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Just to add another dimension to this - have you considered adjusting your 403(b) contributions? Increasing your pre-tax retirement contributions would lower your taxable income. If you can afford to contribute more, it's a win-win - less tax liability now plus more retirement savings. For example, if you contributed an additional $3k to your 403(b), that might reduce your tax bill by $660 or so (assuming 22% tax bracket). Worth considering if you're not already maxing it out!

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That's a really good point I hadn't thought about. Do you know what the max contribution is for 403(b) plans in 2025? I'm definitely not anywhere close to maxing it out - I'm only putting in about 5% of my salary now.

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The contribution limit for 403(b) plans in 2025 is $23,000 for individuals under 50. If you're 50 or older, you can make an additional catch-up contribution of $7,500, bringing your total potential contribution to $30,500. At your current contribution level of about $2,700 (based on your post), you have plenty of room to increase contributions if your budget allows. Even bumping up to 8% or 10% could significantly reduce your tax bill while building your retirement savings. Some employers also offer matching contributions up to a certain percentage, which would be free money if you're not currently taking full advantage of it.

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Nia Harris

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Something no one mentioned yet - have you checked if all 3 employers are withholding Social Security correctly? There's a cap on Social Security tax ($168,600 for 2025), but with multiple employers, each one doesn't know what the others are withholding. If your total income is under the cap this probably isn't relevant, but it's something to check if your wages get higher in future years.

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I think their total income was only like $75k so they're nowhere near the Social Security cap. But that's a good point for higher earners with multiple jobs.

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Tax Preparer charged $390 for service but completely missed the Roth IRA married filing separately limitation

I've been married for seven years and we've always filed our taxes separately. We also put aside money each year to max out our Roth IRA contributions. In January, thanks to trying TaxSlayer for the first time, I discovered something shocking - if you're married filing separately, you can't contribute to a Roth IRA if you make more than $10,000 annually. In all these years of being married, between my previous accountant, TurboTax's premium service, and TaxSlayer, only the latter ever flagged this issue. For seven years, we filed separately and thought everything was fine - no one ever mentioned this limitation. In February 2025, my employer's W2 portal had a security breach that lasted nearly a month, forcing me to file for an extension until October. During this time, we researched how to handle the Roth IRA issue and decided to consult with a professional in person. In September, we visited a Jackson Hewitt office to get my 2024 taxes filed and discuss amending previous returns to "married filing jointly." The preparer, Dave, seemed knowledgeable about our situation and appeared confident he could help. We scheduled a follow-up appointment to resolve everything. When we returned with our documentation and explained the Roth IRA contribution issue, we realized Dave didn't understand the rule about Roth IRA contribution limits for married filing separately. A few days later, he emailed saying amendments "wouldn't be beneficial" and completely missed the point about why we needed to amend. Since the October deadline was approaching and he had all our documents, I reluctantly had him complete just my 2024 return. Yesterday, I went in to finalize everything. During the review, Dave forgot I had worked three days in Colorado in 2024, which resulted in an additional W2 and state tax obligation. I had to remind him because I wanted to ensure I wasn't missing any obligations. When it came time to pay, he said they were charging $390. I don't make a huge income, but because of various 1099s and W2s from investments and side work, that's what they charged. I explained that when I used TurboTax with professional review the previous years, it cost around $135 each time. His response was "well this time you had an expert prepare everything for you." Since it's October 12th, I just paid the $390 for something I probably could've done myself for $135. I ended up with a refund of $140, owing $210 in state taxes, and being charged $390 for the service... and Dave still didn't address the original Roth IRA issue. I'm frustrated and still worried about the potential problems with those previous years' contributions.

Paolo Romano

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In my experience as someone who's worked in tax prep before, I can tell you that many tax preparers at the chain locations are seasonal employees who've taken a basic tax course. They're trained to handle common scenarios but often miss specialized rules like the married filing separately Roth IRA limitation. If you're dealing with something like retirement account contribution issues, you really need either a CPA or an Enrolled Agent who specializes in that area. The difference in knowledge and expertise is huge. For fixing your previous years, I'd recommend: 1) Determine which tax years you need to address (generally the last 3 years can be amended) 2) Calculate the excess contributions for each year 3) Contact your IRA custodian about removing excess contributions 4) File Form 5329 for each year to report the excess contributions 5) Consider whether filing amended returns to change from MFS to MFJ makes sense

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This is really helpful, thank you! Do you think it's better to amend the returns to married filing jointly or just remove the excess contributions? We've been filing separately because my spouse has an income-based student loan repayment plan, so filing jointly would increase those payments. But maybe the Roth IRA penalties would be worse?

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Paolo Romano

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Whether to amend to MFJ or remove excess contributions depends on your complete financial picture. You need to calculate both scenarios to see which costs less overall. For the student loan consideration, calculate how much the income-based payments would increase if filing jointly versus the cost of Roth IRA penalties (6% per year on excess contributions) plus any potential tax benefits lost by filing separately. Sometimes it's cheaper to pay higher student loan payments for a year than pay IRS penalties and miss out on tax credits only available to joint filers. This is definitely a situation where running the numbers both ways is essential before deciding.

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Amina Diop

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Has anyone actually received a penalty notice from the IRS specifically for excess Roth contributions while married filing separately? I've been doing this for 3 years not knowing about the limit, and now I'm worried but haven't received any notices.

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Yes, I got hit with this exact situation last year. The IRS sent me a CP2000 notice about unreported income, and during that review, they flagged my Roth contributions while I was MFS with income over $10k. Ended up with penalties for 3 years of contributions plus interest. It was a mess to clean up, so I recommend being proactive before they find it.

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Diego Mendoza

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Don't forget to also deduct the closing costs from your recent sale too! You mentioned you had costs associated with the sale - those reduce your selling price when calculating gain. So your calculation should be: (Sale price - selling costs) - (Purchase price + purchase closing costs) = Capital gain For example, if you sold for $30k but had $6k in selling costs, your amount realized is $24k. If you bought for $10k plus $4k in buying costs, your basis is $14k. So your gain would be $24k - $14

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Javier Garcia

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Thanks for breaking it down like that! So would real estate commissions count as selling costs? And do I need specific documentation for all this or can I just put the numbers in when I file?

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Diego Mendoza

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Yes, real estate commissions definitely count as selling costs! They're usually one of the biggest deductions from your sale proceeds. Other selling costs that reduce your amount realized include legal fees, transfer taxes, and any seller-paid closing costs. Documentation is important. You should keep your closing statements from both the purchase and sale (HUD-1 forms or Closing Disclosures), plus receipts for any improvements you made to the property. You don't submit these with your tax return, but you'll need them if you're ever audited. When you file, you'll report this on Schedule D and possibly Form 8949, depending on your situation.

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What tax form do you use to report land sale? I sold some acres last year and my tax software confused me.

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Emma Taylor

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You'll report it on Schedule D (Capital Gains and Losses) and possibly Form 8949 (Sales and Other Dispositions of Capital Assets) depending on your situation. Most tax software will guide you through this when you indicate you sold land or real estate. The important thing is to have your purchase information (date, cost, closing costs) and your sale information (date, proceeds, selling expenses) ready.

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Ian Armstrong

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22 A lot of insurance agents don't fully understand the tax implications of their products. When I surrendered my policy, the agent told me "you might have to pay taxes on it" but couldn't explain how much would be taxable. Quick rule of thumb: you pay taxes on (what you get) minus (what you put in). The insurance company should send you a 1099-R form that will show the taxable amount, but it's good to understand how it's calculated so you can verify it's correct. Sometimes insurance companies make mistakes too.

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Ian Armstrong

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10 Is there any way to reduce the tax hit? I'm thinking about surrendering a policy but worried about having to pay a lot in taxes. Can I roll it over into something else tax-free?

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Ian Armstrong

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22 Yes, you have a couple options to potentially reduce or defer the tax impact. If your policy qualifies, you could do what's called a 1035 exchange into an annuity or another life insurance policy. This allows you to transfer the cash value without triggering immediate taxation. Another option is to see if your policy allows for partial surrenders over multiple tax years instead of taking all the money at once. This can spread the tax liability across different years and potentially keep you in a lower tax bracket. Just be aware that each partial surrender can affect your overall basis calculation in complex ways.

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Ian Armstrong

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15 Has anyone ever dealt with surrender fees when cancelling a whole life policy? I'm in a similar situation but my policy shows I'll lose about 12% of the value to surrender charges. Wondering if those fees are tax deductible since they reduce what I actually receive.

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Ian Armstrong

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9 Unfortunately, surrender fees typically aren't tax deductible. They're just considered a reduction in your proceeds. So if your surrender value is $5,000 but you only get $4,400 after surrender charges, you'll only pay taxes on the gain based on the $4,400 you actually receive (minus your basis).

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Yuki Tanaka

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One option nobody's mentioned is to just redesignate that transfer retroactively. I'm also an S-Corp owner and my accountant told me I can document that initial transfer as a "shareholder advance" that will be counted toward my reasonable salary when I run payroll. Basically, you're pre-paying yourself, and when you run payroll, you just need to account for taxes and issue yourself a smaller net paycheck since you've already received most of the money. Just make sure your payroll service knows how to handle this correctly, and you'll need good documentation. I do this regularly - take money when I need it, then formalize it through payroll later.

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Is this really legit though? Don't you have to run actual payroll with proper tax withholdings at the time you take the money? I've been stressing about making sure everything is by-the-book with my new S-Corp.

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Yuki Tanaka

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This is absolutely legitimate as long as you properly document and account for everything. When you run payroll, you'll calculate the full gross salary amount, withhold all required taxes, and then reduce the net check by the amount you already advanced yourself. For example, if your reasonable salary is $5,000 monthly and you already took $3,000 as an advance, when you run payroll, you'll still calculate taxes on the full $5,000, but the net check would only be around $2,000 (minus the taxes on the full amount). This ensures all proper employment taxes are paid on your full reasonable compensation. Just make sure your payroll system can handle this "adjustment" or "reimbursement" properly.

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Klaus Schmidt

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My CPA told me this isn't actually as big a deal as people make it out to be for a new S-Corp with only a few months of operation. As long as you establish a reasonable salary before the end of the tax year and properly document everything, minor sequence mistakes in your first year typically won't trigger an audit. The reasonable compensation test is primarily looking at the entire tax year picture, not whether you took a specific distribution a few weeks before establishing payroll. Just don't make it a habit going forward!

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Aisha Patel

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Agreed! I did something similar my first year and my accountant just had me document everything carefully. The important thing is the year-end picture looks right. S-Corps get in trouble when they take massive distributions and tiny salaries over the course of entire years, not when they make minor timing errors while learning the ropes.

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