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Ask the community...

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Connor Rupert

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Just wanted to add something important that hasn't been mentioned yet. When you're dealing with after-tax funds in a SEP IRA that were never reported, you need to be careful about the statute of limitations. Generally, the IRS has 3 years to audit your returns, but this can be extended in certain situations. In your case, since these contributions weren't reported at all, you might want to consult with a tax professional about any potential risks before proceeding with the conversion. Also, make sure you have documentation of those original contributions from 7 years ago - bank statements showing the transfers to the SEP, etc. The more documentation you have to support your claim that these were after-tax contributions, the better off you'll be if there are any questions.

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Thanks for bringing this up - I hadn't considered the statute of limitations angle. Do you think filing the Form 8606 now for those old contributions might trigger some kind of review of those past tax years?

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Connor Rupert

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Filing Form 8606 now for old contributions typically doesn't automatically trigger an audit, but it does put those years on the IRS's radar. The good news is that you're trying to comply with the rules by properly documenting your basis in the IRA, which looks better than if they discovered the unreported contributions some other way. The key is documentation - make sure you have records of all those contributions and be prepared to show they were made with after-tax dollars. If you're concerned, working with a tax professional who specializes in IRA issues might be worth the investment to ensure everything is handled properly and to help respond if the IRS does have questions.

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Molly Hansen

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Has anybody considered that the OP could potentially benefit from the losses in the SEP IRA? If the original contributions were $60k and current value is $38k, that's a significant loss. While you can't typically deduct IRA losses, if you liquidate ALL your IRAs (of the same type) and the total distribution is less than your basis, you might be able to claim the loss as a miscellaneous itemized deduction subject to the 2% AGI floor. Though I believe this was suspended under the TCJA until 2026.

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Brady Clean

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This is incorrect information. The Tax Cuts and Jobs Act eliminated the deduction for IRA losses completely through 2025. Even before that, claiming such losses was extremely difficult and rarely beneficial due to the AGI limitations. Please don't give tax advice if you're not certain - it could cause serious problems for the OP.

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My understanding is that there are some rare exceptions to the 90-day deadline for Tax Court petitions. I think they're called "equitable tolling" situations. If you had some extraordinary circumstance like being in the hospital or deployed in the military, it might be worth mentioning that in a follow-up to the Tax Court.

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Jessica Nolan

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That's interesting. I didn't have any extreme circumstances like that though. Just poor planning and procrastination on my part unfortunately. Do you know if the IRS ever just "forgives" these situations if I explain it was an honest mistake?

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The IRS generally doesn't "forgive" missed deadlines just because it was an honest mistake. They hear that all the time. If it was truly just procrastination, you'll need to follow the pay-first-then-claim-refund route the others mentioned. However, there was actually a recent Supreme Court case (Boechler v. Commissioner) that established equitable tolling could apply for certain tax deadlines, though that was for Collection Due Process cases, not deficiency notices. Still, tax law continues to evolve on these issues.

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Amaya Watson

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Has anyone dealt with amended returns being processed during this type of situation? I filed an amended return like OP did and I'm wondering how long it typically takes the IRS to process those compared to regular returns?

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Grant Vikers

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In my experience, amended returns are taking FOREVER right now - like 6+ months. I filed one in April and it's still "processing" according to Where's My Amended Return tool. But that's separate from the Tax Court deadline issue. The amended return won't stop the deficiency assessment if you missed the petition deadline.

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Schedule C, Fillable Forms & Self-Employment - Sanity Checks for Year 2 Filing (W2 + Business)

Hey fellow tax survivors! I'm in my second year using free fillable forms and my first year with a side business (while still working a W2 job), and I'm hoping for some validation on a few things. Just need to make sure I'm not screwing anything up royally. My situation: I've got regular W2 income from my day job, started a small business last year that's making some profit, have an HDHP with HSA contributions, and a bit of interest income from my savings. I've figured out my first question on my own (it was about Schedule SE Line 2 and Schedule K-1 Form 1065), but I'm still stuck on these: 2) On Form 8995A (Qualified Business Income Deduction), line 4 asks for "Allocable share of W-2 wages from the trade, business, or aggregation." I'm completely lost here. I understand it relates to the limit being "the lesser of 20% of total 1040 taxable income" from what I've read, but I'm not sure what to enter. My total 1040 taxable income? Just my business profit? (But that's not W2 income, right?) If I put 0, all the calculation lines show 0, which doesn't seem right based on what I know about the QBI deduction. Really confused about this one! 3) Based on my situation, here are the forms I think I need to file. Am I missing anything important? - Form 1040 (obviously) - Schedule 3 (for prepayments) - Form 8889 (for HSA) - Schedule B (for interest/bank bonuses) - Schedule C (business profit) - W-2 (employment income) - Form 8995A (QBI deduction) - Schedule SE (self-employment tax) Any help would be super appreciated! I'm trying to avoid making expensive mistakes.

Just wanted to add that if you're using Schedule C and Form 8995A, don't forget about the Section 199A deduction which is related to your Qualified Business Income. It's basically a 20% deduction on your net business income if you're below those income thresholds someone mentioned. Also, since you have HSA contributions with an HDHP, make absolutely sure you're maximizing that! For 2024, you can contribute up to $4,150 for individual coverage or $8,300 for family coverage (plus $1,000 catch-up if you're 55+). This is literally the best tax advantage available - it goes in pre-tax and comes out tax-free for medical expenses.

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Khalid Howes

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Thanks for the reminder about the Section 199A deduction! Is that handled automatically through Form 8995A or do I need to do something else to claim it? For the HSA, I'm contributing the maximum for individual coverage. One question though - if I switch to family coverage mid-year, can I contribute the full family amount or is it prorated?

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Form 8995A is specifically for calculating your Section 199A (Qualified Business Income) deduction, so no need to do anything additional. It flows automatically to your 1040. For HSA contributions after switching to family coverage mid-year, it gets a bit complicated. You can actually contribute the full family maximum ($8,300 for 2024) if you're still covered by a family HDHP on December 1st and remain covered for the full calendar year of 2025 (called the "last-month rule"). If you don't maintain coverage through December 2025, you'd need to prorate your contribution based on how many months you had each type of coverage.

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Kara Yoshida

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Don't forget that your self-employment tax (Schedule SE) is based on 92.35% of your net earnings from self-employment, not the full amount! This trips up a lot of first-timers. The reason is that employees only pay half of FICA taxes while employers pay the other half, but self-employed people pay both halves. The 7.65% reduction compensates for this. Also, you can deduct half of your self-employment tax on Schedule 1, line 15. This is an adjustment to income, so you get this deduction even if you don't itemize.

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Philip Cowan

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Just a quick correction - the SE tax is actually 15.3% (12.4% Social Security + 2.9% Medicare) on that 92.35% of net earnings, up to the Social Security wage base limit ($168,600 for 2024). Then 2.9% Medicare tax continues beyond that with no limit, plus an additional 0.9% for high earners. But your point about deducting half on Schedule 1 is super important - loads of people miss that and it's a significant deduction!

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Zane Gray

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One thing to be careful about with Section 1231 gains is the "look back rule." If you had any 1231 losses in the previous 5 years, your current 1231 gains are treated as ordinary income to the extent of those prior losses. This could affect whether your full gain qualifies for OZ treatment. Also, remember that even though you can defer the tax until 2026, you'll eventually have to pay it. Make sure you'll have the liquidity to pay that tax bill when it comes due, since it's not forgiven - just deferred.

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Tasia Synder

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Thanks for bringing up the look-back rule - I hadn't considered that! I do have a small 1231 loss from a property I sold in 2023. So if I understand correctly, a portion of my current gain would be considered ordinary income rather than capital gain? Would that portion not be eligible for OZ investment?

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Zane Gray

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Yes, exactly. If you had a 1231 loss in 2023, a portion of your current 1231 gain would be recaptured as ordinary income to the extent of that previous loss. That recaptured portion would not be eligible for OZ investment, since OZ investments can only be made with capital gains. For example, if you had a $10,000 1231 loss in 2023 and now have a $50,000 1231 gain, $10,000 of your current gain would be treated as ordinary income and only the remaining $40,000 would be treated as capital gain eligible for OZ investment.

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Has anyone here actually invested in an OZ fund? I'm considering it but worried about limited options and high fees. Most of the funds I've looked at have 2% management fees plus performance fees, which seems high.

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I invested in an OZ fund after selling a small apartment building in 2022. The fees are definitely higher than typical investment funds, but remember you're getting tax benefits that can offset those costs. I went with a fund focused on multifamily development in emerging markets which aligned with my investment goals. Make sure you do due diligence on the fund manager's track record and understand the timeline - you need to hold for 10+ years to get the full tax benefits on appreciation. And be prepared for the tax bill in 2026 on your initial deferred gain.

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Liam Cortez

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Another strategy that worked for our family C-Corp was implementing a qualified retirement plan to shift some of the accumulated earnings. By setting up a substantial defined benefit plan, we were able to make large, tax-deductible contributions that decreased our retained earnings while building wealth in a tax-advantaged environment. This approach served two purposes - reducing the accumulated earnings that might trigger AET while also creating a legitimate business purpose for some of our accumulations (funding future retirement plan obligations).

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Savannah Vin

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Interesting approach! Approximately what percentage of your annual earnings were you able to shift this way? And did you face any challenges with the IRS regarding the size of the contributions relative to employee compensation?

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Liam Cortez

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We were able to shift around 15-20% of our annual earnings through the defined benefit plan. The exact amount depends on factors like age, compensation levels, and retirement age assumptions, but it made a meaningful difference in our accumulated earnings position. We haven't faced IRS challenges because we worked with an actuary to ensure our contributions were justifiable based on legitimate factors like age and compensation. The key is ensuring the plan is properly designed as a genuine retirement vehicle, not just a tax avoidance mechanism. Having multiple real employees (not just family members) participating in the plan also helps demonstrate its legitimacy.

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Mason Stone

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Has anyone considered using offshore structures for this? I heard some wealth advisors talking about foreign holding companies as a way to manage passive investments.

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Lauren Wood

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I strongly advise against offshore structures for avoiding PHC or AET taxes. The IRS has extremely robust anti-avoidance rules for foreign corporations owned by US persons. You'll trigger Controlled Foreign Corporation (CFC) rules, GILTI (Global Intangible Low-Taxed Income) taxes, PFIC (Passive Foreign Investment Company) regulations, and face extensive foreign reporting requirements with massive penalties for non-compliance. The compliance costs alone would likely exceed any theoretical tax benefits, and aggressive offshore structures specifically designed for tax avoidance could trigger significant penalties or even criminal charges.

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