Has anyone actually been fined for this? My dad's been preparing taxes for 30+ years and still does paper filing for about half his clients (probably 150+ returns). He's never had an issue with the IRS about it.

This is a really important issue that more tax preparers need to take seriously. I work at a mid-size CPA firm and we went through this exact transition about 3 years ago when our managing partner finally realized we were at risk. The key thing to understand is that the IRS penalty of $50 per return might seem small, but it's assessed PER RETURN that should have been e-filed. So if your firm prepares 200+ returns annually and has been paper filing for several years, you're looking at potentially tens of thousands in penalties if they decide to audit your compliance. What really convinced our managing partner was when I calculated that we were spending about 15-20 extra minutes per return on paper filing (printing, mailing, tracking) compared to e-filing. Once you factor in postage costs and staff time, e-filing actually saves money even without considering the penalty risk. My suggestion would be to prepare a business case showing both the financial risk of continued non-compliance AND the efficiency benefits of switching. Most old-school preparers resist change because they think it'll be more complicated, but modern e-filing software is actually much easier than the paper process once you get set up. The IRS has definitely been stepping up enforcement - we've seen several local preparers get hit with compliance reviews in the past two years. It's really not worth the risk when the solution is so straightforward.

I'm currently waiting for my STPG cashier's check as well and this thread has been incredibly helpful! My tax preparer told me to expect it by April 15th, but after reading everyone's experiences, I'm cautiously optimistic it might arrive a few days earlier. One thing I've learned from previous years is to make sure your mailing address with your tax preparer is exactly correct - I had a friend whose check was delayed because of a small address discrepancy. Also, for anyone still waiting, I've found that the STPG portal updates seem to happen in batches, so don't panic if the status doesn't change immediately. Thanks to everyone who shared their timelines and tips about contacting customer service through tax preparers - definitely keeping that in mind if I don't see my check by the expected date!

I'm currently going through this exact situation! My tax preparer used STPG and gave me an expected date of April 18th for my cashier's check. Reading through all these experiences has been really eye-opening - it sounds like there's a decent chance it could arrive a few days early, which would be amazing. I'm particularly interested in what @Miguel Silva mentioned about the 5-7 business day timeline after STPG shows "funds received" on their portal. My portal still shows "processing" so I'm guessing the IRS hasn't released my funds to them yet. One question for those who've been through this - do you get any kind of email notification when STPG actually mails out your check, or do you just have to keep checking the portal and your mailbox? This is my first year using the cashier's check option instead of direct deposit, and the waiting is definitely more nerve-wracking than I expected! Also planning to double-check my mailing address with my preparer tomorrow after reading about potential delays from address issues. Thanks everyone for sharing your experiences - it's really helpful to know what to expect!

10 Quick question - does anyone know if student loan debt counts as a liability for the insolvency calculation? I have about $45k in federal student loans that were in deferment when my debt was canceled.

This is really helpful information! I'm dealing with a similar situation where the IRS is claiming I owe taxes on discharged debt from a few years ago. Your insolvency calculation looks solid - the fact that your liabilities exceeded your assets by $20,000 when the $15,500 debt was canceled should definitely qualify you for the full exclusion. One thing I learned from my tax preparer is to make sure you're using fair market values for your assets, not what you originally paid. So for your home and car, use the actual market value on the date the debt was canceled, not the purchase price. Also double-check that you included ALL liabilities - credit cards, student loans, any outstanding bills, etc. The documentation is key. I'd recommend creating a detailed spreadsheet showing every asset and liability with supporting documentation. The IRS loves paper trails, so bank statements, property records, loan statements - anything that backs up your numbers will help your case.

Hey, are you using TurboTax by any chance? I ran into that EXACT SAME ISSUE last week. The solution was to go to Forms Mode (you can search for it in the search bar at the top), then find Form 2210, and there's a checkbox that says "I didn't file this form last year" - check that and the software will stop asking for the missing info! Also, just a heads up that when you switch from MFJ to MFS, some of your deductions will be different. Make sure both of you don't claim the same credits for the kids. And double check your student loan interest deduction - when filing MFS, you usually can't claim that deduction (though the payment benefits might still make MFS worth it).

I had this exact same issue when I switched from MFJ to MFS three years ago! The tax software kept insisting I needed Form 2210 data from the previous year even though we'd never filed one. Here's what worked for me: First, double-check your 2022 return by searching the PDF for "2210" like others mentioned. If it's not there, you're good. Then in your tax software, look for an "interview mode" or "easy step" option and switch it OFF - go to the more detailed/advanced mode instead. This usually gives you more control over these yes/no questions. In the advanced mode, when it asks about Form 2210, there should be a clear "No, I did not file this form" option rather than just trying to skip past it. If you're still stuck, try starting a completely fresh return in the software and being very deliberate about answering "No" to the Form 2210 question the first time it appears. One more tip - make sure you're entering your 2022 AGI correctly from your actual tax return (not from memory). Sometimes the software gets confused if there's a mismatch and starts asking for forms you didn't file. Good luck finishing up before your extension deadline!

After reading all this, I'm genuinely curious - has anyone successfully used the 65-day rule to reduce trust taxes? My accountant mentioned it but wasn't sure if it was worth the effort for our situation.

This is incredibly helpful information! I'm dealing with a similar trust situation for my nephew and had no idea about the 65-day rule or the DNI calculations. One question - when you pay the taxes from the trust accounts, do you need any special documentation for the investment companies? I'm worried about how to properly record the tax payments as trust expenses versus personal expenses when I'm writing checks from the trust account. Also, has anyone dealt with estimated quarterly payments for trusts? I'm wondering if I should be making those going forward since we'll likely have similar investment income each year.