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I've been dealing with similar inverse ETF wash sale questions and wanted to share what I learned from my tax attorney. The key factor the IRS looks at is whether the securities provide "substantially identical" economic exposure, not just whether they're technically different instruments. For your TSLS/Tesla puts situation, a few things work in your favor: inverse ETFs use derivatives and daily rebalancing which creates tracking differences from simple short exposure, put options have specific strike prices and expiration dates that create different risk profiles, and the leverage factor in TSLS (if any) versus unleveraged put options creates additional differentiation. However, be careful about the timing and magnitude. If you're buying at-the-money puts immediately after selling TSLS, you're in riskier territory than if you buy far OTM puts or wait even just a week or two. The IRS has been getting more sophisticated about these strategies, especially with the increase in ETF complexity. My attorney's advice was to document your investment thesis clearly - if you can show the puts serve a different purpose (like hedging a larger portfolio position rather than just replacing the inverse ETF exposure), that strengthens your position if questioned.
This is really helpful advice about documenting the investment thesis! I'm curious though - when you say "wait even just a week or two," does that actually provide meaningful protection under the wash sale rule? I thought the 30-day window was pretty rigid, so wouldn't waiting just 1-2 weeks still potentially trigger issues if the IRS considered the securities substantially identical? Also, regarding the leverage factor you mentioned - TSLS is actually a -1x inverse ETF (not leveraged), so it should track Tesla's inverse performance pretty closely on a daily basis. Would that make it more likely to be considered substantially identical to at-the-money puts, or do you think the derivative structure still provides enough differentiation?
You're absolutely right to question the timing aspect - the 30-day window is indeed rigid, and waiting just 1-2 weeks wouldn't provide any actual protection under the wash sale rule if the securities are deemed substantially identical. I should have been clearer about that. What I meant is that from a practical audit perspective, immediate replacement (same day or next day) tends to draw more scrutiny because it looks more obviously like you're trying to maintain the same economic position while claiming a loss. But you're correct that legally, day 1 and day 29 are treated the same if the securities are substantially identical. Regarding TSLS being -1x (unleveraged inverse), that does make the situation more complex since it should track Tesla's inverse performance quite closely. The daily rebalancing and derivative structure still create some differentiation, but you're right that at-the-money puts would have a more similar economic profile to a -1x inverse ETF than I initially suggested. Given that TSLS tracks so closely to inverse Tesla performance, I'd lean more toward the conservative approach - either wait the full 31 days or consider deep OTM puts that would behave very differently from the inverse ETF in most market conditions.
This is a really nuanced situation that highlights how complex modern tax planning has become with all the derivative instruments available today. Based on what I've seen from similar cases, the IRS tends to focus on the economic substance over the technical form when evaluating wash sales. Your TSLS position and Tesla puts both profit from Tesla declining, which could put you at risk even though they're mechanically different instruments. The fact that TSLS is unleveraged (-1x) makes it behave very similarly to being short Tesla, and at-the-money puts would have a similar delta exposure. A few practical suggestions: Consider puts that are significantly out-of-the-money (maybe 10-15% OTM) with longer expiration dates - these would have much different risk characteristics. Or you could look at puts on a different but correlated stock (like another EV company) to maintain some downside exposure to the sector without the direct Tesla connection. The conservative play would be waiting the full 31 days, but I understand not wanting to miss potential downside. If you do proceed immediately, make sure you document your reasoning for choosing puts over rebuilding the TSLS position (different expiration, strike price, portfolio hedging purpose, etc.) in case you ever need to justify the distinction. Have you considered consulting with a tax professional who specializes in securities transactions? Given the amounts involved with a 15% loss on an ETF position, it might be worth getting specific guidance for your situation.
Actually, the IRS absolutely does care about correct employer attribution! π Their matching system isn't just checking total income - it's verifying each specific W-2 against what employers reported. Think of it like your credit report - having the right total but wrong accounts would still be a problem. The good news is that since the total income is correct, this is a relatively simple amendment. Your preparer should file Form 1040-X showing the correct employer for each income amount. Since this doesn't change your tax liability, it's more of an administrative correction than a substantive one.
I believe it's worth noting that while this does require correction, the IRS may simply send a notice about the discrepancy rather than immediately demanding an amended return. If you receive such a notice, you should respond promptly with an explanation and supporting documentation. However, proactively filing an amendment is generally the safer approach to avoid potential complications down the line.
I completely understand your concern, especially with this being your first tax season filing separately after your divorce. The employer mismatch absolutely needs to be corrected - the IRS matching system will flag this even though your total income is accurate. Here's what you should do: Contact your tax preparer immediately and request they file Form 1040-X at no cost to you (since this was their error). Make sure to bring both W-2s and clearly show which income should be attributed to which employer. The amendment process typically takes 16-20 weeks, but since you're not changing your tax liability, there shouldn't be any penalties. Given your post-divorce situation, having accurate employer documentation is especially important for any potential support calculations or financial verifications you might need later. Don't let this stress you out too much - it's a common preparer error that's easily fixable!
As a tax preparer who's seen this exact scenario play out many times, I want to emphasize something that's been touched on but deserves more attention: the IRS has gotten much more sophisticated at detecting these patterns through automated systems. What you're describing - transferring assets just under the Kiddie Tax threshold to multiple children followed by quick sales - is essentially a textbook example of what their algorithms flag for review. Even if everything is technically legal, you're setting yourself up for scrutiny that's just not worth the minimal tax savings. I've had three clients in the past two years who tried variations of this strategy. All three ended up spending more on professional fees during their audits than they saved in taxes. The IRS agents specifically mentioned that custodial account activity is one of their focus areas right now. If you're really looking to reduce your tax burden while helping your kids, consider more straightforward approaches: 529 plans (as mentioned), direct educational expense payments (which don't count against gift limits), or even just holding the investments until you qualify for long-term capital gains rates. Sometimes the most boring strategy is also the smartest one.
This is really eye-opening information about the IRS algorithms flagging these patterns. As someone new to this community, I'm wondering - are there any other "clever" tax strategies that seem legitimate on the surface but are actually red flags for audits? It sounds like the key takeaway is that if something feels like you're trying to outsmart the system, it's probably not worth the risk. The peace of mind from using established, IRS-approved methods like 529 plans seems much more valuable than saving a few hundred dollars while risking an audit. Thank you to everyone who shared their real experiences - both the successes and the cautionary tales. This thread has been incredibly educational for someone just starting to think about tax optimization strategies.
New member here, but this discussion has been incredibly valuable as I was considering a very similar strategy for my two kids. The warning about IRS algorithms specifically flagging custodial account patterns is exactly what I needed to hear. I'm curious about one thing that hasn't been fully addressed - for those who mentioned 529 plans as the better alternative, are there any downsides to be aware of? I know the money has to be used for qualified education expenses, but what happens if my kids decide not to go to college or get full scholarships? Also, @CosmicCruiser mentioned that direct educational expense payments don't count against gift limits - could you elaborate on how that works? Does that mean I could pay tuition directly to the school without it counting against the annual gift tax exclusion? Thanks for saving me from what would have clearly been a mistake. Sometimes the "too good to be true" strategies really are just that.
Great questions! For 529 plans, there are a few downsides to consider: If your kids don't use the money for qualified education expenses, you'll pay a 10% penalty plus income tax on the earnings (not the principal). However, you do have options - you can change the beneficiary to another family member, use it for K-12 tuition (up to $10k/year), or even keep it for future grandchildren. Regarding direct educational payments - yes, that's correct! If you pay tuition directly to an educational institution, it's considered an unlimited gift tax exclusion and doesn't count against your annual $17,000 (for 2023) gift limit per person. This only applies to tuition though, not room and board or other expenses. So theoretically, you could pay $50,000 directly to a college for your child's tuition AND still give them the full annual gift allowance separately. As someone who also almost fell into the "too clever" trap, I've learned that the IRS has usually thought of these strategies before we have and has rules specifically designed to prevent them. The legitimate, boring approaches really do tend to be the most effective in the long run!
My parents pulled this same garbage with me. Here's what I learned: If you're under 24 and a full-time student, they CAN legally claim you as a dependent, BUT that doesn't mean they own your refund!! The refund is based on YOUR income and YOUR withheld taxes. Next year, file your own taxes ASAP before your parents can. You can still mark that "someone can claim you as a dependent" but YOU control where the refund goes. For this year, unfortunately, it might be a matter of family negotiation rather than legal action. The IRS won't get involved in family disputes even if you're technically right.
This is the correct answer. I work part time at an accounting office during tax season and see this all the time. Parents think that claiming their kid as a dependent means they're entitled to the kid's refund too, but that's not how it works.
I'm really sorry you're dealing with this frustrating situation. As others have mentioned, legally that refund belongs to you since it's from taxes withheld on YOUR earnings. Being claimed as a dependent doesn't give your mom ownership of your refund. That said, since she already has the money deposited in her account, your best options are probably: 1) Having a calm conversation about splitting it fairly - maybe contributing some toward household expenses but keeping money for your textbooks and car repairs, or 2) Making sure you file your own taxes next year before she can. For next year, open your own bank account if you don't have one already, and file as soon as you get your W-2. You can still check the box that says someone can claim you as a dependent, but YOU control where your refund goes. I know it's tough when it's family, but you worked for that money and you deserve to have control over it. Try approaching the conversation from a "fairness" angle rather than making it confrontational - maybe suggest keeping 60-70% for your school/car needs while contributing the rest to household expenses.
Chloe Martin
Does anyone know if TaxAct handles the home sale exclusion the same way as TurboTax? I'm in a similar situation but using different software.
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Diego FernΓ‘ndez
β’I used TaxAct last year for my home sale. It works similarly - there's a section for real estate transactions where you'll enter all your info. It will calculate if you qualify for the exclusion automatically. The interface is different but it asks all the same questions about purchase date, sale date, improvements, etc.
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Layla Mendes
@Hiroshi, based on your situation, you should be in great shape! With 6+ years of primary residence and only $78k in profit, you're well under the $500k exclusion limit for married filing jointly. In TurboTax, look for the "Federal Taxes" section, then "Wages & Income," and you should see "Investment Income" or "Less Common Income." There will be a section for "Stocks, Mutual Funds, Bonds, Other" - click "Start" there and look for "Sale of Your Home" or similar wording. The software will ask you about: - Purchase date and price - Sale date and price - Any major improvements you made - How long you lived there as primary residence Don't stress about finding a separate "worksheet" - TurboTax handles all the calculations behind the scenes using Forms 8949 and Schedule D. Just answer their questions honestly and the software will automatically apply the Section 121 exclusion. One tip: gather receipts for any major home improvements you made over those 6 years (new HVAC, kitchen remodel, roof, flooring, etc.) as these increase your basis and further reduce any potential taxable gain, though you likely won't need them given your numbers. You've got this! The exclusion was designed for exactly your situation.
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GalaxyGlider
β’This is really helpful! I'm in a similar boat - sold my home after living there for 4 years and made about $65k profit. One question though: when you mention gathering receipts for major improvements, how far back should I go? I have some receipts from 2019 but others I might have lost. Will the IRS accept bank statements or credit card statements as proof if I don't have the original contractor invoices?
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