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Quick question - does anyone know if this NUA strategy still makes sense if you're going to be in a lower tax bracket in retirement? I'm trying to decide between traditional NUA and just rolling everything to an IRA and taking distributions later.
The NUA strategy tends to be most beneficial when: 1. You have significant appreciation in the employer stock 2. The difference between your ordinary income tax rate and capital gains rate is substantial 3. You need access to the funds before typical retirement age If you'll be in a significantly lower tax bracket in retirement, and don't need the funds soon, it might make more sense to roll everything into the IRA. That way you'll pay the lower ordinary income tax rate on distributions in retirement rather than paying some tax now at your current higher rate.
Thanks for breaking that down so clearly. I'm about 10 years from retirement and expect to be in a much lower bracket then. My company stock has appreciated a lot but I don't need the funds anytime soon, so it sounds like maybe the traditional IRA rollover is better in my case. Would love to avoid paying my current high tax rate if I can help it!
This is a great discussion and really helpful for understanding NUA taxation. One thing I'd add for anyone considering this strategy - make sure to understand the timing requirements. You have to take the entire distribution of your employer stock in the same tax year to qualify for NUA treatment. You can't spread it out over multiple years. Also, there's a "lump sum distribution" requirement that means you have to distribute your entire 401k balance within one tax year after a qualifying event (like separation from service). You can't just take out the employer stock and leave other funds in the 401k. The IRS is pretty strict about these requirements, so if you're planning an NUA transaction, work closely with both your 401k provider and tax advisor to make sure you meet all the criteria. Missing any of these requirements means you lose the favorable tax treatment and everything gets taxed as ordinary income.
This is exactly the kind of detail I was missing! I had no idea about the lump sum distribution requirement or that everything had to happen within the same tax year. My 401k provider mentioned NUA as an option but didn't explain all these timing restrictions. So just to make sure I understand - if I want to do NUA with my employer stock, I have to distribute my ENTIRE 401k balance (not just the stock portion) in the same tax year? And I can roll the non-stock portions to an IRA but the stock has to come out to a taxable account to get NUA treatment? This definitely changes my planning timeline. I was thinking I could take my time with this decision, but it sounds like once I trigger a qualifying event, I need to move quickly to meet all the requirements.
Does anyone know if you can bundle these kinds of donations with your regular charitable giving to help hit the itemized deduction threshold? My tax guy isn't very clear on this, and I'm below the standard deduction by about $1000, but I gave almost $2000 to various gofundmes this year.
Unfortunately, you can't bundle non-deductible donations with deductible ones to reach the itemized threshold. Only donations to qualified 501(c)(3) organizations count toward your itemized deductions. Those GoFundMe donations to individuals won't help you reach the threshold at all. If you're close to the standard deduction threshold, you might consider bunching your charitable donations - making two years' worth of planned donations in a single tax year so you can itemize in that year, then taking the standard deduction the next year.
I went through this exact same situation last year and learned the hard way that documentation is everything. Even if you think a GoFundMe might qualify (like when it mentions partnering with a charity), you need official receipts from the actual 501(c)(3) organization to claim any deduction. What I ended up doing was keeping detailed records of all my GoFundMe donations in a separate spreadsheet with notes about why I donated and whether there was any charitable organization involvement. While most weren't deductible, it helped me identify a couple that actually were connected to registered nonprofits - but only after I contacted those organizations directly for proper tax receipts. For future reference, if you want to help individuals while still getting tax benefits, consider looking into donor-advised funds. Some allow you to recommend grants to help specific people in need while still qualifying as charitable deductions since the fund itself is a qualified charity. It's not as direct as GoFundMe, but it's an option for people who want both the personal connection and the tax benefit.
This is really helpful advice about keeping detailed records! I'm curious about the donor-advised funds you mentioned - how exactly do those work for helping specific individuals? Like if I wanted to help that neighbor whose house burned down, could I actually direct the fund to give money specifically to them, or is it more like suggesting they consider cases like theirs? I've never heard of this option before but it sounds like it might solve the problem of wanting to help someone specific while still getting the tax deduction.
Just wondering - have you considered waiting until next year to sell some of the shares? If you hold them in your brokerage account for a year before selling, wouldn't that remove any confusion about the long-term status?
That's not necessary for NUA distributions. The special NUA rules override the normal holding period requirements. The appreciation is treated as long-term capital gain regardless of how long you hold the shares in the brokerage account. This is specifically to allow people to diversify immediately after the distribution without tax penalty. However, any additional appreciation that occurs AFTER the transfer to the brokerage account does follow normal capital gains rules. So if the stock goes up by $10 after the transfer and you sell within a year, that $10 would be taxed as short-term gain, while the original NUA portion still gets the favorable long-term treatment.
Great thread! I'm going through a similar situation with my NUA distribution. One thing I'd add is to make sure your former employer properly coded the distribution on their end too. I found out the hard way that if the 401k administrator doesn't mark it correctly as an "NUA-eligible distribution," it can create problems downstream even if you do everything else right. The distribution needs to be part of a "qualifying event" (like retirement or separation from service) and needs to be a lump-sum distribution of your entire account balance within one tax year. Also, double-check that you didn't accidentally have any company stock in a Roth 401k portion - those shares don't qualify for NUA treatment and need to be handled differently. The rules are pretty strict about what qualifies, so it's worth confirming all the boxes are checked before you start selling shares. The good news is once it's done correctly, you'll have a lot more flexibility in managing your tax burden when you do decide to sell!
This is really helpful info about the qualifying event requirements! I didn't realize the Roth 401k portion couldn't use NUA treatment. That could have been a costly mistake. One question - when you say "lump-sum distribution of your entire account balance," does that mean I need to empty out ALL my 401k accounts with that employer in the same year? I have both traditional and Roth portions, plus I think there might be some after-tax contributions in there too. Do all of those need to be distributed together for the NUA to work properly? I'm worried I might have messed something up since I only moved the company stock portion so far.
Did anyone mention that you CAN actually "pay yourself" for labor on a business vehicle if you have the right structure? I'm a mechanic with an S-corp and I've been paying myself as an employee to work on company vehicles. Company pays me, company deducts it as an expense, I report income on my personal return. My accountant confirmed this is legit if done properly with proper documentation and reasonable rates. You need the right business structure though.
Great question! As someone who's dealt with similar situations in my own small business, I can confirm what others have said - you unfortunately can't deduct your own labor costs even when working on business vehicles. The IRS is pretty strict about this because no actual cash expense occurred. However, don't overlook some other potential deductions that might apply to your situation: - If you have a dedicated workspace at home for your business (even just for paperwork, ordering parts, etc.), you might qualify for the home office deduction - Tools and equipment used for the repairs can be deducted or depreciated - Any training or certification costs to maintain your mechanic skills - Professional subscriptions, trade publications, or software related to your work Also, keep detailed records of everything! Even though you can't deduct the labor, having documentation of the work you performed, time spent, and fair market value could be helpful if you ever get audited - it shows you're running a legitimate business operation. The $3,200 in parts is definitely deductible as you mentioned, and that's still a significant write-off. Sometimes focusing on what we CAN deduct rather than what we can't helps put things in perspective.
This is really helpful advice! I hadn't thought about the home office deduction angle. I do use part of my garage as an office space for invoicing, ordering parts online, and storing business records. Do you know if the space needs to be used EXCLUSIVELY for business, or can it be a mixed-use area? My garage is where I park my personal car too, but I have a dedicated desk area and filing cabinet just for business stuff. Also, regarding the tool deduction - does this apply to tools I already owned before starting the LLC, or only new purchases? I've been using the same toolbox and equipment for years, some from when I worked at other shops.
Eli Butler
Just to clarify something that might help others - there's actually been some changes to the Child Tax Credit over the years that can cause confusion. For 2024 tax year (filing in 2025), the credit is $2,000 per qualifying child under 17, with up to $1,700 being refundable through the Additional Child Tax Credit. The key point everyone's made is correct - no minimum income required for the Child Tax Credit itself. But if you have very low or no income, you'll mainly benefit from the refundable portion (up to $1,700 per child). The non-refundable portion can only offset actual tax liability. Make sure your children have valid Social Security Numbers (not ITINs) to qualify for the full credit. Also, with your income under $10,000, you should definitely file a return even if not required to - that's the only way to get the refundable portion back as a refund.
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Yuki Sato
ā¢This is really helpful clarification! I was actually getting confused by some outdated information online that mentioned different refundable amounts. Quick follow-up question - you mentioned needing valid SSNs vs ITINs. What happens if a child has an ITIN instead? Do you get any credit at all or just a reduced amount?
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NeonNomad
ā¢If a child has an ITIN instead of a valid SSN, unfortunately they don't qualify for the Child Tax Credit at all - you'd get $0 for that child. However, you may still be able to claim the Credit for Other Dependents, which is $500 per qualifying dependent with an ITIN. It's not as generous as the Child Tax Credit, but it's something. The SSN requirement is pretty strict for the Child Tax Credit - it was implemented to prevent fraud and ensure the credit only goes to children who are authorized to work in the US when they reach working age.
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Zara Malik
I want to add something that might help clarify the confusion you're experiencing. The Child Tax Credit has NO minimum income requirement - you can have $0 in income and still qualify. What you might be thinking of is the Earned Income Tax Credit (EITC), which does require earned income. However, here's the important part for your situation with under $10,000 income: while you can qualify for the Child Tax Credit, the benefit you actually receive depends on whether it's refundable or non-refundable. For 2024 (filing in 2025), up to $1,700 per child is refundable through the Additional Child Tax Credit - meaning you can get this as a refund even with no tax liability. The key requirements for your kids (ages 4 and 7) are that they: - Have valid Social Security Numbers (not ITINs) - Lived with you for more than half the year - Are under 17 at the end of the tax year - You provided more than half their support You should definitely file a return to claim this credit, even if your income is below the filing threshold. With two qualifying children, you could potentially get up to $3,400 back as a refund ($1,700 Ć 2) regardless of your low income level.
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Zachary Hughes
ā¢This is exactly the clear breakdown I was looking for! Thank you for explaining the difference between the Child Tax Credit and EITC - I think that's where a lot of my confusion was coming from. The $1,700 refundable portion per child is definitely significant for my situation. Just to confirm I understand correctly - even with my income being under $10,000, I could potentially get $3,400 back ($1,700 x 2 kids) as long as they have valid SSNs and meet those other requirements you listed? That would be a huge help for my family.
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Sean O'Connor
ā¢Yes, that's exactly right! With two qualifying children and income under $10,000, you could potentially receive up to $3,400 back as a refund through the Additional Child Tax Credit portion ($1,700 per child). This is completely separate from your tax liability - it's a true refund even if you owe $0 in taxes. Just make sure both kids have valid Social Security Numbers (not ITINs) and meet those residency/support tests. Given your health issues limiting work this year, you'll definitely want to file a return to claim this - it could make a real difference for your family's finances. One tip: if you use tax software or go to a tax preparer, make sure they don't miss claiming the Additional Child Tax Credit. Some people only focus on the regular Child Tax Credit and miss out on the refundable portion.
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