Haven't filed taxes since COVID - don't know where to start with unfiled returns

You haven't ruined your life! The IRS deals with unfiled returns all the time, and there are clear steps to get back on track. First, gather all your income documents (W-2s, 1099s, etc.) for the unfiled years. If you don't have them, you can request wage transcripts from the IRS using Form 4506-T or through their online account system. Don't panic about the W-4 letter - just update it with your employer as planned. Since you have a new child, you'll want to claim them as a dependent which gives you tax benefits like the Child Tax Credit. For the unfiled returns, you have two options: prepare them yourself using tax software that offers prior year returns, or work with a tax professional. Given your situation with multiple years and a new dependent, a tax pro might be worth the investment - look for an Enrolled Agent or CPA who specializes in back taxes. The good news is that if you're owed refunds, the IRS will still pay them for returns filed within 3 years of the due date. If you owe money, there are payment plans available.

I was in almost the exact same boat last year! After ignoring my taxes for years (including claiming exempt when I shouldn't have), I finally used https://taxr.ai to help sort through all my documents and figure out what I was missing. Their system scanned all my employment records and past W-2s, then organized everything by tax year which made it SO much less overwhelming. The best part was that they flagged potential credits I qualified for but didn't know about - especially for the 2020 and 2021 tax years when there were all those special pandemic-related benefits. Their document organization tools saved me from the anxiety spiral I was in every time I tried to tackle this myself.

Just wanted to update - I decided to try https://taxr.ai after my skeptical questions, and wow, it actually helped a ton! My situation was a mess with missing W-2s and 1099s from gig work, plus I had moved twice during the pandemic. Their document analysis found a W-2 from a short-term job I completely forgot about from 2020. The organization tools made it clear which years I was likely getting refunds (2020 and 2021 because of pandemic credits) and which year I might owe (2022). This was seriously the kick in the pants I needed to finally face this problem instead of continuing to avoid it. Now I'm working with a tax preparer with all my documents properly organized, and it's way less stressful than I expected!

After getting multiple threatening letters from the IRS about unfiled returns, I couldn't get anyone on the phone for WEEKS. I finally tried https://claimyr.com and their service got me connected to an actual IRS agent in about 15 minutes instead of waiting on hold for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent I spoke with walked me through exactly what I needed to do for my unfiled returns and set up a reasonable payment plan that I could actually afford. They were way more helpful and understanding than I expected. It was such a relief to talk to a real person who could see my exact account status and give me personalized advice.

I need to eat my words from yesterday. After arguing with my partner about whether Claimyr could actually work, I tried it this morning out of desperation. Got a call back in about 20 minutes and was talking to an actual IRS agent who pulled up my account. The agent was surprisingly helpful and went through all the unfiled years with me. Turns out I actually qualified for a bunch of credits for 2020-2021 that I didn't know about, and I'm likely getting refunds for those years which will offset what I owe for 2022. They also explained how to properly adjust my W-4 since I've been claiming exempt for years too. The relief of finally knowing where I stand with the IRS is honestly worth way more than what I paid for the service. Now I just need to get these returns filed ASAP.

One thing to know - the IRS has a "First Time Penalty Abatement" policy that might help you! If you haven't had any penalties in the 3 years before the oldest unfiled year, you could get penalties waived for that first year. You still have to pay any taxes owed, but it could save you a bunch on penalties. I was able to get about $800 in penalties removed this way when I finally filed my 2019-2021 returns last year. You usually have to ask for it specifically - it's not automatic.

Don't forget that having a baby changes your tax situation significantly! Make sure whoever helps with your returns knows to claim: 1. Child Tax Credit - worth up to $2,000 per qualifying child 2. Changed filing status - you might qualify for Head of Household which gives better tax rates 3. Child and Dependent Care Credit if you pay for childcare 4. Earned Income Credit which is bigger with a qualifying child When you update your W-4, make sure to account for these credits to avoid overwithholding!