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Just make sure you're keeping really detailed records of all your ESPP transactions!!! I got audited last year because I messed up reporting my ESPP sales and it was a nightmare š© I didn't have proper documentation of my purchase prices and discount amounts for each lot of shares, and had to reconstruct everything from scratch. Now I keep a spreadsheet with every purchase date, offering date, discount amount, purchase price, fair market value, and sale information.
For handling ESPP sales with multiple lots, I've found that FreeTaxUSA actually handles these transactions much better than TurboTax. It has a more intuitive interface for entering the ordinary income portion separately from the capital gains/losses. The key is to make sure you're reporting each lot sale correctly: 1. The discount portion goes on your W-2 as ordinary income (your employer should handle this) 2. The capital gain/loss goes on Schedule D, using the fair market value on purchase date as your cost basis (NOT the discounted price you paid) If you're still having trouble, consider using Form 8949 to provide additional details for each transaction. The IRS wants to see that you understand the difference between the compensation element (discount) and the investment element (capital gain/loss). And definitely keep those detailed records like StormChaser mentioned - having everything documented by lot makes tax time so much easier!
This is really helpful! I've been struggling with understanding the cost basis calculation for ESPP sales. Just to clarify - when you say use the fair market value on purchase date as the cost basis, does that mean I should ignore the discounted price I actually paid? For example, if the fair market value was $100 on purchase date but I paid $85 (15% discount), my cost basis for capital gains purposes would be $100, not $85? And the $15 discount would already be reported as ordinary income on my W-2? I want to make sure I'm not double-counting anything when I report these transactions.
Has anyone used tax software like QuickBooks or TaxAct for this? I have a similar situation with my S-Corp and wondering if the software handles these unrealized losses automatically or if I need to make manual adjustments.
I use QuickBooks for my S-Corp and it handles this pretty well, but you need to set up the accounts correctly. Create an investment account for the stocks, then create a separate unrealized gain/loss account. When you adjust the investment value at year-end, the offset goes to the unrealized gain/loss account. Then when exporting to your tax software, it should identify this as a book-to-tax difference for M-1.
I went through this exact same situation with my S-Corp last year and it was definitely confusing at first. The advice about Schedule M-1 line 5 is spot on - that's exactly where the unrealized loss goes. One thing I'd add is to make sure you document everything clearly in case of an audit. I kept a simple spreadsheet showing the original purchase price ($1,200), year-end fair market value ($550), and the calculation of the unrealized loss ($650). This helps if you ever need to explain the M-1 adjustment. Also, don't forget that when you eventually sell these stocks, you'll need to reverse this M-1 adjustment since the actual gain/loss will be recognized for tax purposes at that point. The unrealized loss adjustment is temporary - it just reconciles the timing difference between book and tax accounting. Your balance sheet approach sounds correct too - showing the securities at fair market value ($550) with the unrealized loss flowing through to reconcile your retained earnings. It all balances out once you get the M-1 schedule right.
This is really helpful documentation advice! I hadn't thought about keeping a detailed spreadsheet for audit purposes. When you mention reversing the M-1 adjustment upon sale, does that happen automatically in most tax software, or do I need to manually track and reverse it? I want to make sure I don't miss this step when I eventually sell these securities.
I work in payroll and deal with this regularly. One thing nobody's mentioned - if the employee had any accrued vacation payout or final wages paid AFTER death, those should be treated differently tax-wise. Those payments go on a 1099-MISC to the estate or beneficiary, not on the W-2. Also, ask for the death certificate copy for your records - you'll need it. In Texas, if they're claiming common law marriage, have them complete a Declaration of Informal Marriage form (it's a Texas state form) if they haven't already filed one with the county clerk.
Do you withhold taxes on the 1099-MISC payments or no? My company had a similar situation and we got conflicting advice.
No, you typically don't withhold taxes on 1099-MISC payments to the estate for final wages paid after death. These payments are considered income to the estate/beneficiary, not wages subject to payroll taxes. The estate will handle the tax obligations when they file the estate tax return or the beneficiary will report it on their personal return depending on how the estate is structured. Just make sure you issue the 1099-MISC by the January 31st deadline and send a copy to the IRS. Always good to double-check with your tax advisor though since estate situations can get complex quickly.
I'm sorry for your loss and the difficult situation you're navigating. This is definitely a complex area that requires careful attention to both federal and Texas state requirements. A few additional points that might help: **Timing considerations:** Since it's already December and the husband is asking about the W-2, you might want to proactively communicate the standard January 31st deadline for W-2 distribution. This can help manage expectations while you're gathering the proper documentation. **Documentation for common law marriage:** In addition to what others mentioned, Texas recognizes common law marriage if three elements are met: (1) they agreed to be married, (2) lived together in Texas as spouses, and (3) represented themselves publicly as married. Evidence could include joint utility bills, insurance policies listing each other as spouses, joint bank accounts, or sworn affidavits from friends/family who knew them as a married couple. **Estate considerations:** Even if you determine they weren't legally married, the W-2 still needs to be issued - it would just go to whoever is handling the estate (could be a parent, sibling, or court-appointed administrator). **Record keeping:** Make sure to document whatever verification process you use for your company's records. This protects you if questions arise later from other family members or during any potential audit. Consider reaching out to your company's legal counsel or tax advisor if you have access to one, especially given the complexity around the marriage status verification.
This is really helpful advice! I'm new to handling payroll situations like this. One question - you mentioned reaching out to legal counsel, but for smaller companies that might not have that resource readily available, are there any specific IRS publications or resources that cover deceased employee situations? I want to make sure I'm not missing any important requirements, especially since this involves both federal tax law and Texas state marriage law. I'd rather over-document than under-document in a situation like this.
Quick question - does anyone know if TurboTax handles this community property LLC situation correctly? I tried entering our business info and it keeps pushing me toward filing two separate Schedule Cs, but after reading this thread, I'm not sure that's right for our Nevada LLC.
TurboTax is terrible with complex LLC situations in my experience. We have a similar situation in Arizona and TurboTax kept getting confused with the community property aspects. We switched to a CPA last year who specialized in small business taxation and discovered we'd been filing incorrectly for years.
Thanks for sharing your experience! That's really helpful to know. I think I'll consult with a tax professional before submitting our return this year. Better to pay a bit more for proper advice than risk doing it wrong and facing problems later.
I've been dealing with this exact same issue for our LLC in California! After reading through all these responses, I think the key takeaway is that the "correct" approach might depend on your specific operating agreement and how you've structured your LLC. What I found helpful was getting clarity on whether both spouses are considered "active participants" in the business. If you're both materially participating, then the self-employment tax treatment becomes more important for Social Security credit purposes. But if one spouse is more of a passive investor, then a single Schedule C under the active spouse's name might make more sense. For your $87,000 income situation, I'd strongly recommend getting a consultation with a tax professional who specializes in small business and community property issues. The cost of professional advice is probably worth it to avoid potential issues down the road, especially since community property state rules can be tricky to navigate correctly. One thing I learned is that the IRS has specific guidance (Rev. Proc. 2002-69) about community property and self-employment tax that might be relevant to your situation. It's worth reviewing if you haven't already!
Thank you for mentioning Rev. Proc. 2002-69! I hadn't come across that specific guidance before. As someone new to this community and dealing with a similar LLC situation in Washington state, I really appreciate all the detailed responses in this thread. One follow-up question - when you mention "material participation" versus "passive investor," is there a specific test or threshold the IRS uses to make this determination? My spouse and I both work in our business, but I handle most of the day-to-day operations while my spouse focuses more on the financial/administrative side. I'm wondering if this difference in roles affects how we should approach the Schedule C filing. Also, has anyone found good resources for understanding how Washington state's community property laws specifically interact with federal tax requirements? I want to make sure I'm not missing any state-specific nuances that might affect our filing approach.
CosmicCruiser
Has anyone run into Zelle transfer limits when doing larger amounts? I tried to move $8k once and my bank limited me to $3500 per day.
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Anastasia Fedorov
ā¢Yeah, it varies by bank. Chase limits me to $2,000 daily and $16,000 monthly for Zelle. For the $15k transfer OP mentioned, they might need to split it up over several days or just do a regular bank-to-bank ACH transfer instead, which usually has higher limits.
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Ellie Simpson
One thing to keep in mind is that while these transfers aren't taxable, you should still keep good records of them. I learned this the hard way when the IRS questioned some large deposits in my account during an audit a few years back. Even though they were just transfers from my other bank, I had to provide documentation proving both accounts were mine and that the money wasn't new income. I'd recommend keeping screenshots of both accounts showing your name, and maybe even a simple spreadsheet tracking the transfer dates and amounts. It's probably overkill, but it'll save you headaches if anyone ever questions where that money came from. The IRS agent told me that clear documentation makes these situations resolve much faster.
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Riya Sharma
ā¢This is really solid advice! I never thought about keeping records for something that seems so straightforward, but you're absolutely right. Better to have the documentation and not need it than to scramble during an audit. Did the IRS give you any guidance on how long to keep those records? I'm assuming it's the same as other tax documents (7 years), but wanted to check since these aren't technically "tax" transactions.
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