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Ask the community...

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Omar Zaki

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Anyone else notice the IRS rules for retirement accounts seem designed to be confusing? Some random thoughts that might help: 1) if u have a 401k at work, the ira deduction phases out at high incomes 2) if ur over the limits, backdoor roth is usually better than non-deductible trad ira 3) dont forget u can do both 401k AND ira in same year, just might not get trad ira deduction 4) also check if ur 401k has after-tax contributions with in-plan roth conversions... thats the "mega backdoor roth" and is awesome if available!!

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Oliver Weber

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Thanks for the tips! I'm going to check if my 401(k) plan allows after-tax contributions with in-plan conversions. That mega backdoor Roth option sounds interesting. And yeah, it does feel like these rules are intentionally complicated sometimes!

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Great question! I was in a similar situation last year and learned this the hard way. Since you're covered by a 401(k) at work and earning $210k, you won't be able to deduct traditional IRA contributions at all - the deduction phases out completely for single filers around $90k and married filing jointly around $136k when you have workplace retirement coverage. Your strategy of splitting $17k traditional 401(k) + $7k traditional IRA wouldn't give you the full $24k in deductions you're hoping for. The $7k IRA contribution would be non-deductible. Instead, consider these options: 1) Max out traditional 401(k) at $24k for full deduction 2) Split between traditional and Roth 401(k) for tax diversification 3) Do backdoor Roth IRA with that extra $7k (but watch out for pro-rata rule with your existing rollover IRA) The backdoor Roth might be tricky since you mentioned having a rollover IRA. You'd either need to roll that into your current 401(k) first (if allowed) or deal with pro-rata taxation on the conversion. Definitely worth running the numbers on different scenarios to see what works best for your situation!

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Hugo Kass

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This is really helpful! I'm new to this community and dealing with a similar situation. Quick question - when you mention rolling the existing rollover IRA into the current 401(k) to avoid the pro-rata rule, how do you know if your 401(k) plan allows that? Is that something I'd need to ask HR about, or is there a way to check the plan documents myself? I have about $45k in a rollover IRA from my previous job and want to make sure I understand all my options before making any moves.

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Yara Khalil

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Actually, the IRS absolutely does care about correct employer attribution! šŸ˜‚ Their matching system isn't just checking total income - it's verifying each specific W-2 against what employers reported. Think of it like your credit report - having the right total but wrong accounts would still be a problem. The good news is that since the total income is correct, this is a relatively simple amendment. Your preparer should file Form 1040-X showing the correct employer for each income amount. Since this doesn't change your tax liability, it's more of an administrative correction than a substantive one.

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Keisha Brown

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I believe it's worth noting that while this does require correction, the IRS may simply send a notice about the discrepancy rather than immediately demanding an amended return. If you receive such a notice, you should respond promptly with an explanation and supporting documentation. However, proactively filing an amendment is generally the safer approach to avoid potential complications down the line.

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Dylan Wright

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I completely understand your concern, especially with this being your first tax season filing separately after your divorce. The employer mismatch absolutely needs to be corrected - the IRS matching system will flag this even though your total income is accurate. Here's what you should do: Contact your tax preparer immediately and request they file Form 1040-X at no cost to you (since this was their error). Make sure to bring both W-2s and clearly show which income should be attributed to which employer. The amendment process typically takes 16-20 weeks, but since you're not changing your tax liability, there shouldn't be any penalties. Given your post-divorce situation, having accurate employer documentation is especially important for any potential support calculations or financial verifications you might need later. Don't let this stress you out too much - it's a common preparer error that's easily fixable!

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One thing nobody's mentioned yet - the timing might matter here too. Were these Incentive Stock Options (ISOs) or Non-qualified Stock Options (NSOs)? Because if they were ISOs and you didn't hold them long enough after exercise (at least 1 year from exercise and 2 years from grant), they get disqualified and treated as NSOs which changes the tax treatment.

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Nia Johnson

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They were NSOs from the beginning. The company was pretty clear about that in all the grant paperwork. Does that change how I should be handling this situation with the potential double taxation?

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For NSOs, it's straightforward then. When you exercised, the spread between strike price and fair market value ($53 - $16 = $37 per share) was correctly reported as ordinary income on your W-2. Your cost basis for the shares is the full $53/share (strike price + spread already taxed). When you sold, you should only be taxed on any gains above $53/share. If you sold for less than $53/share, you should actually have a capital loss to report. Check your 1099-B from Schwab. Many brokers don't correctly report the cost basis for option exercises, especially if you transferred the shares from an employee plan. If the 1099-B shows a lower cost basis than $53/share, you need to make that adjustment on your Schedule D when you file.

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I've seen this happen a lot with my clients. Most tax software lets you make this adjustment pretty easily. Which tax program are you using to file?

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Not OP but I use TurboTax and have a similar issue with my ESPP shares. Is there a specific form or screen where I should be making these adjustments?

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In TurboTax, when you enter your stock sales, look for the section where it asks about "basis adjustments" or "additional information about this sale." For ESPP shares, you'll need to adjust the cost basis to include the discount that was already reported as income on your W-2. TurboTax usually has a specific interview flow for employee stock plans - make sure to select "Employee Stock Purchase Plan" when it asks about the type of stock sale. The software should then prompt you for the purchase price, fair market value at purchase, and any discount already taxed. This prevents the double taxation issue that the original poster is dealing with.

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Liam Mendez

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Everyone's talking about refunds, but the real question is: could you have paid less in total taxes? Look into maximizing pre-tax contributions next year. You only put $2500 in your 401k, but the limit is $22,500 for 2023 and $23,000 for 2024. Even increasing to 10% of your salary would make a big difference in your tax bill. Also consider an HSA if you have an eligible health plan - that's another pre-tax contribution that reduces your taxable income. Between those two things, you could potentially reduce your taxable income by $10k+ and save thousands in taxes.

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This is a really common misconception! The key thing to understand is that your refund amount doesn't reflect how much you paid in taxes - it only shows how much you overpaid during the year through withholding. Breaking down your situation: out of that ~$20k deducted from your paycheck, about $13,800 went to taxes that aren't refundable (Social Security $4,100 + Medicare $1,000 + actual federal income tax liability of ~$6,550 + state taxes of ~$2,000 + $150 you still owe). The remaining $6,200 was federal withholding that exceeded what you actually owed, hence your $1,150 refund. Your effective tax rate is actually quite reasonable for your income level. The "problem" isn't that you're being overtaxed - it's that your withholding was fairly accurate to your actual tax liability, which is actually a good thing! Getting a huge refund means you gave the government an interest-free loan all year. If you want more money in your pocket, consider increasing your 401k contribution (you're only doing $2,500 of the $23,000 limit) rather than trying to get a bigger refund.

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This breakdown is incredibly helpful! I never realized that such a large portion of what's taken from my paycheck (the FICA taxes) isn't even part of the refund calculation. So when I see $20k deducted, I'm mentally including $5,100 that was never going to come back anyway. Your point about increasing 401k contributions makes a lot of sense. If I bumped it up to even 10% of my salary ($6,500), that would save me about $1,430 in federal taxes alone (22% bracket). Plus I'd be building retirement savings instead of giving the government a free loan. Thanks for reframing this - I was focused on the wrong number entirely!

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Omar Fawaz

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Has anyone looked into whether it's better to take distributions from your S-Corp and then fund a backdoor Roth vs setting up these more complex retirement plans? Especially if you expect to be in a higher tax bracket in retirement?

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Chloe Martin

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Distributions vs retirement plans isn't really an either/or situation. Distributions from your S-Corp don't reduce your tax burden now - you still pay personal income tax on S-Corp profits regardless of whether you take distributions or not. The retirement plans discussed here actually reduce your current tax burden while still allowing your money to grow. For example, employer contributions from your S-Corp to a Solo 401k are deductible business expenses, reducing both your taxable business income and self-employment taxes. The backdoor Roth has its place, but it's limited to $7,000 per year (2024) and doesn't provide current-year tax benefits. Most people in your situation would typically do BOTH - max out all available retirement options AND do backdoor Roth if they're over the income limits for direct contributions.

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Zoe Stavros

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This thread has been incredibly helpful! I'm in a similar situation but with one additional wrinkle - I'm also contributing to a HSA through my W-2 job. Does that impact any of the S-Corp retirement plan contribution limits mentioned here? Also, for those who mentioned taxr.ai - did their analysis include HSA optimization as part of the overall retirement planning strategy? I'm trying to figure out if I should prioritize maxing my HSA first before setting up the Solo 401k, or if they work completely independently of each other. One more question - if I set up a Solo 401k through my S-Corp this year, can I still make catch-up contributions when I turn 50 next year, or do those limits get complicated when you have multiple 401k accounts?

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Lara Woods

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Great questions! HSA contributions don't impact your 401k contribution limits at all - they're completely separate. HSAs have their own annual limits ($4,300 for individual, $8,550 for family coverage in 2024) and are actually the most tax-advantaged account available since contributions are deductible, growth is tax-free, AND withdrawals for qualified medical expenses are tax-free. Regarding prioritization, most financial experts recommend maxing HSA first if you have access to one, then employer match, then other retirement accounts. HSAs are essentially a "triple tax advantage" account. For catch-up contributions at 50, you'll be able to make an additional $7,500 in employee contributions across all your 401k plans combined (so still the same $30,500 total employee contribution limit in 2025), but the employer contribution limits from your S-Corp remain the same. The catch-up only applies to employee deferrals, not employer contributions. I haven't used taxr.ai myself, but comprehensive tax planning should definitely include HSA optimization as part of the overall strategy since it's such a powerful retirement savings vehicle, especially if you can afford to pay medical expenses out of pocket and let the HSA grow.

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