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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.
This is a good point, but the exclusion percentages only matter if OP meets the 5-year holding requirement first, which seems to be the main issue here. Being 2 months short of 5 years means they likely can't access any of the exclusion percentages.
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.
This is exactly the kind of detailed advice I was hoping for. You're right that being kept out of the sale discussions was problematic on multiple levels, but I need to focus on the tax implications first since the filing deadline is approaching. I'm going to dig through all the 2018 conversion paperwork this weekend. My co-founder who handled the legal work has been difficult to work with, but I think I can get the documents from our corporate attorney directly. Do you happen to know what specific language or provisions I should be looking for in the documents that would indicate it was structured as a Section 368 reorganization? Also, given how specialized this area is, do you have any recommendations for finding attorneys who specifically handle Section 1202 cases? Most of the tax attorneys I've found seem to focus on more general corporate tax issues.
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.
Does the once-per-year rule apply to inherited IRAs though? I thought those had different rules.
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!
This is really helpful - thank you for breaking down the transfer vs rollover distinction so clearly! I'm completely new to this and honestly didn't even know there was a difference. One question - you mentioned getting documentation from the trustee admitting they made a mistake. Should I be asking for something specific in writing, or just any acknowledgment that they processed it wrong? I'm worried about how to phrase this request without making them defensive or unwilling to help fix the situation. Also, when you say "indirect rollover," does that mean I would need to have the actual cash available to redeposit? Because if taxes were already withheld from the distribution, I'm not sure I'd have the full original amount to put back in.
Great questions! For the documentation, you want something in writing that specifically states they failed to follow proper IRA distribution procedures. I'd suggest asking for a letter that says something like "We acknowledge that the IRA distribution from [Trust Name] on [Date] was processed as a direct distribution rather than the intended direct trustee-to-trustee transfer." Don't worry about making them defensive - this is actually a liability issue for them too, so most trustees will cooperate once they understand the tax implications. Regarding the indirect rollover and withholding - this is where it gets tricky. Yes, you'd need to deposit the full original IRA amount, even if taxes were withheld. So if the IRA was worth $100,000 but they withheld $20,000 for taxes, you'd still need to deposit the full $100,000 to avoid taxation on the $20,000 shortfall. You'd then claim the withheld amount as a credit when you file your tax return. This is exactly why the Revenue Procedure waiver route might be better than trying to do an indirect rollover - it can potentially undo the whole mess without requiring you to come up with extra cash. Definitely worth exploring both options with the IRS directly.
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.
Isn't that technically mortgage fraud? I thought the person claiming the deduction has to be legally responsible for the debt. If only one person is on the mortgage, can they really claim 100% even if the other person is paying half?
Just a warning - I tried doing this exact arrangement and it backfired on me. When my partner and I split, I had no legal right to the mortgage interest deductions despite paying half the mortgage for years. Also created huge issues when we sold since I was on the deed but not the mortgage. Would not recommend.
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!
This is really helpful advice! Quick question about the Form 1098 - if the lender only sends it to the primary borrower, do we need to do anything special to make sure the IRS knows we're each claiming our portion? Or is it enough that we each report our share on our individual Schedule A forms? I want to make sure we don't accidentally trigger any red flags by both claiming parts of the same 1098.
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.
This is really helpful advice about the estimated payments! I'm new to understanding tax obligations and wondering - when you mention the safe harbor rule, does that 90% calculation include this new prize income, or is it based on her regular job income? Like if she normally makes $50k from her job and now has this extra $25k, what exactly would she need to calculate for the estimated payment?
Anna Stewart
That's a fantastic study plan revision, Emma! It sounds like you've really taken the advice to heart and created a comprehensive approach. One additional tip I'd suggest - since you mentioned you're juggling this with family life, consider setting up a study tracking spreadsheet or app to monitor your progress across all these different methods. It helps you see which areas need more attention and keeps you motivated when you can visually see your improvement. Also, since you're scheduled for January 5th, make sure to take a full-length practice exam under timed conditions about 2-3 weeks before your test date. This will help you identify any remaining weak spots and get comfortable with the exam format and timing. The real exam can feel quite different from doing scattered practice questions. Best of luck with your EA journey - your dedication and willingness to adapt your approach based on feedback shows you're going to do great!
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Madeline Blaze
ā¢Great advice about the practice exam timing, Anna! I'm new to this community but have been lurking and reading everyone's tips. Just wanted to add that when you do take that full-length practice exam, try to simulate the actual testing conditions as closely as possible - same time of day, same room setup if possible, and definitely turn off your phone. I learned this the hard way when I took my first practice test at home with all the usual distractions and then felt completely thrown off by the quiet testing center environment. The adjustment was harder than I expected! Emma, your revised plan looks amazing - you're definitely setting yourself up for success.
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Amina Diop
Welcome to the community, Emma! Your study plan sounds really solid, especially with the deadline motivation of having your exam scheduled for January 5th. One thing I'd add to all the excellent advice you've received - consider creating a "mistake log" as you work through practice questions. Write down not just what you got wrong, but WHY you got it wrong (misread the question, didn't know the rule, calculation error, etc.). This helped me identify patterns in my mistakes that I could then specifically address. Also, since you're multitasking with the audio content while with your kids, you might want to designate certain "focus topics" for those listening sessions vs. others. I found that simpler review material worked better during multitasking time, while I needed full concentration for complex topics like depreciation rules or partnership taxation. The fact that you're already thinking strategically about your approach and willing to adjust based on feedback tells me you're going to do great. The EA exam is challenging but very passable with the right preparation. Keep us posted on how your studying goes!
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