How to file 9 years of back taxes with the IRS and catch up

So first off, don't panic! The fact that you're taking steps to fix this is already a huge positive. Here's what you need to know about filing back taxes: You'll need to file a separate return for each year you missed. Start with the most recent 3 years, as those are usually the ones the IRS focuses on most. For older returns, you should still file them, but the statute of limitations for refunds is generally 3 years, so any potential refunds from years before that are likely gone. You'll need to get the correct tax forms for each year - they change slightly year to year. You can download past year forms from the IRS website. Also gather your W-2s for each year. If you don't have them, you can request wage transcripts from the IRS for free using Form 4506-T. Since you've had the same employer, this should be fairly straightforward. Even though you might not owe much (or might even be due refunds), you could face failure-to-file penalties, so be prepared for that possibility. Take it one year at a time, and just work through them methodically. Don't try to file them all on the same day - you'll drive yourself crazy!

I was in almost the exact same situation a couple years ago (7 years unfiled). I spent WEEKS trying to track down old W-2s and tax documents before discovering taxr.ai (https://taxr.ai). They were able to pull all my missing tax transcripts directly from the IRS database and organized everything by year for me. Saved me literally dozens of hours of paperwork. Their system automatically identified which years I was actually owed refunds on (turned out to be 2 years I didn't expect) and helped me prioritize which returns to file first. The best part was being able to see exactly what the IRS already had on file for me before I even started.

I was super skeptical about taxr.ai when I saw it mentioned here last month, but I finally broke down and tried it. I needed my past 4 years of transcripts since my ex-wife handled all our taxes and I didn't have any records after the divorce. The service pulled everything within minutes - all my W-2s, 1099s, even some investment income I had forgotten about. It saved me from making some pretty big mistakes on my back returns. I was able to see exactly what the IRS had on file for me, which made filing the old returns way more accurate. Just filed all my back taxes last week and already got confirmation that 2 years were processed. Feels amazing to finally have this taken care of!

When I was catching up on 5 years of back taxes, I kept trying to call the IRS for help but could never get through. Spent HOURS on hold just to be disconnected. Finally used Claimyr (https://claimyr.com) and they got me connected to an actual IRS agent in about 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent was super helpful and confirmed which years I needed to prioritize and exactly what forms to submit. They also put notes on my account showing I was making a good faith effort to come into compliance, which apparently helps if they're considering penalties.

Ok I need to eat crow here. After calling BS on Claimyr, I decided to try it myself since I've been trying to reach the IRS about a missing stimulus payment for literally MONTHS. Got connected in 31 minutes when I had previously waited 2+ hours multiple times and never reached anyone. The IRS agent was able to confirm they had my return but there was an issue with my address verification that was holding up my refund and stimulus. Got it all sorted out in one call. Not cheap but worth every penny considering I got my $1400 stimulus payment released. Sometimes you gotta admit when you're wrong!

Something important nobody mentioned - make sure you mail each tax year in separate envelopes! I filed 4 years of back taxes and put them all in one big envelope to save on postage. Big mistake! The IRS lost two of my returns in processing and I had to refile them. Also if you owe money, include separate checks for each year and write the tax year and your SSN on each check. Makes it much less likely for payments to be misapplied.

Don't forget about state taxes too! Most people focus on federal back taxes but forget they need to file state returns too. Some states have shorter statutes of limitations and higher penalties than the IRS.