Haven't filed 2022 taxes yet - just got money to pay. Can I still e-file after the October extension deadline?

If I'm in a similar situation but I actually might be due a refund (had too much withheld), do the same penalties apply? And would I still be able to get my refund for 2022 if I file now?

If you're due a refund, there's actually no penalty for filing late! The IRS doesn't penalize you for filing late when they owe YOU money. However, you only have 3 years from the original due date to claim a refund, so for 2022 taxes, you have until April 15, 2026 to file and still receive your refund. After that 3-year window closes, you lose the right to your refund money completely. So while there's no immediate penalty, there is a deadline to be aware of. I'd still recommend filing sooner rather than later to get your money back.

Does it work with complicated situations? I'm self-employed with multiple income streams and I'm 2 years behind on filing. Would it help with finding all the deductions I might be eligible for?

I'm skeptical about giving my tax docs to some random AI tool. How secure is it? And does it actually connect with the IRS or just give generic advice?

For self-employed situations, it's actually super helpful because it categorizes expenses properly and explains which ones might trigger audit flags. It found several home office and vehicle deductions I didn't know I qualified for even with my weird income setup. Regarding security, they use bank-level encryption and don't store your documents after analysis. It doesn't file directly with the IRS - it's more like having an expert review everything before you submit, pointing out opportunities and mistakes. You still use your regular tax software to actually file.

How does that even work? The IRS phone system is completely broken - I tried calling 8 times last month and never got through. Is this some kind of scam or do they have some special connection?

Yeah right. Nobody can get through to the IRS these days. I literally spent 14 hours on hold last week and got disconnected. There's no way this actually works.

It uses a combination of tracking the IRS phone system patterns and automated call technology. Basically it keeps calling and navigating the phone tree until it gets a spot in line, then alerts you when it's about to connect with an agent. So you don't waste hours on hold. No special connection - they just have technology that makes thousands of calls and knows exactly when to get you in the queue. It's completely legit - you talk directly to regular IRS agents who have no idea you used a service to connect.

Wait, really? That would be amazing. Do I have to specifically ask for this program by name when I contact them? And would I qualify even though I had the extension and still missed it?

Yes, you should specifically ask for "First Time Penalty Abatement" when you contact them after filing. Don't rely on them to offer it - many IRS agents won't mention it unless you ask. You would likely still qualify despite missing your extension deadline. The main requirement is having a clean compliance history for the three prior tax years (meaning you filed and paid on time, or had valid extensions and paid by those deadlines). The IRS sees this as a one-time courtesy for otherwise compliant taxpayers.

I'm so sorry about your mom. I was in a similar situation with my father's passing. The IRS does have something called "reasonable cause" for penalty relief. You'll need to attach a letter explaining the circumstances and showing how the death and estate duties prevented you from filing on time. Include any documentation you can (death certificate, executor appointment papers). In my experience, they were actually pretty understanding.