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Don't overlook the redemption rules with Section 1202! My business acquisition got disqualified because the target company had redeemed shares from a departing founder just 12 months before I invested. The "2-year look-back" rule meant my stock didn't qualify. Make sure there haven't been any redemptions within 2 years before your purchase, and don't plan any redemptions within 2 years after. Also, if you're buying from existing shareholders rather than getting new shares issued directly from the company, that's generally not going to qualify as QSBS.
Thanks for bringing this up - I hadn't even considered redemption timing issues. Is there any exception if the redemption is very small compared to the total outstanding shares? For example, if they bought back 2% of shares from a departing employee?
There is a de minimis exception for redemptions, but it's very limited. The exception only applies if the total value of stock redeemed within the relevant period doesn't exceed $10,000 OR 2% of the value of all outstanding stock at the beginning of the period. So for most businesses of meaningful size, that 2% threshold is really tiny. The safest approach is to ensure no redemptions have occurred in the look-back period. If there have been redemptions, you'll need to carefully analyze whether they fall within the de minimis exception or whether there's a qualifying exception for death, disability, or divorce (there are specific carve-outs for these situations).
Javier Cruz
Has anyone else run into issues with the "active business" requirement? I bought a manufacturing business that qualified initially, but we started generating significant interest income from our cash reserves (about 15% of our income), and our accountant warned this might jeopardize our Section 1202 qualification.
Emma Wilson
ā¢Yes, this is a real concern! One way around this is to establish a separate entity for your excess cash/investments. The "active business" test requires that at least 80% of assets be used in the active conduct of a qualified business. If your cash reserves are getting too large, you could dividend out excess cash to yourself and then invest personally, or create a separate investment entity that wouldn't affect your QSBS-eligible company.
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18 One thing no one has mentioned yet - if you're looking to minimize penalties, you might want to consider applying excess contributions to a future year if possible. I did this for one of my excess contribution years and it saved me from having to withdraw anything.
2 Can you explain how that works? I thought you couldn't "carry forward" Roth contributions like that?
18 You're right that you can't exactly "carry forward" Roth contributions in the traditional sense, but if you're eligible to contribute in the current year, you can apply excess contributions from a prior year to the current year instead of withdrawing them. For example, if you made an excess contribution in 2021, and you're eligible to contribute to a Roth in 2023 but haven't maxed it out yet, you can apply some or all of that 2021 excess amount toward your 2023 contribution limit. You'd still owe the 6% penalty for 2021 and 2022 (if you didn't fix it before the 2022 deadline), but you'd avoid the penalty for 2023 and beyond without having to withdraw funds.
10 Does anyone know if there's a statute of limitations on fixing these excess contributions? I discovered I had the same issue but going back to 2019-2020.
6 I believe the 6% penalty continues indefinitely until you fix the excess contribution, but I'm not sure if there's a point where the IRS won't let you fix it anymore.
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Daniel Price
One thing to consider with HSAs is that the contribution limit and eligibility requirements can be complex if your situation changes. I had a similar situation with a non-calendar year plan, and here's something that bit me: if your health coverage changes mid-year and you lose HSA eligibility, you generally have to prorate your contributions for that year. Make sure your HR department updates your payroll deductions correctly if your plan changes in July. Mine didn't, and I ended up with an excess contribution that I had to withdraw and report on my taxes. It was a mess to fix.
Olivia Evans
ā¢Did you have to pay penalties when you withdrew the excess contribution? I'm in a similar boat and wondering what the damage might be.
Daniel Price
ā¢No penalties as long as I withdrew the excess contribution (plus any earnings on that amount) before I filed my taxes for that year. The earnings were treated as taxable income, but that was minimal in my case. If you've already filed or it's been longer than your tax deadline, there's a 6% excise tax on excess contributions for each year they remain in the account. Don't delay dealing with it - that penalty can add up!
Just a heads up that it's sometimes worth checking if your employer will adjust the plan deductible to maintain HSA eligibility. When the limits changed a few years ago, my company bumped our deductible up by $100 mid-year specifically so employees wouldn't lose HSA eligibility. Might be worth asking your benefits department if they're planning to make any adjustments in July when your plan renews.
Aiden Chen
ā¢This is great advice. Our company did the same thing when the limits changed in 2022. HR sent out a notice that they were adjusting the deductible to maintain HSA eligibility for everyone. They said it was easier than dealing with all the payroll adjustment requests that would happen otherwise.
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You might want to check with the research platform directly about their policy. Some platforms actually consider research participants as independent contractors and will send 1099-NECs, while others might classify payments as "prizes/awards" and issue 1099-MISC forms instead. The $600 threshold applies in both cases, but it's good to know which form to expect. I do psychological studies through three different universities, and each handles it differently!
KhalilStar
ā¢Do you know if there's any way to check their policy beforehand? I've looked through their FAQ but there's nothing specifically about tax forms.
Check the terms and conditions you agreed to when signing up - sometimes tax information is buried there. If you can't find anything, just email their support team directly. They should be able to tell you their policy. Another place to look is in any payment confirmations they send - sometimes there's fine print mentioning tax reporting. If all else fails, you can contact them in December to verify whether they'll be sending a form and where they'll be sending it so you don't miss it.
Don't forget you should be reporting this income regardless of whether you receive a 1099! I learned this the hard way. The research company I worked with didn't send me a form because they claimed I was $25 under the threshold (I thought I'd crossed it). I didn't report the income and got a letter from the IRS a year later - turns out the company DID report it to the IRS even though they didn't send me a form. Had to pay the tax plus a small penalty. Not worth the headache!
How did you end up resolving it? Did you have to file an amended return?
Yuki Yamamoto
Don't forget about state taxes too! The IRS garnishment might be federal, but if you haven't filed federal returns, chances are you haven't filed state returns either. States can be even more aggressive with collections sometimes. Make sure you address both when getting caught up, or you might fix the federal issue only to have the state start garnishing next. Some states have different lookback periods for refunds too, so you might be able to claim refunds from years that are too old for federal.
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Zara Malik
ā¢That's a really good point I hadn't considered. I'm in Texas so I don't have state income tax, but I did live in California for part of 2020 before moving. Does that mean I need to file a partial year California return for that period?
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Yuki Yamamoto
ā¢Yes, you would need to file a part-year resident California return for 2020. California is particularly aggressive with non-filers and has a longer statute of limitations than the IRS for certain things. Since you sold property during that period, California will be especially interested in whether any capital gains tax is due to them. When you file as a part-year resident, you'll only pay California tax on income earned while living there, plus any California-source income (like rental income from California property) earned after you moved. Given the housing market in 2020, there might be significant tax implications depending on how long you owned the California property.
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Carmen Ruiz
Has anyone used TurboTax to file back taxes? I'm in a similar situation (3 years unfiled) but don't know if I should use software or find a professional.
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Andre Lefebvre
ā¢You can use TurboTax for prior years, but you'll need to buy the desktop software for each specific tax year you need to file - the online version only works for current year. And if your situation includes property sales or complex investments, you'll definitely need the premium versions.
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