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Has anyone had experience with options that aren't clearly Section 1256 contracts? I have some foreign index options and I'm not sure if they qualify for the 60/40 treatment or if they're just regular capital assets.
Only options on "broad-based" indices qualify as Section 1256 contracts. Foreign indices generally don't qualify unless they're specifically listed by the IRS. If your foreign index has fewer than 10 stocks or if the options aren't regulated by the CFTC, they're probably just regular capital assets with standard short/long term treatment.
I went through this exact same headache last year with SPX spreads that crossed tax years. The key insight that finally solved it for me was understanding that the "mark-to-market" treatment under Section 1256 creates two separate tax events: one on December 31st (the deemed sale) and another when you actually close the position. For your bear put spread, you need to calculate the fair market value of each leg as of December 31st. The long 4800 put and short 4700 put each get treated as if they were sold and immediately repurchased at those values. This creates your 2023 tax liability/benefit under the 60/40 rules. Regarding the tax software issue with negative cost basis - this is definitely a common problem. What worked for me was creating separate entries for each leg rather than trying to enter them as a spread. For the short leg, I entered the premium received as the "proceeds" and the December 31st mark-to-market value as the "cost basis." This gives the correct economic result without triggering the software's validation errors. The IRS instructions are confusing on this point, but the underlying principle is that each Section 1256 contract stands alone for tax purposes, even when they're part of a larger strategy. Don't let the software limitations force you into incorrect reporting - the tax law is what matters, not what the software easily accepts.
Wait, I'm confused about one thing. If you e-filed your amended return, why would TurboTax give you a 1040-V at all? I thought amended returns (Form 1040-X) had to be filed by mail, not electronically. Has this changed recently?
As of 2020, you can e-file amended returns now! It was one of the changes they made during COVID that stuck around. But only certain tax situations qualify for e-filing amendments. If your amendment involves certain schedules or forms, you might still have to paper file.
Just to add some reassurance to what others have said - you're absolutely right to be confused about this! The 1040-V situation is one of those quirks where the tax software doesn't have enough context to know you've already overpaid. I went through something very similar two years ago with a backdoor Roth conversion that got reported incorrectly. Had already paid way more than I owed, filed an amended return, and got that same 1040-V telling me to send more money. I ignored it completely and everything worked out fine - got my refund about 4.5 months later. The key thing to remember is that the IRS systems will reconcile everything when they process your amended return. They can see your original payment and will automatically issue the refund for the overpayment. No need to send additional money or paperwork beyond what you've already e-filed. One tip: keep good records of your original payment confirmation and the acceptance confirmation for your amended return. If there are any delays or questions later, having those documents handy will make resolving issues much easier.
17 Has anyone actually had the IRS contact them over a wrong address on a W2? I've had this happen twice (once my employer put the wrong apt number, once they used my old address) and filed with my correct address both times. Never heard a peep from the IRS about it.
2 I've never heard of anyone having issues with this either. The IRS deals with millions of returns - they're not going to flag something as minor as a house number being wrong when all the important financial info matches up.
I'm a tax preparer and can confirm what others have said - address discrepancies on W-2s are extremely common and won't cause any issues with your tax filing. The IRS uses your SSN as the primary identifier, and the financial data (wages, withholdings) is what matters for processing your return. When you file your 2024 tax return, just use your correct current address. This automatically updates your address of record with the IRS. I've prepared thousands of returns over the years with similar situations and have never seen the IRS flag or delay a return due to a W-2 address mismatch. Your concern about missing correspondence is understandable, but since you'll be filing with your correct address, any future IRS communications will go to the right place. The only time address issues become problematic is if there are discrepancies in the actual tax data (income amounts, withholdings, etc.), which isn't your situation.
Thank you for the professional perspective! It's really reassuring to hear from someone who deals with this regularly. Just to clarify - when you say "automatically updates your address of record," does this happen immediately when the return is filed, or only after it's processed? I'm wondering if there's any timing issue where the IRS might try to send something to the old W-2 address before my return gets fully processed.
Has anyone actually tried exercising and selling in the same tax year to avoid AMT entirely? My financial advisor suggested this approach, but I'm not sure if it works in all situations.
That strategy can work but you lose the potential for LTCG treatment. If you exercise and sell in the same year, the entire gain is treated as ordinary income. So you avoid AMT but potentially pay more in regular tax. It really depends on how much the stock has appreciated and what your regular income is. For my situation with a startup that had 5x growth, it was actually better to take the AMT hit and then get LTCG treatment a year later, even considering the time value of money. Run the numbers both ways!
One thing that really helped me understand this was realizing that AMT creates a "parallel tax system" where you essentially maintain two sets of books. When you exercised your ISOs, you paid AMT on the bargain element, but that payment creates an AMT credit that you can use in future years when your regular tax exceeds your AMT. The key insight is that when you sell after holding for over a year, your AMT basis in the stock is higher than your regular tax basis (because it includes that bargain element you already paid AMT on). This means your AMT gain will be smaller than your regular tax gain, creating what's called a "negative AMT adjustment" that helps you recover the AMT credit. So you're not being taxed twice - you're actually on track to recover some of that AMT you paid through the credit system. Just make sure you file Form 8801 to claim your AMT credit when you sell!
This is such a helpful explanation! I'm new to dealing with stock options and the "parallel tax system" concept really clicked for me. Quick question - do I need to do anything special to track my AMT basis, or does the tax software usually handle that automatically? I want to make sure I don't mess up the Form 8801 when I eventually sell my shares.
Giovanni Gallo
You might want to look into filing Form 8082 (Notice of Inconsistent Treatment) with your return. This lets the IRS know you're reporting something differently than how it was reported to you. Since the 1099 has both names but you're only reporting part of the income, this form can help explain the discrepancy and potentially avoid automatic notices.
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Fatima Al-Mazrouei
ā¢Just be careful with Form 8082 - it basically waves a flag to the IRS saying "look here!" which could increase audit risk. Not saying don't file it, but be extra sure all your documentation is super solid before doing so.
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Demi Lagos
This is a really complex situation that requires careful handling. Based on what you've described, I'd strongly recommend getting professional help from a tax attorney or CPA who specializes in divorce situations, especially since you're dealing with multiple years of unfiled returns. Here's my understanding: Since your name appears on the 1099, you likely have some obligation to report income, even though only your husband's SSN is listed. The IRS could potentially come after you later if they determine you received unreported income. However, the exact amount you should report depends on your actual involvement and benefit from the business. A few key points to consider: - Document everything about your role in the business (emails, texts, bank records showing deposits/expenses) - Determine what percentage of the business operations and income you were actually responsible for - Consider whether you want to file amended returns for those past years or just handle going forward properly Given that you're in divorce proceedings and dealing with $28k annually, the cost of professional tax advice will likely be much less than potential penalties or problems down the road. Don't try to navigate this alone - the stakes are too high and the rules too complex.
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