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Ask the community...

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Luca Ferrari

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One thing nobody has mentioned yet - if you have ANY other Traditional IRA assets with pre-tax money in them (like from old 401k rollovers), the conversion option gets more complicated because of the pro-rata rule. The IRS won't let you just convert the non-deductible portion - you have to convert proportionally across all your Traditional IRA assets. Recharacterization avoids this issue completely since it's like the Traditional contribution never happened. So if you have other Traditional IRA assets, definitely go the recharacterization route while you still can!

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CosmicCadet

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Oh that's really good to know! I actually do have an old 401k that I rolled into a Traditional IRA last year. So if I did conversion instead of recharacterization, I'd have to convert some of that old 401k money too and pay taxes on it?

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Luca Ferrari

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Yes, that's exactly the issue. With the pro-rata rule, you can't cherry-pick which dollars to convert. If you have $9,500 in non-deductible contributions and, say, $40,000 in pre-tax money from your old 401k rollover (all in Traditional IRAs), then any conversion would be proportionally taxable. If you converted $9,500, about 19% would be considered non-taxable (your non-deductible portion) and 81% would be taxable. The IRS looks at all your Traditional IRAs as one big bucket for this calculation. Recharacterization bypasses this completely since it's treated as if you never contributed to the Traditional IRA in the first place.

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Nia Wilson

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Anybody have experience with Fidelity handling these recharacterizations? Their website is confusing me. Do I need to call or can I do it online?

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I did a recharacterization with Fidelity last year. Had to call - couldn't find any way to do it online. The phone rep was actually really helpful and processed it while I was on the call. Had to confirm I understood the tax implications but it was pretty straightforward once I got through to someone.

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NebulaNova

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Hey just wanted to add - I was in a somewhat similar situation with the First Time Homebuyer Credit a few years back. The one thing I learned is that you should stop making those $500 payments ASAP if you have documentation proving your closing date was in 2009. The reason is that continuing to pay acknowledges the debt. Talk to a tax pro, but in my case, I was able to get the IRS to recognize that I had incorrectly categorized my purchase date and should have received the non-repayable credit. I didn't get back what I'd already paid, but I was relieved of future payment obligations. Make sure you keep ALL your closing documents safe - you'll need them if the IRS questions why you stopped making payments.

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Dylan Cooper

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Did you have to file any special forms when you got them to stop requiring repayment? I'm worried if I just stop paying the $500 installments it'll trigger some kind of automatic collection process. Did they give you any pushback or was it fairly straightforward once you showed them the correct closing date?

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NebulaNova

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I had to file a Form 843 (Claim for Refund and Request for Abatement) along with a detailed letter explaining the situation. I attached copies of my closing documents clearly showing the 2009 date, plus copies of my original tax returns where I made the mistake. The IRS did initially send some automated notices when I stopped making the payments. That's why it's important to be proactive rather than just stopping. They eventually processed my claim and sent a letter confirming I was no longer responsible for the remaining payments. It took about 5 months total from submission to resolution.

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Just a quick tax tip that might help others - the First Time Homebuyer Credit had different versions depending on when you purchased: - April 9, 2008 - Dec 31, 2008: $7,500 credit that must be repaid over 15 years - Jan 1, 2009 - Nov 6, 2009: $8,000 credit with NO repayment required - Nov 7, 2009 - April 30, 2010: $8,000 credit for first-time buyers OR $6,500 for long-time residents So the OP definitely got caught in an unfortunate timing situation by accidentally claiming the 2008 credit when their purchase was actually in 2009. Just 3 days difference between a loan and a true credit!

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Paolo Conti

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That's why I always tell people to triple-check dates on major tax credits! The government loves to create these weird cutoff periods that can cost you thousands. I had a client who missed the solar tax credit by ONE DAY because of installation timing. Brutal.

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Ellie Kim

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Something nobody's mentioned yet - make sure you're calculating the $83,500 limit correctly. It includes: - Your pre-tax/Roth 401k contributions (max $23,000 or $30,500 if over 50) - Employer match and any profit sharing - After-tax contributions But if you're self-employed with a Solo 401k or have a SEP IRA, the calculations can be different. Also, the limit is per-employer, so if you changed jobs mid-year, you might actually be ok.

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Fiona Sand

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Wait the $83,500 limit is per employer?? I thought it was a total annual limit across all accounts? Does that mean if I contribute to a 401k at two different employers in the same year I could potentially contribute up to $167,000 total??

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Ellie Kim

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Yes, the $83,500 annual addition limit (for 2024) is technically per-employer. So if you work for two completely unrelated employers who each have their own 401(k) plan, you could potentially contribute up to the limit in each plan. However, your personal elective deferral limit ($23,000 for 2024, or $30,500 if you're over 50) is a combined limit across all employer plans. So while you can't defer more than $23,000 total between both employers' plans, you could still potentially reach the annual addition limit at each employer through employer contributions and after-tax contributions.

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The 1099-R with Code G is only showing your mega backdoor Roth conversion amount, not your total contributions. The Code P you're referring to would only appear if Vanguard had identified and distributed excess deferrals back to you. Check your W-2 Box 12 codes D, AA, and BB to see your actual pre-tax and Roth 401k contributions. Then get your total employer contributions from your year-end statement. Add those three together and if they're over $83,500, THEN you have an excess contribution.

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This is super helpful. What about if some of my money went to ESPP (employee stock purchase plan)? Does that count toward the $83.5k limit? And also do you know if we can just leave excess contributions in there and pay the penalty? Is it just 6% per year or are there other issues?

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CosmicCadet

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Former tax preparer here - another approach if the school won't provide a breakdown: calculate the hourly rate for the whole program, then multiply by the hours that are clearly for childcare (before/after normal school hours and summer). For example: - If you pay $12,000/year for a program that's 8 hours/day (8am-4pm) for 50 weeks - That's 2,000 hours total = $6/hour - If you need extended care from 7am-8am and 4pm-6pm (3 extra hours daily), that's 750 extra hours per year - 750 hours Ɨ $6/hour = $4,500 qualified childcare expense This is a reasonable method that should satisfy the IRS if questioned, since you're using a consistent methodology to separate educational vs childcare costs.

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That's really helpful! I hadn't thought about breaking it down hourly like that. My daughter is there from 7:30am-5:30pm most days, with regular program hours being 9am-3pm, so that's 4 extra hours daily that are clearly for childcare purposes. Summer is about 8 weeks when she's there full-time. Does this sound like a reasonable approach?

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CosmicCadet

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That approach sounds perfect for your situation. With regular program hours of 9am-3pm and your daughter attending 7:30am-5:30pm, you've got 4 hours of extended care each day that clearly qualifies for the credit. For the summer period (8 weeks), you can count all hours as qualified childcare expenses since regular school wouldn't be in session. The IRS recognizes that summer programs serve a dual purpose of education and allowing parents to work, so the full cost during that period typically qualifies regardless of content.

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Chloe Harris

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I just want to add that you should definitely file Form 2441 with your taxes to claim the Child and Dependent Care Credit. The max eligible expenses are $3,000 for one child or $6,000 for two or more children, and the credit percentage depends on your income (ranging from 20-35%). Make sure the Montessori provides their tax ID number (EIN) since you'll need that on the form. Most reputable child care providers are used to providing this info for parents.

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Actually, the Child and Dependent Care Credit maximum was temporarily increased a couple years ago but has reverted back to the lower amounts for 2025 filing. Always check the current year's limits because Congress keeps changing these numbers.

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StarSailor

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One thing nobody has mentioned yet - make sure you establish a health insurance plan reimbursement arrangement through your S corp in WRITING. My accountant said this was critical. We created a simple document that outlines how the S corp will reimburse health insurance premiums for employees (just my wife and me). Without this written plan, the IRS could potentially disallow your deductions during an audit. Also don't forget that the deduction for S corp health insurance is limited to your business income. If your S corp has a loss for the year, you can't deduct the premiums.

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Do you have a template for that written plan? Or did you have your accountant create it? I'm trying to figure out if this is something we can do ourselves or if we need professional help with it.

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StarSailor

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I created it myself based on some research, then had my accountant review it. It doesn't need to be super complex - mine is about 2 pages. It basically states that the corporation will reimburse employees (including shareholder-employees) for health insurance premiums up to a certain amount annually. Key elements to include: effective date, eligible employees, what expenses are covered, maximum reimbursement amounts, how/when reimbursements will be processed, and documentation requirements (employees need to submit proof of premium payments). You should also state that it's intended to comply with relevant tax regulations.

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Marketplace insurance might actually be a good option since you mentioned you left your job recently. You'd qualify for a Special Enrollment Period due to loss of coverage, so you don't have to wait for open enrollment. For our S corp, we found that getting individual marketplace plans and having the company reimburse us worked better than a group plan because we qualified for premium tax credits based on our salary (not including distributions). You do need to be careful about how you structure your salary vs distributions to maximize the benefits.

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Yara Sabbagh

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I did this with my S-corp and it works well, but make sure you understand the income reporting. The marketplace uses MAGI (modified adjusted gross income) to determine subsidies, which includes your W-2 wages plus business profits passed through to your personal return.

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