IRS

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Ask the community...

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3 Just throwing this out there, but have you checked with your accountant? Most business accountants can e-file the extension for you quickly and it's usually not very expensive. They do this routinely. Might be the simplest solution if you're in a time crunch.

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1 I actually don't have an accountant yet - part of why I'm in this mess! Been trying to handle everything myself to save money in the first year, but clearly that's not working out so well. Do accountants typically take on new clients same-day when there's a deadline?

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3 Many accountants do offer same-day extension filing for new clients, especially during tax season. It's a common way they begin relationships with new business clients who are in a bind. A simple extension filing is low-risk for them and gives you both a chance to work together. I'd recommend calling a few local business accountants and explaining your situation. Be clear that you need the Form 7004 filed today and ask if they can help. Even if they can't take you on as a full client right away, many will handle just the extension filing to help you meet the deadline.

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14 Remember that even if you file the extension, you still need to pay any estimated taxes due with the extension to avoid penalties! The extension only gives you more time to file the paperwork, not to pay what you owe.

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1 Oh crap, I didn't realize that! I haven't calculated what I might owe yet. Is there a quick way to estimate this, or do I need to basically do all the tax calculations anyway?

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14 You don't need to do the complete calculations, but you should make a reasonable estimate based on your business income and expenses for the year. A safe approach is to look at what you paid last year (if you were in business) and pay at least that amount. If this is your first year, calculate your rough profit and multiply by the appropriate tax rate. If you're really unsure, it's generally better to overpay slightly and get a refund later than to underpay and face penalties. Even a good faith estimate shows the IRS you're trying to comply, which can help if you end up slightly short.

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As someone who moved from the UK to New York and then to Florida with a similar income level, let me tell you the difference in take-home pay is MASSIVE. In NY, I was paying: Federal: ~32% effective NY State: ~7% NYC local: ~4% Plus limited SALT deductions Moving to Florida, I immediately got a "raise" of about $60k just from eliminating state and city taxes. No action required on my part - just more money in my pocket.

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Zara Ahmed

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But Florida has higher property taxes and insurance costs, right? Did that eat up some of the tax savings?

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Don't overlook retirement accounts as a tax strategy! Max out your 401k contributions ($23,000 in 2025) as soon as you arrive. For someone in your tax bracket, that's an immediate tax savings of around $8,500 just on the federal side. Also look into backdoor Roth IRA contributions since you'll be over the income limits for direct contributions.

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Nia Thompson

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Can new residents immediately contribute to 401ks? I thought there might be waiting periods or residency requirements for tax-advantaged accounts.

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There are no residency requirements for 401k eligibility from a tax perspective - it's based on your employment status, not your citizenship or residency history. As soon as you're legally authorized to work in the US (with appropriate visa/work permit) and your employer offers a 401k plan, you can contribute. Some employer plans do have waiting periods before you're eligible (commonly 3-6 months), but that's a company policy issue, not a tax or legal requirement. Your employer may also have a vesting schedule for their matching contributions, but your personal contributions are always 100% vested. The key thing is having a Social Security Number or Tax ID Number, which you'll need anyway for employment.

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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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