Strategy Summary

How can I get a tax deduction for my health insurance?

If you’re a small business owner or sole proprietor, you’ve probably wrestled with how to deduct your health insurance premiums and medical expenses from your taxes. Do you purchase through your business and try to “expense it”? What about a self-employed deduction? And if you have employees—how can I reimburse them without triggering tax consequences?

This guide is designed to help small business owners and sole proprietors discover and implement the most tax-efficient strategy for health insurance and medical expenses.

In this guide, we suggest the most tax-efficient strategies for small employers to pursue when purchasing health insurance so that they can maximize their tax deductions. A quick disclaimer—we’re licensed health insurance professionals and small business insurance experts, not tax professionals. Although we share our experience and advice and do our best to cite authoritative sources, you should always seek professional tax advice and not construe anything in this guide as specific tax advice because every situation is different. Ok? Good.

Let’s jump right to it—your best tax strategy will depend on three things:

  1. Your business entity type
  2. Whether you work alone or have (or plan to have) W-2 employees
  3. Whether you’re an owner or an employee

Based on the above, here is a quick table to summarize our recommendations (download a PDF version). The rest of this guide will explain these strategies in more detail. Please be sure to consult with a tax professional before implementing any of these strategies yourself:

Small Business HRA Tax Strategy Overview
Figure 1: Small Business HRA tax strategy overview by business entity type. Download a PDF version of this chart. Not to be used for tax advice. Please consult with a tax professional before implementing any strategy.

This is a bit of a “choose your own adventure” guide, so if you want to skip to the section that applies most directly to you, please feel free to do so. Here’s what we’ll cover:

Update: In October 2018, two new types of HRAs were announced (the “Excepted Benefit HRA” and the “Individual Integrated HRA”) that will be available starting in 2020. We’re very excited about them but they are not available yet. We will update this guide once their rules are finalized and we get closer to 2020 when they can be legally implemented.

Should I reimburse or try to get a group health plan?

Reimbursement vs Group Health Plans

We have many clients that initially reach out to us asking how they can get a group health plan for their family or 5-person small business. It used to be that binding a few folks together to “get on the group plan” was the only way to purchase insurance.

This notion is reasonable but is no longer true and can be a harmful strategy. Here’s why: with the passage of the Affordable Care Act (ACA) the individual insurance market and the small group market (for employers with 50 or fewer employees) now share the same actuarial tables. Actuary tables are the fancy calculations insurance companies and regulators use to set rates. This means there’s no real savings to be found on the group market compared to the individual market. Instead, you end up locking employees into a “one-size-fits-all” group plan, when they likely would have been able to optimize better by choosing their own plans.

The one exception to this is in some markets insurers will offer different types of plans on the individual and small group markets. For example, it’s not uncommon for an insurance company to only offer a PPO plan in the group market and not to individuals. If that’s the case where you live and you have to have a PPO, then going to the small group market may make sense, but it’ll be very expensive.

Tax Deductions vs Business Expenses: What’s the difference again?

In case you’re not an IRS agent or a tax nerd, let’s quickly talk about the difference between taking a personal, self-employed deduction versus a Business Deduction on a Schedule C. It’s helpful to visualize the “tax waterfall” of how your business profits and losses trickle down from your business to your self-employment taxes and ultimately to your personal income taxes. Here’s a chart to help explain:

small business hra small business tax waterfall

Let’s walk through this briefly. Your business income and expenses are recorded on Schedule C and used to calculate your Net Profit (or Net Loss) from your business activity. Your profit (we’ll assume a profit for these examples) is then reported on your Schedule SE (line 2) to calculate the amount of self-employment tax you owe as well as your self-employment deductions. On your Personal Tax Form, you start with your business profit (Line 12) from Schedule C, subtract deductions calculated on your Schedule SE to get your Adjusted Gross Income (AGI), and finally elect either the standard or itemized deduction method to reach your Taxable Income (Line 43). The higher up the waterfall you can deduct your health insurance and medical expenses the greater the impact those deductions will have downstream when you calculate what you owe in taxes.

Let’s share a quick example: Bob, Sally, and Frank each own separate businesses. At the end of the year, all three had business income of $200k and expenses of $100k for a net profit of $100k. Let’s also assume all three paid $15k that year for health insurance premiums and had $5k in medical expenses.

  • No Deductions: Bob is not a good record-keeper when it comes to health stuff. At tax-time, he records $100k in business profits. We can estimate Bob’s self-employment tax to be about 15%, or $15k in this scenario. On his personal income form, he deducts a portion of his self-employment taxes and then takes the standard deduction. His taxable income comes out to about $80k. At a personal tax rate of about 15%, that means he owes $12k in income taxes. Bob pays $27k ($15k self-employment taxes plus $12k income taxes) in taxes and goes about his day because he doesn’t know any better.

  • Tax Deductions: Sally has done a good job keeping track of her medical expenses and receipts. Like Bob, she reports a $100k business profit and calculates her self-employment tax to be about $15k (we’re using 15% to estimate again). On her personal tax form, Sally records the amount she paid in insurance premiums ($15k) on Line 29 to take the Self-Employed health insurance deduction in addition to the standard deduction. This reduces her taxable income to $65k, meaning her income tax burden is about $9,800 if we estimate it at 15%. Sally’s total tax bill is $24,800. She saves over $2,200 in taxes compared to Bob!

  • Business Expense: Now, Frank has this whole thing really figured out. While his business also made $200k in income and had $100k in operating expenses, Frank was able to include both his insurance premiums and medical expenses as a business expense, so his business profit is only recorded at $80k. Frank calculates his self-employment tax to be about $11k. On his personal taxes, he can’t take the self-employed deduction, but his income is only recorded as $80k and he takes the standard deductions to get his taxable income down to about $60k. At the same 15% income tax rate we’ve been assuming, Frank’s income tax due would be about $9k. Frank’s total tax bill is $20k. He’s saved $4,800 more than Sally and $7,000 more than Bob!

To summarize, despite having businesses with similar revenues and operating expenses, how and where you’re able to record your health insurance and medical expenses makes a big difference in the taxes owed for Bob, Sally, and Frank:

  Bob
(No Deductions)
Sally
(Tax Deductions)
Frank
(Business Expenses)
Business Revenue $200,000 $200,000 $200,000
Business Operating Expenses $100,000 $100,000 $100,000
Business Health Expenses $0 $0 $20,000
Reported Business Profit $100,000 $100,000 $80,000
Self-Employment Taxes $15,000 $15,000 $11,000
Self-Employment Health Insurance Deductions $0 $15,000 $0
Taxable Income $80,000 $65,000 $60,000
Total Taxes Owed $27,000 $24,800 $20,000
Table 1: Illustration of Tax Consequences of not deducting healthcare expenses, taking the self-employed deduction, and taking a business expense deduction. Not intended to be tax advice. Please consult with your tax professional.

This simple example illustrates a key point—your goal as a business owner is to get as much of your and your employees’ medical expenses counted as a business expense as legally possible. At the very least, you should keep records so you can take a deduction. As you can imagine, the tax implications only grow as your business grows.

Your goal is to get as much of your and your employees’ medical expenses counted as a business expense as legally possible.

Ok, so how do you do it? We want to introduce you to your best option—the Health Reimbursement Arrangement or “HRA”. You may have guessed this was coming by the title of this guide. HRAs have an interesting history and come in a few different flavors. Understanding how they work is essential to making your health insurance dollars as tax-efficient as possible.

In the next section, we’ll talk about the types of HRAs and then share how we would use each strategy based on your business and ownership structure.

Why do I need an HRA? Can’t I just reimburse and “expense it”?

Before we get further into HRAs, we should address this commonly asked question. It feels like just reimbursing for insurance or scribbling it in on your taxes as an expense would make sense and be a practical solution, but unfortunately the answer is a clear “NO”—you cannot reimburse yourself or employees and expense it from your business (even if you’re a sole proprietor). We meet a lot of business owners who were casually reimbursing for healthcare expenses and got hit with big IRS fines.

Reimbursing health insurance or medical expenses is not like reimbursing for a bus ticket or office supplies. The reason is the IRS treats reimbursements for health insurance and medical expenses like a salary payment to employees (IRS Notice 2013-54). Salaries require payroll taxes to be withheld by employers and income tax to be paid by employees. Don’t get between the IRS and their tax money. It doesn’t end well.

It gets worse. Under the Affordable Care Act (ACA), your reimbursements actually constitute a group health plan called an Employer Payment Plan (EPP)—albeit a non-compliant one. The penalty is $100 per employee per day, according to the IRS. Yeesh. Not worth the risk.

Ok, let’s talk about HRAs now!

Overview of HRAs

Types of HRAs

HRA stands for “Health Reimbursement Arrangement”. They are not overly complicated or scary but are built on a series of regulations to make sure they are being offered fairly and are achieving their intended aim of helping employees pay for benefits tax-free. The regulations also try to prevent the reimbursements from being used for things like executive compensation, fraud, discrimination, money laundering, etc.

The regulations that have historically (and still) govern traditional HRAs come from Tax Code Section 105. Because of this you’ll hear tax geeks and insurance brokers refer to “Section 105 HRAs”.

You’ll also hear people talk about Integrated HRAs and Standalone HRAs. Here’s the difference:

  • Integrated HRAs are “integrated” with a traditional group health insurance plan and used to help reimburse out-of-pocket medical expenses not paid for by the group health plan. Typical examples would be co-pays, co-insurance, deductible payments, etc.

  • Standalone HRAs are not required to be tied to a group plan. They have a complicated history and can be even more complicated to implement based on tangled federal and state insurance regulations. A few common types that still linger around are:
    • Spousal HRA—For employees covered by a spouse’s group plan, a Spousal HRA could reimburse medical expenses but not premiums.

    • Retiree HRA—For former employees of a firm, an employer could use a Retiree HRA to help pay for retired members’ insurance premiums and medical expenses.

    • Medicare HRA—For employers with less than 19 employees, employers could elect to reimburse a portion of an employee’s Medicare supplement premiums.

We want you to know about these different types of HRAs in case you’re talking to an old-school insurance broker or searching around the internet and come across old articles that mention some of the above HRA types (and in this case, old means before 2017).

It’s also important to know that in 2017 we got a new HRA, a special type of standalone HRA for small employers called a QSEHRA. QSEHRA stands for “Qualified Small Employer Health Reimbursement Arrangement”. The major difference is that QSEHRA was created through federal law (The 21st Century Cures Act) and not just conjured out of regulations. This makes QSEHRA much easier to understand and implement nationwide. It’s also super flexible, as we’ll talk about later. For this reason, we believe QSEHRA supersedes the previously described Standalone HRAs in 99% of situations.

Jack

Pro-Tip: Because of its legal footing, we believe QSEHRA effectively replaces previous standalone HRA implementations for small business owners and sole proprietors.

HRAs we recommend for Small Businesses and Sole Proprietors

Since this guide is about helping small business owners and sole proprietors implement an efficient tax-strategy, rather than talk about all HRA combinations in depth, we’re going to focus on the two we believe are most powerful and most relevant for owners and proprietors today:

  1. One-Person 105 HRAs: These are traditional HRAs integrated with an individual or family health plan

  2. QSEHRAs: These are the new standalone HRAs that allow small employers to reimburse employees for individual insurance and medical expenses

These HRAs are the best pathway for small business owners and sole proprietors to count their health insurance and medical costs as business expenses at the top of the tax waterfall. We provide a high-level summary of these HRAs below and then talk about strategies to deploy them based on your business entity type.

Note: In 2020 we’ll be able to recommend two new types of HRAs, the “Excepted Benefit HRA” and the “Individual Integrated HRA”. These HRAs were proposed in October 2018 and are still bouncing around the regulatory offices. As soon as we have more information on them, we’ll add them to this analysis. Until then, the two types of HRAs above are your best bet.

One-Person 105 HRA

A One-Person 105 HRA goes by several names out in the wild. You may also see it called a “Single Participant HRA”, a “Section 105 HRA”, or a “One-person HRA”. This is because it doesn’t really have a name. It’s just a thing born out of a weird (but tried and true) loop-hole in Section 105 of the Tax Code under the Self-Insured Medical Reimbursement Plan provisions. For simplicity going forward, we’ll refer to them as “One-Person 105 HRAs”.

Recall from our overview of HRAs above that Section 105 HRAs must be integrated with a group health insurance plan. Group health regulations and IRS rules also specify that the HRA must be offered fairly to all eligible employees. But what if you only have a group of 1? Aha!

The question that lingered for years was if your business has only one employee (even if that employee happens to be you the owner), could that employee purchase an individual health insurance plan and integrate it with an HRA to get the benefits described in Section 105?

Thankfully the answer is “yes”, as long as you can meet the non-discrimination restrictions (IRC Section 105(h)(3)). In most cases, the only way to meet those restrictions is just to have one eligible employee; hence why we are calling this a “One-Person 105 HRA”. Essentially, you’re operating a regular HRA for a group of one. If you were to ever hire another eligible employee, the HRA would fail under Section 105 because that employee does not have access to participate in your individual or family health plan.

Jack

Pro-Tip: You can keep a One-Person 105 HRA and hire other employees if they fall into a category that can safely be deemed “not eligible” for the HRA in the eyes of the IRS. This includes employees under the age of 25, part-time employees (less than 25 hours a week), seasonal employees (less than 7 months a year), or employees with fewer than 3 years of service. Make sure to talk this through with your accountant and attorney. See IRC Section 105(h)(3); Reg. Section 1.105-11(c)(2)(iii)(C).

The One-Person 105 HRA will work great if you’re an owner and you’re the only employee of your business. If your business is structured as a corporation, this is easy. If you’re a sole proprietor, this is tricky because owners are not employees in the eyes of the IRS. There’s a work-around we’ll talk about in the Proprietor Strategy section below where you can hire your spouse as an employee to make it work.

So, why have a One-Person 105 HRA? What are the benefits?

  • Turns a tax deduction on your personal taxes (Form 1040) into a business deduction (Schedule C), reducing business and self-employment taxes
  • Makes what you spend on health insurance premiums and medical expenses (copays, coinsurance, dental, etc.) into a business expense, as opposed to the self-employed deduction, which only allows you to deduct premiums
  • Has ability to create a Net Operating Loss (NOL) deduction (for future years), which is not possible with the self-employed deduction even if you lose money
  • Creates a full deduction for long-term care insurance and prescribed Over-the-Counter (OTC) drugs
  • Not subject to the annual reimbursement limits of the QSEHRA
Jack

Pro-Tip: If you’re the only employee of your business and you have very high medical expenses, you should consider reforming your business as a C-Corp. Yes, you’ll be subject to double-taxation, but all your medical costs can become business expenses, greatly reducing your tax liability. Make sure to talk to your accountant!

Small Business HRA (QSEHRA)

QSEHRA stands for “Qualified Small Employer Health Reimbursement Arrangement”. It is sometimes called a Small Business HRA. We like to call it just QSHERA (“Q-Sarah”). We love QSEHRA so much we created an entire online guide like this one to unpack its nuances and discuss design strategies and implementation. If QSEHRA is an effective strategy for you or your employees, then I recommend you skim through our practical QSEHRA guide for small employers.

In summary, QSEHRA allows small employers with fewer than 50 full-time employees to reimburse employees tax-free for individual insurance premiums and medical expenses. This is awesome, because it allows every dollar you spend to help your employees with insurance and medical expenses to be categorized as a business expense. If you’re giving employees a health insurance stipend or “bonus” or adding to their salaries to help with insurance, you’re a nice boss but you’re being like Bob in our example above and triggering taxes that you can avoid for both your business (payroll taxes) and for your employees (income taxes) could be avoiding. Here’s a tax calculator you can use to see for yourself.

QSEHRA is based on a reimbursement model. You the employer set the amounts you want to allow for reimbursement, and employees make claims to get paid. Reimbursements are subject to annual limits that are tied to inflation. As of 2018, the limits are $5,050 a year ($420/mo) for single employees and up to $10,250 a year ($854 a month) for employees with families. These limits are usually great for employees but can feel restrictive if you, the employer, are the only employee and you have high insurance or medical expenses you’d like to include as a business expense.

Like One-Person 105 HRAs, QSEHRA works great if you’re an employee of your company. This can be tricky if you’re a sole proprietor or pass-through entity. We’ll talk about some strategies for those types of entities in the following sections.

What are the benefits of QSEHRA?

  • Turns everything you spend on employee health benefits (including your own if you’re also an employee of your business) into a business expense (Schedule C)
  • Allows employers to control costs and set the maximum reimbursement limits allowable
  • Gives employers a lot of flexibility to set reimbursement rates, choose eligibility, and select what they want to reimburse or not
  • Gives employees ability to choose what they want as long as they meet the insurance requirements for Minimum Essential Coverage (MEC) and the guidelines that you create
  • Provides an optimized approach to group benefits instead of a “one-size-fits-all” traditional group plan
Jack

Pro-Tip: Setting up and managing a QSEHRA does not have to cost a lot or add complication to your business. Check out our QSEHRA Administration service. Our fees are nominal compared to your potential tax savings.

Corporations

What’s the best tax strategy for health insurance if I’m a corporation?

Corporations are the easiest entity type to handle when it comes to health insurance because owners can also be employees. If you’re just getting started, there are obviously other implications with corporations you should talk to your accountant or attorney about.

Corporations for this discussion include C-Corps, B-Corps, Non-Profits, and LLCs taxed as C-Corps—anything where the entity is separate from ownership. As a corporation, you should be able to get all your insurance premiums and medical expenses counted as a business expense (Schedule C).

Here’s how we suggest Corporations approach health insurance (please consult your tax professional):

Small Business HRA Tax Strategy for Corporations
Figure 2: Suggested tax strategies for Corporations to maximize healthcare deductions. Download a PDF version of this chart. Not to be used as tax advice. Please consult with your licensed tax professional before implementing any strategy. 

Your best strategy will hinge on whether you are the only employee and have no plans to hire in the future or if you have (or plan to soon hire new) W-2 employees. If you are the only employee of the corporation, you can choose between a One-Person 105 HRA or a QSEHRA. We’d recommend:

  • If the QSEHRA’s reimbursement limits are enough for you, we recommend going with QSEHRA because it’s much cleaner regulatory-wise (see our HRA Overview section above) and you’re less likely to run into any reporting hurdles.
  • If you have high insurance or medical expenses, then you need to go the One-Person 105 HRA route. This is because there are no statutory limits to how much you can expense through your business.

Depending on which strategy makes the most sense for you, please see our Next Steps section below and we can point you towards some resources to get started.

Proprietorships

What’s the best tax strategy for health insurance if I’m a sole proprietor?

Sole Proprietorships are awesome because, well, you’re doing your own thing! It can get a little tricky though because there’s no separation between you and your business in the eyes of the IRS (i.e., you’re a “pass-through entity” or “disregard entity”) and owners are generally not considered to be employees even if you’re working for your company full-time. This includes Sole Proprietorships and Single-Member LLCs that did not elect corporate taxation.

Here’s what we suggest for Sole Proprietors (please consult with your tax professional):

Small Business HRA Tax Strategy for Sole Proprietors
Figure 3: Suggested tax strategies for Sole Proprietors to maximize healthcare deductions. Download a PDF version of this chart. Not to be used as tax advice. Please consult with your licensed tax professional before implementing any strategy. 

The best strategy for you depends on whether you have W-2 employees and your marital status (bet you didn’t expect that—we’ll explain). If you’re single and work by yourself, or if you have W-2 employees or plan to hire soon, your best course of action is going to be to take the self-employed deduction for yourself and set up a QSEHRA for your W-2 employees. That will get all your employees’ expenses into the business expense category. Unfortunately, you can’t get your personal insurance and medical expenses categorized that way, but we can still save some tax money by getting all your self-employed deductions. Skip to our Next Steps section to see how.

If you are a sole proprietor and work for yourself and have no plans to hire, and you are married, then we can explore a few more options. Recall from our HRA Overview section that HRAs only work for employees. Although as a proprietor you generally are not eligible for an HRA because you’re not an employee, your spouse can be an employee and eligible for an HRA and health plan that covers you.

Here’s the strategy if you’re a sole proprietor with no employees and you’re married:

  • Hire your spouse as a W-2 employee:
    • Your spouse’s salary can just be the amount you want to reimburse through the HRA, but it must be a fair wage for what they are doing (i.e., you can’t reimburse $100k through an HRA if your spouse is not actually doing that much work)
    • It’s a good idea to have an employment contract and timesheet for record-keeping purposes

  • Make your spouse the primary member on your family health plan

  • Cover yourself as a dependent on your spouse’s health plan

  • Set up a One-Person 105 HRA or QSEHRA for your spouse:
    • Choose QSEHRA if you have health expenses that are less than the QSEHRA reimbursement limit ($10,250 as of 2018) or have other employees that are excludable under the QSEHRA regulations so that your spouse is the only eligible employee for the QSEHRA (see the Reimbursement Rules section of our QSEHRA Guide)
    • Choose the One-Person 105 option if you have significant medical expenses or have other employees that are only excludable under the One-Person 105 rules (see Pro-Tip in the One-Person 105 HRA section above); the One-Person 105 HRA meets the HRA discrimination requirements because your spouse is the only eligible employee

  • Save all your medical bills and records and have your company reimburse the bills each month from a separate account

This strategy only works if you don’t hire any other W-2 employees that would be eligible for either the QSEHRA or One-Person 105 HRA (make sure to look at those rules closely) and assumes that you and your spouse don’t own any other businesses that have employees (common ownership rules would likely apply and the plan would fail to meet Section 105 requirements). You’ll need to keep good records, too. This sounds like a loop-hole and it is, but it’s held up in tax court. The main case was Shellito v. Commissioner. If the above applies, see the Next Steps section for how to get started!

Jack

Pro-Tip: We’ve heard of anchor-spouses for immigration purposes, but we don’t recommend anchor-spouses solely for health insurance tax strategies. Make sure you love them first :)

Partnerships & S-Corps

What’s the best tax strategy for health insurance if I’m a Partnership or S-Corporation?

If you’re not a corporation and you’re not a proprietor, you fall into this last category we collectively refer to as “Other Pass-Through Entities.” Like proprietors, these are entities where income from your business “passes through” and is reported on your personal tax form. Most of the time, you’re not able to classify yourself as an employee (even if you work for your business full-time) and instead are classified as an owner and required to pay self-employment taxes (talk to your accountant). These entities are typically S-Corps, Partnerships, and LLCs taxed as S-Corps or Partnerships. Note, when we talk about owners of S-Corps, we’re talking about owners with greater than 2% ownership.

Here’s how we suggest Partnerships, S-Corps, and LLCs taxed as such approach health insurance (please consult with your tax professional):

Small Business HRA Tax Strategy for Partnerships and S-Corps
Figure 4: Suggested tax strategies for Partnerships & S-Corporations to maximize healthcare deductions. Download a PDF version of this chart. Not to be used as tax advice. Please consult with your licensed tax professional before implementing any strategy. 

For Partnerships and S-Corps, there’s not a legal way (that we’re aware of) for owners to get their personal insurance and medical expenses counted as a business expense. If you read the Sole Proprietors Strategy section, you might ask, “wait, why can’t I hire my spouse and do what proprietors can do with the One-Person 105 HRA thing?” The problem for S-Corps are that spouses are attributed ownership of the S-Corp. The problem with Partnerships are that there’s more than one person (hence “partnership”) and the One-Person 105 HRA rules fall apart.

Jack

Pro-Tip: If you are a partner in a partnership, your spouse can be hired as a W-2 employee (assuming he or she has no ownership stake in the partnership), and then you can set up the QSEHRA for your spouse and any other W-2 employees.

For Partnership and S-Corp owners, your best bet is to take the Self-Employed Health Insurance Deduction. We explain more how to do that in the Next Steps section below. The good news is that you can still have your business pay for your health insurance premiums. From the IRS Form 1040 Instructions:

  • If you are a partner, the policy can be either in your name or in the name of the partnership. You can either pay the premiums yourself or your partnership can pay them and report them as guaranteed payments. If the policy is in your name and you pay the premiums yourself, the partnership must reimburse you and report the premiums as guaranteed payments.
  • If you are a more-than-2% shareholder in an S corporation, the policy can be either in your name or in the name of the S corporation. You can either pay the premiums yourself or the S corporation can pay them and report them as wages. If the policy is in your name and you pay the premiums yourself, the S corporation must reimburse you. You can deduct the premiums only if the S corporation reports the premiums paid or reimbursed as wages in box 1 of your Form W-2 and you also report the premium payments or reimbursements as wages on Form 1040, line 7.

If you have employees, you’ll want to set up a QSEHRA. Although you won’t be able to participate as an owner, you’ll be able to get all your employees’ eligible expenses recorded as a business expenses (Schedule C), which helps you reduce the self-employment taxes you’ll owe. So still a big win for you and a great benefit for employees! See the Next Step section for getting started.

Next Steps

I need to take the self-employed tax deduction

Great! It’s going to be important that you keep good records. You’ll want to understand what is deductible and what is not. Here’s a good list that can help you.

Jack

Pro-Tip: A good rule-of-thumb when thinking about whether something is deductible as a medical expense is to ask if something is medically necessary or just recommended? Doctor visits and prescriptions are typically necessary and therefore deductible while cosmetic surgery is usually not.

Note that there are two places you can take deductions on your personal taxes (Form 1040):

  1. The Self-Employed Deduction (Line 29)
  2. If you itemize your expenses (Line 40)

For the Self-Employed Deduction, it’s pretty straightforward, and the IRS provides a pretty good worksheet in the Form 1040 instructions for Line 29 so we won’t cover that here.

If you had significant expenses, you may be able to itemize those expenses and take an even larger deduction if your medical expenses were greater than 7.5% of your Adjusted Gross Income (AGI) in 2017 or 2018. This limit is expected to go up to 10% in 2019 and beyond. You should save good records and consult a tax professional or use tax preparation software to take the itemized deduction.

If you’re an S-Corp owner (more than 2% ownership) or partner in a Partnership and your company is paying for or reimbursing you for your health insurance premiums, make sure to follow the instructions discussed in the Partnerships & S-Corps section for reporting these reimbursements as on your W-2 or as guaranteed payments.

I need to set up a One-Person 105 HRA

Cool! The first thing you’re going to need are your legal plan documents. These are an absolute requirement. You can’t just start operating and reimbursing like a One-Person 105 HRA without having the proper documentation, but the documents don’t need to be expensive. You’ll want to talk to your attorney or accountant to see if they have any document templates available. We recommend HRAPlanDocs.com for One-Person 105 HRAs (what they call "Single Participant HRAs").

Next, you will need to come up with a receipt management system. Since it’s “all in the family”, privacy isn’t as big a concern as it is with QSEHRA, but you’ll want to get organized.

I need to set up a QSEHRA

Awesome! Similar to the One-Person 105 HRA, you’ll need legal plan documents, employee notices, and a system to substantiate employee claims without violating their privacy.

You’ll want to check out 3rd party services to help here. At Take Command Health, we’ve designed an online QSEHRA Administration service specifically for small employers. We’ll help you design your plan and create your plan documents. We have a low monthly subscription fee to manage employee receipts, create reimbursement reports, manage compliance, and help with year-end reporting. Employees can make claims by taking photos with their smart phones, so it’s pretty easy. We can also help employees find a health plan that covers their doctors and prescriptions if they need help.

Yes, we do have other competitors, but we hope if you have found this guide helpful, you’ll consider us. At the very least, we’re happy to talk with you and answer any QSEHRA questions you may have.

Jack

About the Author: Hi, I'm Jack and I wrote this guide to help you make the most of your QSEHRA reimbursements. I had a lot of help from my team and our attorney too!

As a licensed health professional and leading QSEHRA expert, I've been published in the New York Times, Wall Street Journal, Forbes, and others on helping small employers realize the potential of QSEHRA. I am a small business owner and have an MBA from Wharton.

If you have any questions, please chat with me or my team or fill out the form below. Thanks for reading!