Slightly different perspective - have you checked if you might qualify for the reduced 50% exclusion rather than the 100% exclusion? The rules vary based on when the stock was acquired as C corp shares. For C corp shares acquired after August 10, 1993 but before February 18, 2009, you can exclude 50% of the gain. For shares acquired after February 18, 2009 and before September 28, 2010, you can exclude 75%. And for shares acquired after September 28, 2010, you can exclude 100%. But this all depends on when the shares were acquired as C corp shares, which in your case sounds like October 2018, so you'd be in the 100% category if you met the holding period.

I'm really sorry to hear about your situation - being just two months short of the 5-year requirement is incredibly frustrating, especially when you've been with the company since its founding. While the other commenters are correct about the general rule that C-Corp holding periods don't "tack" from previous entity types, there might be one avenue worth exploring given your specific timeline. Since your S-Corp to C-Corp conversion happened in October 2018, you should definitely investigate whether this qualified as a tax-free reorganization under Section 368 of the Internal Revenue Code. If the conversion was properly structured as a Section 368 reorganization (which many S-Corp to C-Corp conversions are), there's potentially an argument for holding period tacking under certain circumstances. This is an extremely technical area of tax law where the specific documentation and structure of your conversion matters enormously. Given the potential tax savings at stake, I'd strongly recommend consulting with a tax attorney who specializes specifically in Section 1202 and corporate reorganizations - not just a general CPA. You'll need someone who can review your conversion documents, operating agreements, and any legal opinions from 2018 to determine if there's any path forward. The fact that you were kept in the dark about sale details is also concerning from a fiduciary duty standpoint, but that's a separate issue. For now, focus on gathering all your corporate documents from the 2018 conversion and get specialized legal advice before your filing deadline.

Watch out for the once-per-year rollover rule too! If you've done any other IRA rollovers within the past 12 months, you might not be eligible to correct this through a standard rollover. This tripped me up badly with my dad's estate. The good news is that trustee-to-trustee transfers don't count toward this limit. But if what happened was the trustee distributed the money to the trust account first (not directly to another IRA custodian), you're dealing with a rollover situation and that one-per-year limit applies.

I'm dealing with something similar right now and wanted to share what I've learned so far. The distinction between "transfer" and "rollover" is crucial here - a transfer should happen directly between custodians without the money ever touching your hands or the trust account, while a rollover involves you receiving the distribution and then redepositing it within 60 days. If the trustee actually received the IRA funds into the trust account instead of doing a direct custodian-to-custodian transfer, that's definitely a taxable event. But there might still be hope! I've been researching Revenue Procedure 2020-46 (which updated the 2016 version mentioned earlier) and it does provide relief for certain trustee errors. The key is proving this was the trustee's mistake, not a choice you made. Get documentation from them ASAP admitting they processed this incorrectly. Also, check exactly when this happened - if it's been less than 60 days, you might still be able to do an indirect rollover to fix it. One thing that's been helpful for me is keeping a detailed timeline of all communications with the trustee. The IRS wants to see that you acted reasonably and that this wasn't intentional tax avoidance. Good luck - these trust/IRA situations are incredibly confusing but there are usually options available!

My partner and I did this 3 years ago! One tip: consider putting only one person on the mortgage but both on the deed if your bank allows it. That way, only one person claims all the interest but both have ownership. We did this bc my credit score was way better so I got the loan alone (better rate!) but we're both on the deed. The person not on the mortgage can just transfer their share of the payment to the mortgage holder, who then makes the full payment and claims 100% of the deduction. Simplifies taxes a lot! But u need to trust each other obvs.

Great question! I went through this exact situation two years ago when my partner and I bought our first home. Here's what I learned from working with both a tax professional and mortgage lender: Since you're both on the mortgage and splitting payments 50/50, you can each deduct your proportional share of the mortgage interest on your individual tax returns. Keep detailed records of who pays what - bank statements, cancelled checks, or electronic transfer records showing each person's contribution. One key thing to watch out for: the mortgage lender will send ONE Form 1098 (mortgage interest statement) to whoever is listed as the primary borrower. You'll need to coordinate to ensure you both get the information needed for your tax returns. Some couples scan and share the 1098, others request the lender send copies to both parties. Also, don't forget about property taxes! If you're splitting those 50/50 as well, you can each deduct your portion of property taxes paid, which also goes on Schedule A. Given your combined income of $180k and a $520k mortgage, you'll likely have enough deductions to make itemizing worthwhile. The mortgage interest alone in your first few years will probably exceed the standard deduction threshold. One last tip: consider having a tax pro review your first year's return to make sure you're handling everything correctly. It's worth the cost to get it right from the start!

When I won on a Canadian game show (different one, smaller prize), they actually withheld Canadian taxes first, then I had to report it in the US. But I got a foreign tax credit for the Canadian taxes paid, so I didn't end up paying double. Make sure your cousin keeps ALL documentation they gave her. Also, if this aired on TV, keep a copy of the episode if possible as proof if ever questioned.

Your cousin should also be prepared for this to potentially affect her state taxes in Massachusetts. Game show winnings are typically subject to state income tax as well, so she'll need to report the $25,000 on her Massachusetts return too. One more thing - if the show hasn't aired yet, she might want to consider making quarterly estimated tax payments now rather than waiting until next year's filing deadline. Owing $25k worth of additional taxable income could result in a significant tax bill, and the IRS charges underpayment penalties if you don't pay enough throughout the year. She can calculate roughly what she'll owe using her current tax bracket and make payments using Form 1040ES. The safe harbor rule is to pay at least 90% of this year's tax liability or 100% of last year's (110% if her previous year's AGI was over $150k). Since this is unexpected income, making an estimated payment could save her from penalties later.

Did you claim any credits like EIC or Child Tax Credit? Those automatically get extra scrutiny and slow down processing.

I'm in a very similar situation - filed on March 8th and still getting that same "processing delayed" message with Tax Topic 152. My transcript has been completely blank for 7 weeks now. What's really frustrating is that I had a simple return too - just W2 income, standard deduction, no credits or complications. I've been checking the WMR tool almost daily and it's maddening to see the same message over and over. Like you, I'm starting to wonder if something went wrong or if my return got lost in the system somehow. The fact that the transcript shows absolutely nothing is what worries me most. Reading through these comments has been really helpful though - especially learning about ERS (Error Resolution System) from the former IRS employee. At least now I understand this is unfortunately normal for this filing season, even though it's incredibly stressful when you're waiting on your refund. I think I'm going to wait until I hit the 8-week mark before trying to call, based on the advice here. The phone situation sounds absolutely brutal right now. Has anyone had success getting through recently, or is it still basically impossible?