Don't forget to call the IRS after sending important faxes to confirm they received them! I learned this the hard way when I faxed my offer in compromise docs and assumed they got them, only to find out 2 months later they had no record of receiving anything. Now I always follow up with a call about a week after sending anything critical.

Great advice from everyone here! I'd also add that if you're sending time-sensitive documents like amended returns or payment agreements, consider sending them through multiple channels (fax AND certified mail) for extra security. I've had situations where the IRS received one but not the other, and having both methods gave me backup proof of timely filing. Also, always keep your fax confirmation receipts - I scan mine and save them digitally with my tax files. The IRS can be slow to update their systems, so even if they received your fax, it might not show up in their records for several weeks when you call to check. One more tip: if you're faxing forms that require signatures, make sure your signatures are dark and clear on the scanned document. Light or blurry signatures can cause processing delays.

Does anyone know if the IRS is still doing that first-time penalty abatement I've heard about? I'm in almost the identical situation (unfiled 2022-2023, self-employed) and wondering if that could help me?

Victoria, I completely understand that crushing anxiety - I was in your exact shoes 18 months ago with unfiled returns from my freelance graphic design work. The panic attacks were real, but I promise you this is absolutely manageable. Here's your immediate action plan: **STEP 1:** Contact your bank ASAP and request detailed statements for 2022-2023. Most banks can provide up to 7 years of records. Also check any business banking apps, PayPal, Venmo, or Zelle for transaction histories. **STEP 2:** Reach out to clients you worked with during those years. Many will still have records of payments made to you, and some might even have copies of invoices you sent them. **STEP 3:** Check your email for ANY business-related correspondence - contract confirmations, payment notifications, expense receipts, travel bookings, etc. This can help reconstruct your business activities. **STEP 4:** File those returns IMMEDIATELY, even if incomplete. The failure-to-file penalty is much worse than failure-to-pay, and it stops accruing once you file. For penalties: You're likely looking at 5% per month (max 25%) for failure-to-file, plus 0.5% per month for failure-to-pay, plus interest. But if you qualify for first-time penalty abatement, you can get one year's penalties completely waived. The IRS has payment plan options if you can't pay everything at once. Don't let fear paralyze you - every day you wait, the penalties grow. You've got this!

Quick tip from someone who learned the hard way - even though you don't need to file 941 until you pay wages, you SHOULD file Form SS-4 to get your EIN as soon as you form your business entity. Having your EIN early makes everything easier when you do start hiring!

Great question! As others have mentioned, you don't need to file Form 941 until you actually start paying wages to employees. However, I'd suggest keeping detailed records of when you officially start your business operations, even if you're not paying wages yet. One thing that hasn't been mentioned is that if you do decide to pay yourself a salary from your business (rather than just taking owner draws), that's when Form 941 becomes required. This is especially important if you elect S-Corp tax status for your LLC - S-Corp owners who work in the business are required to pay themselves "reasonable compensation" as wages, which means you'd need to start filing Form 941. Also, make sure you understand the difference between employees and independent contractors from day one. Misclassifying workers is one of the most common mistakes new business owners make, and it can lead to back taxes and penalties on employment forms you didn't know you needed to file. Keep up the great work on staying compliant from the start - it'll save you headaches down the road!

Has anyone talked about Form 1041 yet? When my parent died with a trust, I had to file both their final personal tax return AND a tax return for the trust (Form 1041). The trust is its own tax entity.

I went through something very similar when my grandfather passed. The key thing that helped us was getting copies of all the original trust documents and any amendments to show the IRS exactly when assets were transferred and how the trust was structured. One thing to watch out for - if your father-in-law was both the grantor AND trustee of the irrevocable trust, the IRS might look more closely at whether it was truly irrevocable in practice. They sometimes argue that if someone retained too much control, it wasn't really separate from their personal assets. Also, definitely keep records of all those installment payments he made. If the IRS tries to claim interest or penalties accumulated after his death, you'll want proof of when payments stopped due to his passing. The debt doesn't keep growing once they're properly notified of the death. The good news is that with 15 years between trust creation and the tax issues, you're in a much stronger position than families who set up trusts after tax problems started.

Has anyone actually been audited over 1099-K stuff for selling personal items? I'm in a similar boat with some sports memorabilia I sold last year. My understanding is that personal items sold at a loss aren't even supposed to be reported - like if you sell your old laptop for less than you paid, that's not income or a deductible loss.

I'm dealing with a very similar situation with Pokemon cards I sold last year! Got a 1099-K for about $8K but definitely sold at a loss overall. One thing that helped me was creating a spreadsheet breaking down my collection by era and card type - I used a combination of PSA population reports and old price guides from when I originally bought the cards (many from the late 90s/early 2000s). For cards I couldn't find specific historical data on, I used the "replacement cost method" - basically what it would have cost to buy similar condition cards at the time I purchased them. I kept screenshots and printed documentation of everything I used as sources. The key thing my tax preparer told me was that the IRS expects "reasonable effort" not perfection, especially for collectibles purchased over many years. As long as you can show you made a good faith attempt to establish your basis using available data, you should be fine. Don't let the 1099-K stress you out too much - it's just a reporting document, not a tax bill!