IRS

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Ask the community...

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  • DO NOT post call problems here - there is a support tab at the top for that :)

Chris Elmeda

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Make sure you check if you qualify for Head of Household status even while separated! I was separated for 9 months last year, had my kids more than half the time, and paid over half the household costs. My accountant filed me as HOH even though I was technically still married, and it saved me almost $3,800 compared to Married Filing Separately. The key requirements: you need to be "considered unmarried" which means: 1) file a separate return, 2) paid more than half the cost of keeping up your home, 3) your spouse didn't live in your home during the last 6 months of the tax year, and 4) your home was the main home of your child for more than half the year.

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This is really helpful. I think I might not qualify since the kids are primarily with their mom, but I'll double check the requirements. Do you know if there's any documentation I need to keep in case the IRS questions my filing status?

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Chris Elmeda

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You should definitely keep records showing when your separation began - any legal separation documents, lease agreement for your apartment showing when you moved out, and anything documenting your custody arrangement. Also save records of all household expenses you paid (rent/mortgage, utilities, repairs, food, etc.) to prove you paid more than half the cost of keeping up a home if you try to claim Head of Household. If the kids are primarily with their mom, you probably won't qualify for HOH. But if she's willing, she could release the dependency exemption to you using Form 8332 (though she'd still claim HOH). This form specifically allows the custodial parent to release the child's exemption to the non-custodial parent.

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Jean Claude

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Don't forget that your filing status affects your stimulus eligibility too! When my ex and I separated in 2022, we filed separately and I missed out on part of a stimulus payment because they used our old joint income. Check if you received all eligible stimulus payments and recovery rebate credits based on your new separate income situation.

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The stimulus payments were years ago though? I don't think there have been any since 2021. Are you saying we can still claim them somehow if we didn't get the right amount back then?

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Niko Ramsey

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One important thing to remember when you're a contractor vs. employee: no one is withholding taxes for you! I made this mistake my first year freelancing and got hit with a huge tax bill plus penalties. Make sure you're setting aside around 30% of your income for taxes and making quarterly estimated payments.

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Is it really 30%? That seems crazy high! Do you really need to set aside that much? I just started freelancing and haven't been saving nearly that amount...

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Niko Ramsey

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The 30% is a safe estimate that covers federal income tax, state income tax (depending on your state), and self-employment tax (which is 15.3% alone). It's better to save too much than too little. Your actual rate will depend on your total income, deductions, credits, and state. If you're in a high-income bracket and a high-tax state, it could actually be higher than 30%. If you're in a lower bracket or a state with no income tax, you might need less. But starting with 30% is usually a good rule of thumb for most freelancers.

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Jabari-Jo

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Quick question - if the LLC I'm working for is classified as an S corporation, does that change anything for me as a contractor filling out a W-9?

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Nope, their classification doesn't affect yours. You're still an individual/sole proprietor regardless of how the entity paying you is structured. Their business structure only matters for their taxes, not yours.

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IRS says my deceased father's unpaid tax bill could be covered by unfiled returns - can I still claim them?

I'm dealing with a messy situation with my father's estate and hoping someone can help. My dad passed away in December 2022 and I've been trying to settle his tax affairs for the past year and a half. I filed his final 1040 for 2022 in early 2023 with all the estate forms. There was actually a refund due, but it never showed up. After waiting several months, I made an in-person appointment at the IRS office last summer to figure out what happened. That's when the bombshell dropped - they told me my dad hadn't filed his 2019 taxes and there was an outstanding balance from that year. Apparently, that's why they were holding the 2022 refund. A few months later, I received a notice showing the 2019 balance plus interest (around $3,800 total now). The estate doesn't have liquid funds to cover this. I made another IRS appointment last month, and it got even more confusing. The agent said my dad HAD filed 2019 taxes initially, but the IRS later discovered unreported income and assessed additional tax. They sent a notice about this in October 2022, which he probably never saw since he died shortly after. Here's where it gets interesting - the agent also discovered my dad never filed for 2020 or 2021, and based on the income information they have, he would have been owed refunds totaling around $8,500 for those years - more than double what he owes for 2019! But the agent said I'm out of luck because there's only a 3-year window to claim refunds. She suggested I could still file the missing returns and then appeal, but meanwhile, that 2019 balance keeps accruing interest. Can anyone advise me on how to handle this? Is there any way to get the IRS to apply those potential refunds to the outstanding balance, even though we're outside the 3-year window?

Don't forget to see if your father's situation qualifies for First Time Penalty Abatement! If he had a clean compliance history (filed and paid on time) for the three years before 2019, you might be able to get the penalties removed entirely. This would at least reduce the overall amount owed. You'd need to call the IRS and specifically ask for "First Time Penalty Abatement" for the unfiled return. The interest would still apply, but removing penalties could significantly reduce the total.

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Yara Assad

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That's a great suggestion I hadn't considered. My dad was always pretty diligent about filing on time before he got sick, so he probably would qualify. Do I need to file a specific form for this abatement request or just call and ask for it?

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You don't need a specific form for First Time Penalty Abatement. The easiest approach is to call the IRS directly and make a verbal request. Make sure to specifically use the phrase "First Time Penalty Abatement" when speaking with the representative. If you prefer to request it in writing, you can submit a penalty abatement letter that clearly states you're requesting First Time Penalty Abatement. Include your father's name, SSN, the specific tax year (2019), and a statement confirming that he had a history of compliance for the three prior years. Attach a copy of the death certificate as well.

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Just a heads up - I'd recommend filing those unfiled returns ASAP. Even though the 3-year refund window might have passed, there's actually no statute of limitations for the IRS to ASSESS taxes if returns were never filed. So better to file them showing refunds owed than risk the IRS creating Substitute for Returns (SFRs) that might not include all deductions and credits he was entitled to.

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This is so true. My brother never filed his 2017 taxes and the IRS created a substitute return for him in 2022 that assessed over $12,000 in taxes because they only counted income and NONE of his deductions or credits. He would have actually been due a refund if he'd filed properly. Don't wait!

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Don't delay filing your 1065! I made this mistake last year thinking I could just handle it later since we didn't have much activity, and the penalties added up fast. If you file now, you might qualify for first-time penalty abatement if you haven't had issues in the past. Also, file IRS Form 7004 right away for an automatic extension to September 15, which will stop additional penalties from accruing. You'll still owe penalties for missing the March deadline, but it prevents making the situation worse.

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Thanks for this advice. Is filing Form 7004 for an extension still helpful even though I've already missed the original March deadline? And do you know if first-time penalty abatement is something I can request myself or do I need a tax professional to help with that?

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Yes, filing Form 7004 is still helpful even after missing the deadline! It prevents additional penalties from accruing after the original due date. So while you'll still owe penalties for the period between March 15 and when you file the extension, you won't accumulate more penalties through September. First-time penalty abatement is something you can absolutely request yourself - you don't need a professional. After you file the late return, call the IRS business line and simply ask for "first-time penalty abatement." If you have a clean compliance history (no penalties in the past 3 years), they will often grant it over the phone. Just be polite and explain that you weren't aware of the filing requirements since this was your first year with actual business activity.

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Dmitry Popov

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If ur LLC is just 2 members, have u considered filing as an S-Corp instead? Could save u on self-employment taxes. U missed the deadline for 2023 but could elect for 2024. We did this with our small business and saved about 5k in taxes last year by paying ourselves reasonable salaries and taking the rest as distributions.

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That's not entirely accurate. S-Corps save on SE taxes but they have more compliance requirements like payroll tax filings and reasonable salary documentation. Plus the OP would need to file Form 2553 to elect S-Corp status, and retroactive elections can be tricky. Not worth the headache for a small LLC that's just starting out in my opinion.

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Don't forget about the safe harbor rules for quarterly taxes! As long as you pay 100% of last year's tax liability (or 90% of this year's), you won't face penalties even if you underpay a bit. Since this is your first year freelancing, you could potentially just pay in quarterly installments whatever you paid in total taxes last year, and you'd be safe from penalties. That might be easier than trying to calculate everything precisely.

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That's really helpful! But what if I didn't pay any taxes last year because I was a student and didn't have income? Does that mean I don't have to pay anything for this year's quarterly taxes, or am I misunderstanding the safe harbor rule?

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If you didn't have any tax liability last year, then technically 100% of last year's tax would be $0. However, in this situation, you'd need to use the other safe harbor provision of paying 90% of what you'll owe this year. Since this is your first year with self-employment income, you do need to make estimated quarterly payments. But the good news is that with your relatively low income level around $6,800, your total tax obligation won't be very high. You might actually qualify for certain deductions and credits that could significantly reduce what you owe.

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Omar Fawzi

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I'm also new to freelancing and quarterly taxes. Quick question - I've been hearing about the 1099 form. Will my clients send me those, or do I create them myself? And what do they have to do with quarterly taxes?

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NebulaNomad

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Your clients should send you a 1099-NEC form (for Non-Employee Compensation) if they paid you $600 or more during the year. You don't create these yourself. However, whether you receive 1099s or not, you're still required to report all your income and pay quarterly taxes on it. The 1099s are basically just documentation of what you earned, but you should be keeping track of all your income regardless of whether you get these forms. For calculating quarterly taxes, you'll estimate your annual income and tax liability based on your earnings, then divide by 4 to determine your quarterly payments.

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