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Great question! I went through this exact same decision last year when I converted my LLC to S-Corp status. After researching and consulting with my tax professional, I ended up having my S-Corp pay 100% of my health insurance premiums. The math is pretty straightforward - at your $780/month premium ($9,360 annually), having the S-Corp pay saves you about $1,430 per year in FICA taxes (15.3% of $9,360). There's really no downside to going with 100% since you get the full deduction either way, but maximize your payroll tax savings. Just make sure you document everything properly. I have my S-Corp pay the insurance company directly each month, and my payroll service adds the premium amount to my W-2 wages (Box 1) but excludes it from Social Security and Medicare wages. Then I deduct the full amount on Line 17 of my personal return. One tip - if you're doing your own payroll, double-check that you're coding the health insurance correctly. It should be included in federal wages but excluded from FICA wages. I use QuickBooks Payroll and there's a specific payroll item for "Health Insurance (S-Corp >2% Owner)" that handles this automatically. With your $75k salary on $125k revenue, you're in a great position - very reasonable compensation ratio that won't raise any IRS eyebrows!
This is really helpful, thanks! Quick question about the documentation - when you say have the S-Corp pay the insurance company directly, do you set up some kind of automatic payment from your business account? I'm worried about missing payments or having timing issues if I'm manually handling this each month. Also, does it matter if the insurance policy is technically in my personal name vs the business name for tax purposes?
Great question about the logistics! Yes, I set up automatic ACH payments from my business checking account directly to my insurance company. Most insurers allow you to change the payment method online - I just logged into my portal and switched from my personal account to my business account. Set it to auto-pay a few days before the due date to avoid any timing issues. The policy can absolutely stay in your personal name - that doesn't matter for tax purposes at all. What matters is who's paying the premiums and how it's documented. I keep a simple spreadsheet tracking each month's payment with the date, amount, and insurance company, plus I save the bank statements showing the business account payments. My insurance company also emails me payment confirmations each month, which I save in a folder for tax documentation. The key is just having a clear paper trail showing your S-Corp paid the premiums directly to the insurer. Much cleaner than the reimbursement method and eliminates any potential issues with timing or documentation gaps.
One thing I haven't seen mentioned yet is the impact on your Affordable Care Act (ACA) compliance if you ever have employees. Right now as a single-member S-Corp you're fine, but if you plan to hire employees in the future, you'll want to make sure your health insurance arrangement doesn't create complications with ACA employer mandate requirements. Also, don't forget that if you have a spouse who could potentially be covered under your plan, the S-Corp can pay for family coverage too and you'd get the same FICA tax savings on the entire premium amount. Just make sure any family members covered are properly reflected in your documentation. The 100% S-Corp payment approach is definitely the way to go for maximizing your tax benefits. At your income level and premium amount, you're looking at saving around $1,430 annually in payroll taxes compared to paying personally - that's basically 1.8 months of free health insurance!
This is a great point about future employees! I'm actually considering hiring a part-time assistant next year, so I hadn't thought about how that might complicate things. Do you know if there's a specific employee threshold where ACA requirements kick in, or is it immediate once you have any employees? Also, regarding the spouse coverage - that's really interesting. My spouse currently gets insurance through their employer, but their premiums are pretty high. Would there be any issues with them dropping their employer coverage to join my S-Corp plan, or any coordination of benefits complications I should be aware of? The potential to get FICA savings on family coverage could be substantial given how expensive family plans are.
Great thread with lots of helpful information! I just completed my Form 706NA payment process last week and wanted to share a few additional tips that might help others: 1. Double-check your bank account information before submitting - I made a typo in my routing number initially and had to start over. The IRS system caught it during verification, but it delayed my payment by several days. 2. If you're making a large payment (like the $34,500 mentioned in the original post), some banks have daily ACH limits that might prevent the transaction from going through. I had to call my bank to temporarily increase my limit for the estate tax payment. 3. Keep multiple copies of your confirmation page and save it as a PDF. I printed three copies and emailed the PDF to myself as backup. The confirmation number is crucial if you ever need to trace the payment. The whole process was actually smoother than I expected once I figured out the right options to select. The key is just being very careful about the tax year selection (as Vanessa mentioned) and making sure all your information is exactly correct before hitting submit.
Thanks for these practical tips! The bank daily limit issue is something I never would have thought about. I'm dealing with a similar situation where the estate owes around $28,000, and my bank does have ACH limits. Did you have to provide any special documentation to your bank to increase the limit temporarily, or was it just a phone call? I want to make sure I have everything ready before I attempt the payment since I'm already cutting it close to the deadline.
@CyberSamurai For my bank, it was just a phone call to their business banking department (since I was acting as executor). I explained that I needed to make a one-time IRS estate tax payment and they temporarily raised my ACH limit for 48 hours without any additional documentation. However, different banks have different policies - some might require you to provide a copy of your letters testamentary or proof that you're the authorized representative for the estate. I'd recommend calling your bank a day or two before you plan to make the payment, just to be safe. Some banks can make the change immediately over the phone, while others might need 24 hours to process the limit increase. Given that you're close to the deadline, definitely don't wait until the last minute to sort this out! Also, if your bank gives you any trouble, you could consider using a wire transfer instead, though that typically comes with higher fees. The important thing is getting the payment submitted on time.
I went through this exact process about 6 months ago and can confirm that the Direct Pay method works well for Form 706NA. One thing that really helped me was calling the IRS taxpayer assistance line beforehand to confirm I was selecting the right options - they verified that using "Form 706" in the system covers both regular 706 and 706NA filings. A few additional tips from my experience: - Make sure you have the estate's EIN ready before starting the payment process - The system will ask for the "primary taxpayer" - use the decedent's name exactly as it appears on the 706NA form - If you're making the payment close to the due date, consider doing it in the morning rather than late at night to avoid any potential system maintenance windows The confirmation email came through within about 10 minutes, and I was able to track the payment status through my bank. The whole process took less than 15 minutes once I had all the information ready. Don't stress too much about it - the IRS payment system is actually pretty straightforward once you know which buttons to click!
This is really helpful, thank you! I'm just starting this process and feeling overwhelmed. Quick question - when you called the IRS taxpayer assistance line, how long did it take to get through? I've been dreading having to call them because I keep hearing horror stories about multi-hour wait times. Did you have any specific number you called or just the general taxpayer assistance line? I want to get confirmation before I submit my payment too, but I'm worried about spending my whole day on hold.
@Javier Morales I actually used Claimyr mentioned (earlier in this thread by Max Knight to) get through to the IRS. After reading about it here, I figured it was worth trying since I was dreading the wait times too. Got connected in about 25 minutes, which was way better than the 3+ hour waits I d'experienced trying to call directly. If you don t'want to use a service like that, I d'suggest calling the main taxpayer assistance line 1-800-829-1040 (early) in the morning - like right at 7 AM when they open. That seems to be when wait times are shortest. But honestly, for estate tax questions, the representatives are usually pretty knowledgeable and it s'worth getting confirmation before you submit a $28k+ payment. The peace of mind is worth whatever method gets you through fastest!
Has anyone dealt with reporting a deceased person's mortgage interest deduction on a partial year return? My brother passed away last spring and I'm trying to figure out if I need to prorate the mortgage interest or just take the full amount shown on his 1098.
For a deceased taxpayer, you'd report all the mortgage interest paid during the period they were alive on their final tax return. You don't need to prorate the amount shown on the 1098 - just report whatever interest was actually paid before their death. The 1098 should show the total interest paid for the year up to the date of payoff or through December if the mortgage continued.
I'm sorry for your loss and understand how confusing this must be while handling your father's estate. As others have mentioned, the OMP discrepancy is likely just a system reporting error since you have documentation showing the mortgage was paid off and were able to sell the house without issues. For the final tax return, you'll want to report the mortgage interest that was actually paid during the time your father was alive (January through November). The key document here is that "paid in full" letter you mentioned - keep that with the tax records as supporting documentation. The IRS understands that 1098 forms sometimes contain errors, especially in situations involving payoffs or deceased taxpayers. If you're concerned about potential questions from the IRS, you might consider attaching a brief explanation to the return noting that the mortgage was paid off in August (with the paid-in-full letter as proof) and that the OMP figure on the 1098 is incorrect. This kind of proactive documentation can save headaches later if there are any audit questions.
This is really helpful advice, thank you. I'm dealing with something similar with my grandmother's estate and the proactive documentation approach makes a lot of sense. Would you recommend including a copy of the paid-in-full letter directly with the tax return, or just keeping it in our records in case we need it later? I want to make sure we're being thorough but not overwhelming the IRS with unnecessary paperwork.
Call JH customer service and get a tracking number for the check. They can usually provide that
been on hold for like an hour tryna do that š
Ugh the hold times are insane! I'd honestly just check out that taxr.ai thing everyone's mentioning - seems way faster than waiting on hold forever just to get a tracking number
Same exact situation happened to me with Jackson Hewitt! They put in the wrong routing number for my refund advance and it took exactly 8 business days from when the deposit got rejected to when I received the paper check in the mail. The check came via regular mail, not certified or anything, so just keep checking your mailbox daily. JH should have sent you an email or text confirming they're sending a paper check - if you didn't get that notification, definitely call them to confirm your mailing address is correct!
Yuki Ito
Question - have you checked the SBTPG site using both mobile and desktop? Their site is janky AF and sometimes shows different info depending on how you access it. On my phone it showed no trace number but on desktop it was there! worth a try
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Keisha Robinson
ā¢I haven't tried that! Will check on my laptop when I get home. Their mobile site is terrible.
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Honorah King
I'm going through the exact same thing right now! Filed in early March, got accepted, transcript shows 846 code with April 1st issue date, but SBTPG has been showing a blank trace number field for over two weeks. It's so stressful when you're counting on that money. I've been checking their site multiple times a day hoping something will show up. Based on what everyone's saying here, it sounds like this is unfortunately pretty common with SBTPG this year. I'm going to try calling the IRS tomorrow morning and see if they can give me any insight into what's actually happening on their end. Really hoping we both get some answers soon - the waiting is killing me!
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Paolo Ricci
ā¢I feel your pain! I'm dealing with something similar - my transcript shows the refund was issued but SBTPG just has that frustrating blank space where the trace number should be. It's so nerve-wracking when you need that money for bills. From reading through all these comments, it seems like SBTPG is having major issues this year. Some people are saying to call the IRS directly since they can see what's actually happening behind the scenes. I might try that myself if nothing shows up by the end of this week. Fingers crossed we both get some movement soon! š¤
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