@Logan Greenberg You should definitely wait until you actually prepare your return to know the exact amount you owe - don't try to estimate and send a payment beforehand. When you file your return (whether through tax software or paper), you'll see exactly how much you owe in taxes. At that point, pay whatever amount you can afford along with your return submission. If you can't pay the full amount, don't let that stop you from filing! The failure-to-file penalty is much worse than the failure-to-pay penalty. You can always set up a payment plan with the IRS afterward for any remaining balance. The key is getting that return filed ASAP to stop the failure-to-file penalty from growing.