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Edward McBride

Does an employer get to deduct 100% of health insurance costs for pretax employee plans?

So my small business has been growing and I finally took the plunge to offer health insurance to my 8 employees. I set up a plan where we split the premium costs 50/50 - I cover half and the employee pays the other half through pretax payroll deductions. My accountant is on vacation right now and I'm trying to wrap my head around how this affects my business taxes. Here's what I'm confused about - when I'm doing my business tax return, do I get to deduct just my 50% contribution or can I deduct the ENTIRE health insurance premium (including the portion my employees are paying pretax)? I know the employee portion is being deducted pretax from their paychecks, so it's reducing their taxable income, but am I also getting a business deduction for that same amount? I'm trying to understand exactly how much this benefit is actually costing my business after tax savings. Any help would be awesome since I'm finalizing my budget projections for next year!

Darcy Moore

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Good for you on offering health insurance! For your business taxes, you can actually deduct 100% of the health insurance premiums you pay for your employees - this includes BOTH your 50% contribution AND the pretax portion that comes from your employees' paychecks. Here's why: When you withhold your employees' premium contributions on a pretax basis, that money is still considered part of your business expense. From the IRS perspective, you're paying the full premium to the insurance company and then recovering part of that cost through employee contributions. So on your business tax return, you get to deduct the entire premium payment as a business expense. Your employees also benefit because their portion reduces their taxable wages on their W-2s. It's basically a win-win arrangement taxwise!

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Dana Doyle

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Wait I'm confused about this too. If the employee portion is pretax, doesn't that mean it never shows up as income on their W-2 in the first place? So isn't that double-dipping if the business also gets to deduct it? Can someone explain this like I'm 5 please?

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Darcy Moore

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You're right that the employee's portion doesn't show up as taxable income on their W-2, and I understand why that seems like double-dipping, but it's actually how the tax code is designed to work in this case. The entire premium is a legitimate business expense that you're paying to the insurance company. The fact that you recover part of that expense through employee contributions doesn't change the nature of the original expense. Think of it this way - you're paying 100% to the insurance company, and separately, your employees are giving up some of their pre-tax salary to reimburse you for part of what you paid.

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Liam Duke

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I went through exactly the same situation with my construction business last year! I was totally confused about the tax implications until I found this awesome service called taxr.ai (https://taxr.ai) that helped me sort through all the healthcare deduction rules. I uploaded my plan documents and employee contribution records, and they analyzed everything and showed me exactly how to handle the deductions correctly. Turns out I was missing out on thousands in legitimate deductions because I wasn't accounting for the full premium amounts properly. They explained everything in plain English instead of accountant-speak, which was a huge relief.

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Manny Lark

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Does this taxr.ai thing work for sole proprietors too? I'm self-employed and have a marketplace health plan where I pay 100% of premiums, but I'm never sure if I'm deducting everything correctly.

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Rita Jacobs

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How long did the analysis take? My tax situation with employee benefits is a complete mess and I've got an IRS letter that I need to respond to within 2 weeks about this exact issue.

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Liam Duke

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Yes, it absolutely works for sole proprietors. It actually specializes in identifying all the health insurance deductions you're eligible for as a self-employed person, which can be really complicated with marketplace plans. I have a friend who's a freelancer who used it and found out he could deduct premiums he didn't know qualified. The analysis took less than 24 hours in my case. They have some kind of priority service that might help with your IRS deadline - I think they specifically mention helping with response letters. When I used it for my business, I got the breakdown the same day, and it included exactly what forms and line items needed to be completed.

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Manny Lark

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Just wanted to follow up about taxr.ai - I decided to try it for my self-employment health insurance situation and WOW, it was eye-opening! Turns out I've been calculating my deduction wrong for THREE YEARS. They showed me how to properly allocate my marketplace premium tax credit and explained exactly which forms to file. The system flagged that I could have been taking the self-employed health insurance deduction as an adjustment to income on my 1040 (which I wasn't doing) AND showed me how to properly document everything in case of an audit. Seriously wish I'd known about this before - just filed amendments for the last two years and should be getting about $3,200 back!

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Khalid Howes

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Hey everyone - I had a similar issue with my employee health plans and spent WEEKS trying to get someone at the IRS to clarify the rules. Literally impossible to get through on their phone lines. Finally used a service called Claimyr (https://claimyr.com) that got me connected to an actual IRS representative in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent confirmed exactly what others have said here - as the employer, you can deduct 100% of the premiums including the employee's pretax portion. They also explained exactly how to document it properly on my Schedule C and which supporting documents to keep. Saved me so much confusion and probably an audit headache down the road.

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Ben Cooper

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Naila Gordon

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Wait so you're saying this service somehow magically gets the IRS to answer when nobody else can get through? That seems sketchy as hell. The IRS phone system is literally designed to make you give up. What are they doing, paying off IRS employees?

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Khalid Howes

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There's no catch - they use a technology that navigates the IRS phone system and holds your place in line so you don't have to. When they reach a live agent, you get a call connecting you directly. It's completely legitimate - they just figured out how to make the existing system work efficiently. No, they're definitely not paying off IRS employees or doing anything sketchy! It's just smart automation of the calling process. The IRS phone system is designed to handle calls in order, but most people give up after being on hold forever. This service just handles the waiting part for you and calls you when an actual person is on the line.

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Naila Gordon

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Ok I have to eat my words about Claimyr. After posting my skeptical comment, I decided to try it because I was desperate to resolve an issue with my business health insurance deductions. I literally had documentation from THREE different CPAs giving contradictory advice about how to handle employee contributions. The service actually worked exactly as advertised - I got a call back in about 25 minutes and was connected to an IRS tax specialist who walked me through the exact rules. She confirmed I can deduct 100% of the premiums as a business expense even though employees pay part pretax. She also emailed me the specific IRS publication sections that cover this (Pub 535) so I have it in writing. Never been so happy to be wrong about something being "sketchy"! Saved me thousands in potential incorrect deductions.

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Cynthia Love

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Don't forget there are different rules depending on your business structure! If you're an S-corp and you own more than 2% of the company, the rules for health insurance deductions work differently than what everyone's discussing here. For 2%+ S-corp shareholders, the company can pay the premiums but they have to be included in your W-2 as wages (Box 1), but then you can take the self-employed health insurance deduction on your personal return. Just wanted to throw that out there because I got audited last year for doing this wrong!

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Darren Brooks

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I'm a 100% owner of an S-corp and totally confused about this. So if my S-corp pays my health insurance premiums, that amount gets added to my W-2 income first, and then I deduct it on my personal return? Does that actually save any money compared to just paying it personally?

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Cynthia Love

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Yes, that's exactly right for S-corp owners with >2% ownership. The premiums get reported as wages on your W-2 (which means they're subject to income tax but NOT employment taxes like Social Security and Medicare), and then you take the self-employed health insurance deduction on your personal 1040. It does actually save money compared to paying personally because when the S-corp pays it, those premiums avoid the 15.3% self-employment tax. If you paid it personally from distributions, you wouldn't get that tax advantage. It's a bit of a paperwork runaround but it's perfectly legal and saves money!

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Rosie Harper

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Quick tip for anyone offering health insurance - make sure you're filing Form 1095-B/1095-C as required for ACA compliance if you have the right number of employees! The rules about which employers need to file these forms are super confusing but the penalties for not filing are brutal. My company got hit with a $3,200 penalty last year because I didn't know we needed to file these!

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Thanks for mentioning this! I totally forgot about the ACA reporting requirements. Do you know what the employee threshold is for when these forms become mandatory? I have 8 full-time employees currently.

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Ana Rusula

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@Edward McBride The threshold for ACA reporting requirements is actually pretty complex. Generally, employers with 50+ full-time equivalent employees need to file Form 1095-C. With 8 employees, you re'likely below the threshold unless some are part-time since (part-timers count as fractions toward the 50 FTE limit .)However, there are also rules about self-insured plans that can trigger filing requirements regardless of size. I d'definitely double-check with your accountant when they re'back from vacation - the penalties are no joke and the rules change frequently!

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Jade Santiago

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This is such a common confusion point for small business owners! I went through the exact same thing when I first started offering health benefits. The key thing to remember is that even though your employees are paying their portion with pretax dollars, you as the employer are still the one writing the check to the insurance company for the full premium amount. Think of it this way - you pay $1000/month to the insurance company, then your employee reimburses you $500 through payroll deductions. That $500 they're paying pretax just means it doesn't count as taxable income to them, but you still had to pay the full $1000 upfront. So yes, you get to deduct the entire $1000 as a business expense. The IRS sees this as two separate transactions: 1) You paying a legitimate business expense for employee health coverage, and 2) Your employees contributing to that cost through a salary reduction arrangement. Both are perfectly legitimate and don't constitute "double dipping" - it's exactly how the system is designed to work to encourage employers to offer health benefits!

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Liam Mendez

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This is exactly the explanation I needed! I've been stressing about this for weeks thinking I was doing something wrong with my bookkeeping. Your breakdown of the two separate transactions makes perfect sense - I pay the full amount to the insurer (legitimate business expense) and then get reimbursed by employees through their pretax contributions (salary reduction). I feel so much better knowing this is all above board and actually working as intended. Thanks for taking the time to explain it so clearly!

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