Just chiming in to add my experience as someone who didn't file for 5 years (2016-2020) and finally caught up last year. The biggest surprise was that I was actually OWED money for 3 of those 5 years because I had too much withheld from my paychecks! Unfortunately I could only get refunds for 2020 since the others were outside the 3-year window, but I was relieved there were no penalties since I was due refunds. The peace of mind from being caught up is worth it even though I lost out on some refund money. Whether you should file really depends on if you had taxes withheld that were more than what you would have owed. If you were a W-2 employee with normal withholding, there's a decent chance you're owed money rather than owing the IRS.

Gabriel, I can definitely understand your stress about this! From what you've shared, you're actually in a pretty good position since you've gotten current with 2021-2023. Here's my take on your specific situation: Since you're primarily concerned about FAFSA eligibility for January, you should be fine. FAFSA typically uses the "prior-prior year" tax information, so for starting school in January 2025, they'll likely want your 2023 return (which you have filed). However, I'd still lean toward filing those back years (2017-2020) for a few reasons: 1. You mentioned wanting peace of mind - unfiled returns can create anxiety that lingers 2. If you were a W-2 employee during those years, there's a decent chance you're owed refunds (especially for 2020, which you might still be able to claim) 3. It eliminates any future complications if you need tax transcripts for loans, employment background checks, or other purposes Before spending money on a tax preparer though, I'd suggest trying to figure out if you were even required to file for those years. If your income was below the filing threshold for any of those years, you wouldn't need to file at all. You can check the IRS website for historical filing thresholds by year. The fact that your current tax preparer seemed confused suggests he might not specialize in back tax situations - you might want to consult with someone who has more experience with unfiled returns to get a clearer picture of your obligations and potential refunds.

Sometimes the IRS mail just gets lost too. The USPS in my area has been terrible lately. I'd proceed as if you're enrolled and take steps to opt out rather than waiting for a letter that might never come.

Check your IRS online account at irs.gov - you can see your CTC enrollment status there without needing the letter. If you're enrolled, there's an "unenroll" or "opt out" option right in the portal. I had the same issue last year where I never got the physical notice but could handle everything online. Just make sure to do it before the deadline mentioned above!

Have you noticed how the IRS seems to release refunds in batches by filing date? I filed on January 29th and got my DDD for 2/19, received via Chime on 2/17. My brother filed February 1st and got his DDD for 2/26 - same batch as you. Seems like they're processing weekly batches for straightforward returns. Did anyone who filed in early February get a different DDD than 2/26? Or is the pattern holding?

I'm in the same boat as you! Filed on January 31st and just got my DDD for 2/26 too. Still waiting for it to hit my Chase account though - looks like I'll be one of those traditional bank folks waiting until the actual date. It's interesting how consistent the IRS batching seems to be this year. I'm curious if anyone with Credit Karma Money or Current has seen early releases like Chime? Those neo-banks usually follow similar early release policies.

Has anyone experienced Robinhood being late with their 1099s? Last year they said mid-February but I didn't get mine until almost March 1st!

I'm dealing with a similar situation and wanted to share what I learned from calling my tax preparer. They told me that crypto platforms like Robinhood often have slightly different cost basis calculations than what you might track manually, especially if you made multiple buys and sells of the same crypto. The 1099-B will show the "proceeds" (what you received when you sold) and the "cost basis" (what the platform calculated you originally paid). Sometimes their wash sale adjustments or FIFO/LIFO calculations can be different from your spreadsheet. My advice would be to wait for the official forms. I know it's tempting to file early, especially with all those TurboTax reminders, but the peace of mind is worth the extra few weeks. Plus, if you're getting a refund, the IRS processes returns pretty quickly once they start accepting them in late January anyway. One thing that might help - you can set up an account on the IRS website and check if Robinhood has already submitted your 1099 information electronically, even before you receive the physical/electronic copy.

8 Has anyone used TurboTax to handle a 1099-C situation? I got one too and have no idea where to even report this in the software.

This sounds really frustrating! I had a similar situation last year where I got a 1099-C that didn't make sense at first. A few things to check: First, look at the creditor name on the 1099-C - sometimes it's not the original credit card company but a debt buyer or collection agency that you might not recognize. The "medical" categorization could be because you used that credit card for medical expenses at some point, even if it wasn't exclusively for medical purposes. Also, double-check your records to make sure you paid the full original balance and not a settled amount. Sometimes people think they paid in full but actually accepted a settlement offer without realizing it. If you're certain you paid the debt in full, you'll want to dispute this with the issuing creditor. Get documentation of your payment and request they issue a corrected 1099-C. In the meantime, you might need to report it on your taxes but include a statement explaining the situation until you get it resolved. Keep all your payment records handy - you'll likely need them whether you're disputing with the creditor or explaining to the IRS.