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Ask the community...

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Has anyone filed a Form 709 electronically? When I go through TurboTax or H&R Block software, they seem to handle income tax returns but not gift tax returns. Am I missing something, or do these forms still need to be filed on paper?

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Malia Ponder

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Unfortunately, Form 709 cannot be e-filed yet. I just completed mine last month for a similar situation, and it has to be filed on paper. I was surprised too, since almost everything else can be done electronically now! Make sure to send it via certified mail so you have proof of timely filing. Also, don't attach it to your Form 1040 (income tax return) - it needs to be mailed separately to the specific address for gift tax returns.

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Great question about Form 709! I went through this exact situation last year when I sold my townhouse to my nephew for $180k when it was worth $420k. One crucial detail that hasn't been mentioned yet - make sure you understand the timing requirements. Form 709 is due by April 15th of the year following the gift (so April 15, 2025 for your 2024 transaction). However, if you request an extension for your income tax return, it automatically extends your Form 709 deadline to October 15th. Also, since your gift amount ($405k) exceeds the 2024 annual exclusion of $18,000, you'll definitely need to file Form 709 even if you don't owe any gift tax due to the lifetime exemption. The IRS wants to track these large gifts against your lifetime exclusion amount. One more tip - if this is your first Form 709, make sure to include a clear cover letter explaining the transaction. The IRS appreciates transparency, and it can help avoid follow-up questions later.

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Rajiv Kumar

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Thank you for mentioning the timing requirements! I had no idea about the automatic extension if you extend your income tax return. That's really helpful since I'm still gathering all my documentation. Quick question about the cover letter - what specific details should I include? Should I explain the family relationship, the reason for the below-market sale, and how I calculated the FMV? I want to be thorough but not overwhelm them with unnecessary information. Also, does anyone know if there's a specific format the IRS prefers for the cover letter, or is a simple business letter format sufficient?

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Has anyone used Drake Tax software for this situation? I'm preparing several S Corp returns with SEP contributions and Drake seems to automatically put the current year's contribution (made in the following year) on Line 17, but I want to make sure it's handling it correctly.

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Ravi Kapoor

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I use Drake for all my S Corp clients and it handles this correctly. When you enter the retirement plan contribution, there's a field to specify which tax year the contribution applies to. Drake will then put it on Line 17 of the appropriate year's return, regardless of when it was actually paid.

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Thanks for confirming! That's exactly what I needed to know. I was worried I might need to manually override something, but sounds like Drake has this covered as long as I specify the tax year correctly.

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Oliver Weber

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This is such a common source of confusion! I went through the exact same thing when I started handling my family's S Corp taxes. The key insight that finally clicked for me is that SEP contributions are one of the few exceptions to the normal cash-basis timing rules. Think of it this way: the IRS wants to encourage retirement savings, so they created special timing rules that let you make the contribution after year-end but still deduct it for the previous tax year. This gives you time to see your final numbers before deciding on the contribution amount. Just make sure when your brother makes that 2023 SEP contribution in March 2024, he tells the financial institution it's specifically for tax year 2023. They should give you some kind of documentation confirming this designation. Then that amount goes on Line 17 of the 2023 Form 1120S, even though the cash won't leave the business account until 2024. The deadline for making the contribution is the same as the filing deadline for the return (including extensions), so you have plenty of time to get it sorted out.

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Ravi Sharma

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This is really helpful! I'm new to handling business taxes and was getting overwhelmed by all the different timing rules. Your explanation makes it much clearer - the SEP contribution exception exists specifically to encourage retirement savings, which makes sense from a policy perspective. One follow-up question: when you say the deadline is the same as the filing deadline including extensions, does that mean if I file for an extension on the 1120S, I have until October to make the 2023 SEP contribution? Or does it have to be made by the original March deadline regardless of extensions?

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Aisha Jackson

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Just to clarify something important - TurboTax itself isn't usually making calculation errors. What typically happens is either: 1) users enter information incorrectly, 2) users misunderstand eligibility requirements, or 3) the IRS makes adjustments based on information they have that wasn't included in your return. For example, if you have unreported income that shows up on a 1099 the IRS received but you didn't include, they'll adjust your return accordingly.

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I appreciate everyone sharing their experiences here. As someone who's been doing taxes for family members for years, I can confirm that most discrepancies aren't actually TurboTax errors but rather eligibility issues or data entry mistakes. That said, I always recommend using the IRS's own Interactive Tax Assistant (ITA) tool on their website to verify credit eligibility before filing. It's free and walks you through the exact same qualification questions the IRS uses. Also, for peace of mind, you can request a tax transcript after filing to see exactly what the IRS processed vs what you submitted. The key is understanding that tax software is only as accurate as the information you provide and your actual eligibility for credits.

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Kai Santiago

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Has anyone used the Household Employment Tax section in TurboTax? I find it super confusing because it asks for the total wages I paid my nanny, but I'm not sure if that should include the taxes I paid to Poppins or just her direct wages?

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You should only enter the direct wages you paid to your nanny, not the taxes you paid. The taxes you paid through Poppins go in a different section (the estimated tax payments section we discussed above).

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Zara Shah

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One thing that helped me was getting a copy of the actual tax deposits Poppins made on my behalf throughout the year. They should be able to provide you with a summary showing the exact dates and amounts of each federal tax deposit they made. This makes it much easier when entering the estimated tax payments in TurboTax because you can enter each payment with the correct date it was actually submitted to the IRS. Also, double-check that Poppins handled both the employer and employee portions of Social Security and Medicare taxes correctly. Sometimes there can be confusion about which taxes were withheld from your nanny's pay versus which ones you paid as the employer. The Schedule H should reconcile everything, but having that detailed breakdown from your payroll service makes the whole process much smoother.

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This is really helpful advice! I'm new to the household employer thing and didn't even think about getting the detailed deposit records. Quick question - when you say "employer and employee portions" of Social Security and Medicare, does that mean I'm responsible for both parts? I thought the employee portion would come out of my nanny's wages automatically?

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Has anyone dealt with getting a severance paid out over multiple payments instead of one lump sum? My company is offering me either option, and I'm wondering if taking it over 3 months would result in less tax withholding upfront compared to a lump sum.

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I chose the multiple payment option when I was laid off last year, and it definitely helped with the tax withholding situation. When they break it up, each payment is smaller, so the withholding system doesn't treat each payment as if you're suddenly in a super high tax bracket. The downside is that you're at the mercy of the company continuing to make those payments. If they have financial troubles, your later payments could be at risk. Also, some benefits might end after the first payment rather than continuing through all payments, depending on your severance agreement.

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Thanks for sharing your experience! That's exactly what I was hoping would happen with the taxes. I'm not too worried about the company's financial stability, they're pretty large. Did you notice any difference in how your final tax return worked out? Did you still get a refund even with the lower withholding on the multiple payments?

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I went through something very similar when I got laid off six months ago. The 58% withholding rate you're seeing is unfortunately pretty normal for severance payments, especially if your company is being conservative with their calculations. Here's what likely happened: Your company treated the $8,500 severance as if you were going to receive that amount every pay period for the entire year. So if you normally get paid bi-weekly, they calculated withholding as if you'd be making $221,000 annually ($8,500 x 26 pay periods). That would put you in a much higher tax bracket, hence the aggressive withholding. The silver lining is that when you file your 2025 tax return, your actual tax will be based on your total income for the year - which will likely be much lower since you're now unemployed. You should get a substantial refund of that overwithholding. I'd recommend requesting a detailed breakdown of all the withholdings from HR so you can see exactly where every dollar went. Sometimes there are errors or unnecessary deductions that you can get corrected. Also consider talking to a tax professional about estimated quarterly payments for the rest of 2025 to avoid more overwithholding when you find your next job.

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Evelyn Kim

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This is really helpful, thank you! The explanation about them treating it as if I'd make that amount every pay period makes so much sense now. I was wondering why the withholding seemed so extreme. I'm definitely going to request that detailed breakdown from HR. Based on what others have shared in this thread, it sounds like there might be some incorrect deductions I can get back right away, plus the larger refund when I file next year. Do you have any recommendations for finding a good tax professional? I've always done my own taxes with software, but this situation seems complex enough that I might need actual help for once.

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ShadowHunter

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For finding a tax professional, I'd recommend looking for an Enrolled Agent (EA) or CPA who specifically has experience with employment transitions and severance situations. You can search the IRS directory for Enrolled Agents in your area, or check with your state's CPA society for referrals. Many tax pros offer free consultations this time of year, so you could potentially get some initial guidance without committing to hiring someone. Given that your situation involves severance, potential overwithholding, and job transition, it's probably worth the investment to make sure you're maximizing your refund and properly planning for the rest of the tax year. Also, don't forget to keep detailed records of any job search expenses - some of those may be deductible depending on your situation.

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