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11 One thing to watch out for with multiple W-2s: you might end up owing taxes even if each individual employer withheld the correct amount! This happened to me. Basically, each employer calculates withholding as if they're your only job, so they each withhold at a lower tax bracket rate. But when you combine all your income, you might jump into a higher tax bracket. The software will calculate this, but just be prepared that you might not get the refund you're expecting.
23 Omg this just happened to me! I worked 3 jobs last year and ended up owing $600 when I usually get a refund. I was so confused until the tax preparer explained this exact thing.
11 Yeah, it can be a really unpleasant surprise! One way to avoid this in future years is to fill out a new W-4 form at your current job and check the box for multiple jobs, or even request additional withholding. It's better to get a little less in each paycheck than to get hit with a big tax bill in April. It's one of those weird tax things nobody tells you about until you learn the hard way!
4 If you just have W-2s and no other complicated stuff, the IRS actually has a completely free filing option called Free File Fillable Forms. It's very basic but it works! Saved me from paying for TurboTax last year.
8 I tried using that last year and it was so confusing! No explanations of anything, and it doesn't do any calculations for you. Maybe it's fine if you know exactly what you're doing, but for beginners I really wouldn't recommend it.
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Ava Kim
One thing nobody mentioned - if you're eligible for a Traditional IRA contribution for 2022, you could recharacterize the Roth contribution as Traditional instead of taking it out completely. That way you don't lose the tax-advantaged space. You'd still need Form 5329 and an amended return, but no 6% penalty if you recharacterize properly. Just a thought!
Is there a time limit on recharacterization though? I thought the deadline was the tax filing deadline plus extensions for the year of the contribution (so for 2022 contributions, it would have been Oct 2023 at the latest).
Ava Kim
ā¢You're absolutely right about the recharacterization deadline. The deadline is the tax filing deadline including extensions for the year the contribution was made. For 2022 contributions, that would have been October 16, 2023 (if an extension was filed). Since that deadline has passed for 2022 contributions, recharacterization is no longer an option in this case. At this point, the only options are to remove the excess contribution (plus earnings) or apply it to a future year if eligible. This is why catching these issues early is so important - it provides more flexibility in how to correct them.
Layla Mendes
Wouldn't it be easier to just apply the excess contribution to 2023 if you're eligible to contribute to a Roth IRA in 2023? You'd still owe the 6% penalty for 2022, but it would stop there. That's what I did when I had an excess contribution a couple years ago.
That's actually a smart approach if they're eligible for 2023! Would they need to specifically notify their IRA custodian about carrying forward the contribution, or just report it that way on their tax forms?
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Olivia Evans
Something you might consider - what about buying the truck in December, but doing a sale-leaseback arrangement with a third party until January? That way you secure the vehicle now but technically it's not "placed in service" for your business until 2024. I'm not a tax professional, but I did something similar with some expensive manufacturing equipment a few years ago. Might be worth asking your accountant about.
Wouldn't that be considered a step transaction by the IRS though? From what I understand they look at the substance of transactions rather than just the form.
Olivia Evans
ā¢That's a valid concern about step transactions. The IRS can indeed look at the substance over form if they believe transactions were structured solely to avoid taxes. The key difference in what I suggested is that there would be a genuine business purpose - securing a specific needed asset that might not be available later. A properly structured lease with market terms that transfers actual usage rights to another party temporarily could potentially work. But you're right that it would need to be a legitimate arrangement and not just paperwork to achieve a tax outcome.
Aiden Chen
Have you considered just taking the Section 179 in 2023 but carrying forward any unused deduction amount to 2024? If your 2023 income is too low to fully utilize the deduction, the unused portion can be carried forward to future tax years. This is often overlooked but might solve your problem.
Zoey Bianchi
ā¢This is the correct answer right here - I don't know why no one else mentioned it! Section 179 deductions that exceed your business income can be carried forward indefinitely. So if your 2023 business income is too low to fully use the deduction, you can use the remaining amount in 2024.
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Another option nobody's mentioned yet - check your online account at SSA.gov. You can create an account on the Social Security Administration website and view your reported wages, which will show all W-2 income reported under your SSN. Might not have all the withholding details you need, but at least you can verify the income amounts from all your employers.
Will the SSA site show my current year W-2 info though? I thought it only updates annually and wouldn't have my 2024 information available yet for filing in 2025?
You're right to question this - the SSA website typically doesn't show current tax year information in time for filing. It usually updates around July for the previous year's wages. So while it's a good resource for verifying past years or checking if old employers reported your wages correctly, it won't help with your current filing situation. For current year W-2s that you're missing, you'll need to contact either the employer directly or the IRS as others have suggested. The IRS typically has the current year information in their system before it appears in the SSA database.
NeonNomad
I once forgot to include a W-2 for about $2,500 and got a letter from the IRS about 8 months later. They adjusted my return automatically, charged me the additional tax plus interest, and reduced my refund for the following year. Wasn't a huge deal but definitely would have been simpler to just include it from the start.
Did they charge you any penalties or just the tax and interest? I'm in a similar situation but it's been 2 years and I haven't heard anything...
Chloe Davis
Regarding your RSU situation - one strategy my wife and I use is to set up a Donor Advised Fund. Since we're also in a high tax bracket with significant RSU income, we donate appreciated shares directly to our DAF instead of cash. This gives us a double tax benefit: a deduction for the full fair market value of the shares and we avoid capital gains tax on the appreciation. You can fund it in high-income years (like when large RSU blocks vest) to bunch your deductions, then distribute the actual charitable gifts over time. This has been more impactful for our tax situation than the backdoor Roth, though we do that too.
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Natasha Orlova
ā¢This sounds promising! How much paperwork/maintenance is involved with a DAF? And can you recommend any specific providers? I've heard of Fidelity and Schwab having these, but not sure if there are advantages to one over another.
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Chloe Davis
ā¢The paperwork is minimal - much easier than setting up a private foundation. It takes about 15-20 minutes to open online, similar to opening a brokerage account. Once it's set up, you just transfer assets in and then make grants to charities whenever you want with a few clicks. I use Fidelity Charitable because that's where my other accounts are, but Schwab and Vanguard are also excellent options. They all have similar fee structures (around 0.6% administrative fee annually plus underlying investment fees). The main difference is minimum initial contribution ($5K for Fidelity, $5K for Schwab, $25K for Vanguard) and minimum grant amounts. I'd go with whoever you already have investment accounts with for simplicity.
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AstroAlpha
Don't forget to check if your spouse's employer offers a mega backdoor Roth option in their 401k plan. This would allow for additional after-tax contributions beyond the standard 401k limit (potentially up to $46,000 more depending on employer plan specifics and other contributions). Those after-tax contributions can then be converted to Roth money. Not all employers offer this, but it's worth checking if they do since your income is high enough to take advantage of it. Would give you much more tax-advantaged space than just the regular backdoor Roth IRA.
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Diego Chavez
ā¢Just a quick note on this - the mega backdoor Roth requires specific plan provisions: 1) allowing after-tax contributions (not just Roth), and 2) either in-plan Roth conversions or non-hardship in-service distributions. Many plans don't have both features, especially the second one. Worth calling the 401k administrator to check though!
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