For anyone using QuickBooks, there's a specific way to handle this. Set up a separate account for sales tax collected, and when you run reports, make sure to exclude that account from your income reports. Then when you pay the tax to the state, it zeros out that account. Your 1099K will still show the full amount, but your accounting will clearly show what was sales tax vs actual income.

This is such a helpful thread! I'm dealing with a similar situation but with Amazon FBA sales. Amazon collected and remitted sales tax on my behalf in multiple states, but my 1099-K shows the gross amount including all that tax. One thing I learned from my CPA is to make sure you have documentation showing which portion of your 1099-K represents sales tax that was remitted by the marketplace vs. sales tax you collected and paid yourself. Amazon provides monthly settlement reports that break this down clearly. Also, if you're using estimated tax payments for next year, remember to base your calculations on your actual taxable income (after deducting the sales tax), not the inflated 1099-K amount. I almost overpaid my Q1 estimated payment because I was using the wrong baseline number!

I see a lot of great advice here about quarterly payments and penalties, but I want to emphasize something crucial that could save you significant stress and money: get professional help NOW rather than trying to figure this out yourself. Estate taxation has so many moving parts - determining what income belongs to the estate vs. beneficiaries, calculating estimated payments correctly, understanding Income in Respect of Decedent rules, choosing between calendar and fiscal years, etc. One mistake can cost thousands in penalties or missed deductions. Since you mentioned the estate has rental properties generating $4,500/month plus investment dividends, you're looking at substantial income that definitely triggers quarterly payment requirements. The fact that you're already past the April 15 deadline means time is of the essence for penalty mitigation strategies. I'd strongly recommend finding a CPA or tax attorney who specializes in estate and trust taxation. Yes, it's an upfront cost, but they can often save you more than their fee through proper planning, penalty abatements, and identifying deductions you'd miss on your own. They can also help you set up systems to handle ongoing quarterly payments properly. Don't let the complexity overwhelm you - this is a common situation and there are professionals who handle it routinely. The key is acting quickly since tax deadlines don't wait for anyone to get up to speed.

I'm dealing with a similar situation after my grandmother passed three months ago, and I wanted to share what I've learned that might help. The estate has been generating income from her rental property and some stock dividends, and I was initially terrified about the quarterly payment requirements. First, don't panic about missing the April deadline - there are several penalty relief options available, especially for first-year estates. I was able to get penalties waived by demonstrating that as a first-time executor, I had reasonable cause for the delay while learning about these requirements. One thing that really helped me was understanding that you have options for calculating the payments. The safe harbor method (paying 100% of current year liability or 100%/110% of prior year) gives you certainty, but if your uncle had little to no tax liability in his final year, the annualized income method might work better given the uneven nature of estate income. Also, make sure you're properly distinguishing between income that belongs to the estate versus income that should be reported by beneficiaries. This was a major source of confusion for me initially. Rental income from properties still held by the estate definitely counts, but the treatment of dividends depends on several factors including when they were declared and paid. I'd strongly suggest getting at least a consultation with a CPA who specializes in estate taxes. Even if you handle some of the legwork yourself, having someone review your approach can prevent costly mistakes. The quarterly payment system continues as long as the estate remains open, so getting it right from the start is crucial.

Am I the only one who just reports these things as income and then deducts them as job search expenses on Schedule A? Since job hunting expenses aren't deductible anymore (thanks Tax Cuts & Jobs Act), I'd probably just pay the tax on it and move on rather than fighting with the company. It's annoying but sometimes the hassle of trying to get a corrected form isn't worth the tax savings, especially if it's not a huge amount. Just my two cents!

I went through this exact same situation two years ago with a Fortune 500 company. The key thing to understand is that this is actually a pretty common mistake companies make - their accounting systems often automatically generate 1099-MISC forms for any payment to non-employees without distinguishing between actual income and expense reimbursements. Here's what worked for me: I called their accounts payable department (not HR) and spoke with someone who actually understood the tax implications. I explained that under IRS guidelines, reimbursements for documented business expenses under an "accountable plan" shouldn't be reported as income. Even though they didn't formally call it an accountable plan, the fact that you provided receipts and they reimbursed actual expenses qualifies. The accounts payable person immediately understood the issue and issued a corrected 1099-MISC within a week. They told me this happens several times a year and they have a standard process for fixing it. If you can't get them to correct it, definitely don't just pay tax on money that was rightfully yours to begin with. The offset method on Schedule 1 that others mentioned is correct, but getting the company to fix their mistake is always the cleaner solution. Don't let them pass their accounting error onto your tax bill!

Small business owner and former bookkeeper here. A simple approach I've used with clients: create "product cost sheets" for each type of item you make. For example, if you make jewelry, figure out the average cost of materials for each earring/necklace/bracelet type. Then just track how many of each product you sell. Multiply sold quantities by your standard costs = COGS. You can put this on Schedule C Part III, and you don't need complex inventory systems. This method is allowed for businesses under the gross receipts thresholds. You should still do occasional checks to make sure your standards are accurate (like once a year), but this saves SO much time compared to tracking every single component.

As someone who's been dealing with this exact issue for my small pottery business, I can share what finally worked for me. The key insight is that you don't need formal inventory tracking, but you do need some reasonable method to estimate what materials went into sold products. Here's my simple approach: I created a basic spreadsheet with standard material costs for each product type (like $3.50 in clay and glazes per mug, $5.25 per bowl, etc.). Then I just track how many of each item I actually sold during the year. At tax time, I multiply quantities sold by standard costs to get my COGS. For your jewelry business with $8,700 in sales, this method would work perfectly. You could estimate something like "each necklace uses $4 in materials, each pair of earrings uses $1.50" based on your typical designs. Then just track your sales quantities - no need to count individual beads! The IRS accepts this simplified approach for small businesses like ours. I do a basic inventory count once a year just to verify my standards are still accurate, but it's way more manageable than tracking every component. This goes in Part III of Schedule C, and it's completely legitimate under the small business accounting methods.

This is a great question that highlights how complex RSU taxation can be! As someone who's navigated similar confusion, I think the key insight from the discussion so far is that wash sale rules only apply to losses, not gains. But here's another angle to consider - even if your sale was at a loss, RSU vests can sometimes avoid triggering wash sales due to the "compensation vs. purchase" distinction that Sean mentioned. The IRS has generally treated RSU vests as compensation events rather than voluntary stock purchases. That said, I've noticed some brokerages are becoming more conservative in their wash sale reporting, especially with company stock transactions. They might flag potential wash sales even in borderline cases to avoid underreporting issues. For future reference, it's worth tracking not just the timing but also the exact share lots and cost basis of your RSU sales versus vests. Sometimes what looks like a wash sale on the surface doesn't actually meet all the technical requirements when you dig into the details.

Great question about fractional shares and brokerage differences! In my experience, the wash sale rule applies based on the number of shares involved, not necessarily requiring exact quantity matches. If you sold 50 shares at a loss and then vest 100 shares within 30 days, the wash sale would typically apply to 50 shares (the lesser amount). For fractional shares specifically, most brokerages will round to determine wash sale applicability, but the exact methodology can vary. Some use a "substantially all" standard where small fractional differences don't prevent wash sale treatment. Regarding brokerage differences - absolutely! I've seen significant variations in how different platforms handle RSU wash sale reporting. Fidelity tends to be more conservative and flags borderline cases, while E*Trade (now Morgan Stanley) sometimes misses cross-account wash sales entirely. Schwab falls somewhere in the middle. My recommendation is definitely to do your own calculations and not rely solely on 1099-B reporting. I keep a spreadsheet tracking all my company stock transactions with dates, quantities, and cost basis. When tax time comes, I compare my analysis to what the brokerage reports and make adjustments on my return if needed. The IRS ultimately cares about the correct tax treatment, not what your brokerage happened to report.