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Just to add another perspective here - NOL carryforwards from S-corps have some additional complexities people often miss. Remember that your ability to deduct the loss is limited by: 1) Your basis in the S-corp 2) At-risk limitations 3) Passive activity loss rules Without sufficient basis, you can't take the loss even if it flows through on the K-1. If your S-corp had debt that you personally guaranteed, that can increase your basis and allow more loss deduction.

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Thanks for bringing this up - I hadn't considered the basis limitations! Any simple way to calculate my basis? I've had the S-corp for about 5 years, started with $5K initial investment, and have been putting in some money each year to cover expenses (around $15K total over the years). Never taken any distributions.

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Your basis starts with your initial investment ($5K) and increases by any additional capital contributions ($15K) and any income that was reported to you on K-1s over the years. It decreases by losses and any distributions you took. So if you never took distributions, your basis would be $5K + $15K + any income reported on K-1s from previous years - any losses from previous years. You'll need to look at all your old K-1s to track this properly. If your basis went to zero in a previous year, any excess losses would be suspended and carried forward until you have basis again. This is separate from the NOL rules and often catches people by surprise.

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Yara Nassar

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Has anyone used TurboTax for handling NOL carryforwards from an S-corp? I'm in a similar situation and wondering if it can handle this correctly or if I need to go to a CPA.

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I tried using TurboTax for my S-corp NOL last year and it was a nightmare. It kept asking me questions that didn't make sense for an S-corp, and I don't think it properly tracked my basis. I ended up paying a CPA to fix everything and it cost me way more than if I'd just gone to them in the first place.

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Miguel Diaz

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Just a quick clarification that might help - the main reason Form 8606 is so important even though your 1040 numbers were correct is that it establishes your "basis" in the IRA. Without it, you risk getting taxed twice on the same money when you eventually take distributions. When you do backdoor Roth contributions yearly, each Form 8606 builds on information from previous years. That's why filing last year's form before doing this year's return is really important - the calculations carry forward.

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Amara Eze

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This makes so much sense, thank you! That was exactly my concern - that without documenting last year's basis correctly, I might mess up the calculations for this year. If I submit the standalone 8606 forms for last year now, should I wait to receive confirmation before filing this year's return? Or is it ok to go ahead and file as long as I've sent in the previous forms?

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Miguel Diaz

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You don't need to wait for confirmation from the IRS before filing this year's return. As long as you've submitted the prior year's Form 8606 before you file this year's return, you're in good shape. When completing this year's Form 8606, you'll use the basis information as if last year's form was properly filed, since you're now correcting that oversight. Just keep copies of everything you send to the IRS, including proof of mailing for the prior year forms. This documentation will be important if there are ever any questions about your IRA basis in the future.

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Zainab Ahmed

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Another tip - make sure you're using good tax software this year that specifically prompts you about Form 8606. I used FreeTaxUSA last year and it actually stopped me during the process and specifically asked about backdoor Roth conversions, making it impossible to miss the form.

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I second FreeTaxUSA for handling Backdoor Roth stuff! IRS Free Fillable Forms is just too easy to make mistakes with since it doesn't guide you through what forms you need based on your entries.

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Don't forget about Schedule SE for self-employment tax! Each partner will need to file this separately with their individual returns based on their K-1 income. My partner and I missed this our first year and got hit with penalties. The partnership itself doesn't pay self-employment tax, but each partner does on their share of partnership income.

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Sarah Ali

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Is self-employment tax really that significant? I'm also in a new partnership and trying to figure out if I should be making quarterly estimated payments.

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Ryan Vasquez

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For your marketing expenses - make sure you separate out meals if you took potential clients out for business discussions. Those are only 50% deductible while your other marketing costs are likely 100% deductible. Form 1065 has specific lines for this. The equipment you purchased might qualify for Section 179 expensing too, which lets you deduct the full cost immediately rather than depreciating it over several years.

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Mateo Silva

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This happened to me too! I freaked out when I saw strange banking info on my return from Jackson Hewitt. Make sure to ask Fiesta these questions: 1. What is the TOTAL fee including tax prep AND refund transfer fees? 2. When exactly will you get your money after the IRS sends the refund? 3. How will you receive the remaining funds? (direct deposit, check, prepaid card) They should have given you a document explaining all this before you signed your return. If they didn't, that's shady business practice and should be reported to the Better Business Bureau.

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Reporting to BBB does absolutely nothing fyi. They're not a government agency, just a private organization businesses pay to join. Filing a complaint with your state's attorney general office is way more effective.

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There's a form you were supposed to sign called a "Refund Authorization Form" or something similar that gives permission for this arrangement. Did they have you sign anything like that? If not, that's a big red flag. Check all your paperwork carefully. Also, just for future reference, there are free tax filing options that don't pull this refund transfer stuff. The IRS Free File program lets most people file for free if your income is under $73,000, and they don't play these games with your refund. Looking at section 35 is smart - always check where your money is going! Not a dumb question at all.

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Something nobody has mentioned yet - check if you can deduct it on your state taxes! Even if you can't benefit from itemizing on your federal return, some states have different rules or lower thresholds for medical expense deductions. For example, my state allows medical expense deductions that exceed just 4% of income instead of the federal 7.5%. Also, some states offer special credits for people with lower incomes who have high medical costs.

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That's a great point I hadn't considered! Do you know where I would find information about my state's specific rules for medical deductions? Is there a website that compares all the different state rules?

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The best place to check is your state's department of revenue or taxation website. Just google "[your state] department of revenue medical expense deduction" and you should find the official information. Each state has different rules, and they don't always match federal guidelines. Don't bother with websites that compare all states - they're often outdated. Your state's official tax website will have the current rules. You can also download your state's income tax forms and instructions, which usually explain the medical deduction rules in detail.

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One thing to consider - are you eligible for the Earned Income Tax Credit (EITC)? With an income of $22k, you might qualify for a refundable credit that could be more valuable than trying to deduct the dental expenses. Also, if your income is actually $22k from employment and you paid for the dental procedure yourself, you might look into an HSA for future medical expenses if your employer offers one. Too late for the current expense, but helpful for the future.

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The HSA suggestion isn't great for someone at this income level. You need a high-deductible health plan to qualify, and those can be risky for lower income folks. Plus HSAs don't typically work with dental unless it's medically necessary.

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