23 quick PSA: If you qualify for IRS Free File (income under $73,000), you can use free versions of tax software even for prior years. go to irs.gov/freefile and check which ones offer prior year returns. i did 2 years of back taxes thru them last yr for $0.

$695 for three years seems reasonable but not necessarily the best deal. I was in a similar situation and ended up going with a local CPA who charged $450 for three years of back taxes. The advantage was that they also helped me set up a payment plan with the IRS since I owed money, and they were available for questions during the process. If you're comfortable with technology and your situation is straightforward like you described, definitely consider the DIY route. I used TurboTax's prior year versions for my spouse's back taxes (simpler situation) and paid about $60 per year vs the $230+ per year Liberty quoted you. One thing to keep in mind - if you end up owing money, you'll want to file ASAP regardless of which route you choose. The failure-to-file penalty is much higher than the failure-to-pay penalty, so getting those returns submitted should be your priority even if you can't pay the full amount right away.

The 1099-Q situation can be super confusing. One thing to keep in mind is that the IRS gets a copy of every 1099-Q that's issued. They do have a matching program, but they also understand that most 529 distributions are tax-free. In my experience, as long as you have sufficient qualified education expenses, you won't trigger any issues. I've been handling my kids' college expenses with 529 plans for years, sometimes with the student as recipient and sometimes with me as recipient. I report my 1099-Qs on my return, and my kids don't file returns if they're below the filing threshold, even with their 1099-Qs. Never had any issues or notices from the IRS about this. Just make sure you're not claiming education credits for the same expenses that were paid with 529 funds.

This is a really helpful thread! I'm dealing with a similar situation but with an added wrinkle - my son changed schools mid-year, so we have 1098-T forms from two different universities. We also had some 529 distributions go directly to the first school, some reimbursements to me, and then direct payments to the second school. From reading all the responses here, it sounds like as long as the total qualified education expenses exceed the total 529 distributions, we should be fine tax-wise. But I'm wondering about the education credit calculation when you have multiple schools involved. Do I need to calculate the credit separately for each school, or can I combine all the qualified expenses and then subtract the total 529 distributions? Also, has anyone dealt with the situation where a 529 distribution was made but then the student withdrew from classes and we had to return some tuition to the school? The 1099-Q still shows the full distribution amount, but technically not all of it was used for qualified expenses in the end.

Quick question - if I'm getting a refund (I'm like 99% sure based on my rough calculations), do I still need to file an extension? Or is the extension only necessary if you're going to owe money?

Just wanted to add one more thing that might help with your extension stress - you can actually amend your extension payment if you realize you underpaid! I found this out the hard way last year when I filed my 4868 and paid what I thought I owed, but then realized I had forgotten about some 1099 income a week later. I was panicking thinking I'd get hit with penalties, but it turns out you can make additional payments toward your current year taxes even after filing the extension. You can make additional payments online through EFTPS (Electronic Federal Tax Payment System) or by phone, and as long as the total of all your payments meets what you actually owe by the April deadline, you're good. Just make sure to specify it's for the current tax year when you make the payment. So even if you estimate conservatively and then realize you need to pay more, you're not stuck! This might give you some peace of mind as you're figuring out your numbers.

Has anyone used the "Pass-Through Entity" section in the Business Income area of TurboTax? I had similar issues last year and discovered that's where limited partnership entries need to be made, not in the regular Schedule E rental property section.

I had this exact same problem last year! The issue is that TurboTax has a confusing interface for partnership losses. You need to enter your K-1 information through the "Business Income" section, not the main Schedule E section that most people try to use first. Go to Federal > Income > Business Income > Partnership/S-Corp (K-1). Enter all the information from your K-1s there, including the passive loss amounts from Box 2 or Box 3. TurboTax will automatically flow these to the correct lines on Schedule E once you complete the K-1 entry process. Also, make sure you're not missing the "Passive Activity Loss" section if your losses exceed your passive income - TurboTax sometimes requires you to fill out additional forms for passive loss carryovers, and this isn't always obvious in the main workflow.

I work at a bank (not SOFI). Digital banks often have different processing schedules for ACH transfers compared to traditional banks. While the Federal Reserve might process the transaction on the DDD, it can take 1-3 additional business days for the receiving bank to post it. Since your DDD was Tuesday, and today is Friday, I'd say wait until Monday before assuming there's a problem.

I'm having the exact same issue with SOFI! My DDD was 3/18 and it's now 3/22 with no deposit. Called SOFI customer service yesterday and they said they're "processing" it but couldn't give me a timeline. It's so frustrating because my transcript shows the 846 code with the correct date and account number. At least I'm not alone in this - seems like SOFI is definitely holding these deposits longer than they should be. Going to give it until Tuesday like others suggested before escalating further.