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One thing nobody has mentioned yet - the company might have had a reason for issuing a 1099-NEC. Was there any chance this was structured as a buyback with an additional premium? Sometimes companies will pay more than fair market value for shares as a form of severance or additional compensation, especially with early employees. If that's the case, you might need to split the reporting - part as capital gains (the actual FMV of the stock) and part as compensation (any premium above FMV). Worth double-checking your sale documents to confirm the valuation matched pure FMV.
StarStrider
ā¢Thanks for bringing that up. I checked all my documents carefully before posting. The purchase agreement explicitly states the shares were bought at the exact same price as the most recent external financing round - no premium involved. It was a straightforward stock sale at market value, which is why I'm confident it should be capital gains treatment. The company's finance team admitted they "weren't sure how to report it" and went with 1099-NEC because it was "easier for them" than figuring out the broker requirements for a 1099-B. Pretty frustrating when their convenience creates tax complications for former employees.
Just a heads up - I dealt with this exact issue last year with QSBS stock. Make absolutely sure you have documentation proving it qualifies as QSBS! The requirements are strict: - Company must be a qualified small business when you acquired the stock - Must have held the stock for at least 5 years - Company assets must have been under $50 million when stock was issued - Must be original issue stock (bought from company, not secondary) The IRS scrutinizes QSBS claims carefully because of the huge tax advantage. If you're claiming the 50% exclusion, make sure you have rock-solid proof for every QSBS requirement.
Liam Mendez
ā¢I thought QSBS had to be held for at least 5 years to get any exclusion? OP didn't mention how long they held the stock.
You're absolutely right about the 5-year requirement! @f276654cb9eb - this is crucial for your situation. Since you mentioned purchasing the first batch while working there and the second batch after leaving, you need to verify that both batches have been held for at least 5 years to qualify for the QSBS exclusion. If either batch hasn't met the 5-year holding period, you'll still report it as capital gains (not as compensation income from the 1099-NEC), but you won't be able to claim the 50% exclusion on those shares. The holding period starts from when you originally acquired the stock from the company, not when you sold it back. Make sure to track the holding periods separately for each batch since they were acquired at different times. This could significantly impact your tax calculation!
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Has anyone actually tried OLT.com like the OP mentioned? I'm in a similar boat with about $25 in foreign taxes and looking to switch from TurboTax.
Ethan Moore
ā¢I've used OLT for the past two years and it works great for claiming small foreign tax credits directly on Schedule 3. Their interface isn't as slick as TurboTax, but they include all forms in their basic package ($9.95 last time I used it) including Form 1116 if you ever need it.
This is exactly the kind of situation where tax software companies make their money on unnecessary upsells! The $300 threshold rule that others mentioned is spot-on - you absolutely do not need to file Form 1116 for $1.89 in foreign taxes. I've been doing my own taxes for over a decade and have dealt with this same issue multiple times. The IRS specifically created the Schedule 3 direct entry method because they recognized that requiring Form 1116 for tiny amounts was burdensome for taxpayers and created unnecessary complexity. Just to add some additional context: this rule applies to "qualified foreign taxes" which includes taxes withheld on dividends from foreign stocks or international mutual funds/ETFs. Make sure your $1.89 falls into this category (which it almost certainly does based on your description). You can literally save yourself $68 and claim that credit on any free tax software that includes Schedule 3. Don't let TurboTax guilt you into thinking you need their premium version for such a basic tax situation!
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One thing nobody has mentioned yet - if you don't set up a new agreement when your short-term plan expires, the IRS can also offset (take) any future tax refunds until your debt is paid. They do this automatically without having to go through the normal collection process. This happened to me for three years straight before I finally set up a proper installment agreement.
Thanks for mentioning this! Is there any way to protect future refunds once you're in a formal agreement like the PPIA?
Even with a PPIA in place, the IRS will still offset any tax refunds. That's standard for any type of installment agreement. The only way to protect future refunds is to adjust your withholding so you don't have a refund coming - basically aim to break even or owe a tiny amount each year. This actually works in your favor in two ways: you get more money in each paycheck throughout the year (instead of giving the IRS an interest-free loan), and you can use that extra money to make payments on your tax debt, which does reduce interest charges.
KhalilStar
Just want to add that ignoring the end of your payment plan is risky for another reason - the IRS charges both penalties AND interest on unpaid tax debt. The failure-to-pay penalty is 0.5% per month (up to 25% total), and the interest rate is currently around 7%. Those keep accumulating even if they haven't started active collections yet.
Does getting on a PPIA stop these penalties from adding up? My tax debt keeps growing despite making payments.
GalaxyGlider
ā¢Yes, being on a PPIA does reduce the failure-to-pay penalty rate from 0.5% per month down to 0.25% per month, which helps slow down how fast your balance grows. However, the interest will continue to accrue at the full rate on your unpaid balance. The key is that as long as you're making your required PPIA payments on time, you're considered "in compliance" with the IRS, which prevents them from taking collection actions and keeps the penalty rate lower. But unfortunately, there's no way to completely stop interest from accumulating until the debt is fully paid off. @AmieliaDietrich If your debt is still growing despite payments, it might be worth requesting a review of your payment amount through the PPIA process to see if you can qualify for higher monthly payments that actually make progress against the principal balance.
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Has anyone used TurboSelf-Employed for reporting craft sales? I'm trying to decide between that and H&R Block.
I used TurboSelf-Employed last year for my candle business and it was pretty good! Very straightforward with the Schedule C stuff and it walked me through all the possible deductions. It costs more than regular TurboTax though.
@Sophia Long, yes you absolutely need to report that $4,200! Even though it seems like a small amount compared to your regular job, the IRS requires you to report ALL income. Since you made over $400 from self-employment, you'll also owe self-employment taxes (about 15.3% for Social Security and Medicare). Here's what you need to do: 1. File Schedule C to report your business income and expenses 2. File Schedule SE for self-employment tax 3. Start tracking everything NOW - save all receipts for materials, shipping, packaging, even part of your phone/internet bills Don't panic about not having perfect records this year. Try to reconstruct what you can remember spending on supplies, and the IRS is generally reasonable about estimates if they're realistic. One tip: you can deduct the cost of materials, Etsy fees, PayPal fees, packaging supplies, and even a portion of your home if you have a dedicated workspace. These deductions will reduce your taxable income significantly. You've got this! It's not as scary as it seems once you get organized.
Sophia Rodriguez
I'm SO confused by all this tax stuff. My H&R Block software says I need Form 8949 but my friend who uses TurboTax said she didn't have to fill it out at all??? We both have stocks with Fidelity. Does it depend on which tax software you use????
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Mia Green
ā¢Different tax software might present things differently, but the actual IRS requirements are the same regardless of which program you use. Check your 1099-B from Fidelity - if Box 3 is checked for all your transactions (meaning basis was reported to IRS), then technically you don't need to list each transaction on Form 8949. Some tax software might still ask you to enter all transactions individually while others offer a summary option. Either way, the end result should be similar - transactions with reported basis can be summarized on Schedule D instead of being itemized on Form 8949.
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Luca Romano
I went through this exact same situation last year and it was so stressful! The key thing to understand is that when your brokerage reports the cost basis to the IRS (which shows up as Box 3 being checked on your 1099-B), you generally don't need to fill out Form 8949 for those specific transactions. However, I'd recommend double-checking a few things: First, look at ALL your 1099-B forms and make sure Box 3 is checked for every single transaction. If even one transaction has Box 3 unchecked, you'll need Form 8949 for that one. Second, if you had any wash sales or made any adjustments to the cost basis that your brokerage didn't account for, you might still need Form 8949. The Form 8453 your software generated might just be a precautionary measure. Most modern tax software is pretty good about only requiring it when you actually have forms that can't be e-filed. Since you used the summary option and everything was reported by your brokerage, you're probably fine without it. One last tip - keep all your brokerage statements and 1099-B forms for your records, even if you don't need to submit detailed forms. The IRS occasionally sends notices asking for clarification on capital gains, and having those documents makes responding much easier!
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