Need help with IRS extensions for multiple years (2016, 2023, 2024) and owed taxes - overwhelmed!

Wow, that's a lot to handle! I've dealt with tax extensions before, but not for multiple years like that. Have you tried calling the IRS directly? They might be able to guide you through the process.

I found a way to actually get someone on the phone at the IRS. I used this site's (claimyr.com) calling tool that dials the phone menu, stays on hold, waits for a live agent to pick up, then sends the call to my phone. It does cost $20, but it works. Here's a video about it: https://youtu.be/bA59vpIwDRU

Listen up, OP. Here's what you need to do: 1. File Form 4868 for each year you need an extension (2023 and 2024). This gives you an automatic 6-month extension to file. 2. For 2016, you're past the deadline for extensions. You'll need to file ASAP and may face penalties. 3. Remember, extensions give you more time to file, NOT more time to pay. You should still pay what you estimate you owe to avoid penalties and interest. 4. For the money you owe, look into an installment agreement (Form 9465) if you can't pay in full. 5. Consider getting professional help. A tax pro can navigate this complex situation and potentially save you money in the long run. Good luck, and don't put this off any longer!

bruh how do you need an extension for 2024 taxes? Time traveler much? 🤣

I feel your pain, OP. The IRS is a labyrinth of bureaucracy and confusing forms. Have you considered hiring a tax attorney? They can be expensive, but might be worth it for your situation.

Whatever you do, DON'T ignore this. I made that mistake and ended up owing way more in penalties and interest. Face it head-on, even if it's scary.

Am I the only one who thinks its ridiculous that we have to jump through all these hoops just to pay our taxes? The system is broken, man. 🤡