Employee Benefits: Insurance

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The following is a chapter from Employee Benefits: How to Make the Most of Your Stock, Insurance, Retirement, and Executive Benefits by Josh Mungavin CFP®, CRC® and Edited by Chris Boren & Tristan Whittingham.




Health Insurance Options

Health insurance options change every year, so it’s important to look over new healthcare options every year. Think about how these options are presented to you, think of everything that will affect you and your family, and reanalyze the math you did the year before to make sure the plan you’re in, if still available, is the right plan rather than just staying in a plan that may no longer be right for you. You have to look beyond the premium. While a low-cost plan might be nice if you don’t expect anything to happen, remember that everyone is healthy until they’re not.

Optimal Use: Strategies and Analysis

You must look at copays (i.e., the fixed amount you pay for services), deductibles (i.e., the amount you pay before your insurance starts paying), coinsurance (i.e., the percentage of costs covered after you meet the deductible), and out-of-pocket maximums (i.e., the most you’ll have to pay before the insurance pays 100% of any remaining costs). Depending on your health that year, going with a lower premium might end up meaning you need to pay higher out-of-pocket expenses. Things to think about include new babies, newly diagnosed illnesses, or a recent marriage. You also want to know if you have dental and vision coverage and how long it has been since you’ve used either. It’s also important to look over which health plan will be most beneficial to you over the year and not let the “tax tail wag the dog” by looking at the tax and savings benefits of a Health Savings Account (HSA) and whether a plan without a high deductible will be more beneficial for you over the course of the year since taxes aren’t everything (HSAs are discussed in more detail in the next section).

Generally, plans cover preventative care such as annual physicals, gynecologist visits, mammograms, and immunizations at no cost, but that varies from plan to plan. Make sure that you can use the doctors you want to go to under the plan you choose and that you’re not limited to a doctor who works for an insurance company you may or may not be happy with when you already have an existing physician.

One way to compare a traditional healthcare plan and a high-deductible plan is as follows: take the annual premium, deductible, coinsurance after the deductible, out-of-pocket limit, any employer contributions to the HSA, and the tax break you get from the HSA to do a little math. The math works as follows: look at the cost of coverage if you need absolutely nothing over the course of the year. To do that for the traditional plan, use the annual premium as the total cost. To do that for the high-deductible plan, use the annual premium minus the tax benefit of fully maximizing the HSA plan if you plan to fully do so or the tax benefit of any amount contributed to the HSA plan.

17. Traditional plan Annual premium Total costSo, if the annual premium for the traditional plan is $1,000 a month, its yearly cost to you is $12,000 if you don’t need any medical care at all.

18. Traditional plan Annual Premium 1000 monthIn this case, if the high-deductible plan costs $500 per month, the yearly cost is $6,000 minus the tax benefit of the HSA deduction.

19. High-deductible plan Annual premium 500 monthIf you maximize the HSA as a family with the full $6,900 per year allowed and you are in the 20% tax bracket you get a tax benefit of $1,380 (Note that your personal tax rate makes a big difference, so one person’s decision may be completely different than another’s given the same circumstances and the same plan but different tax rates). From there, take the yearly cost of a high-deductible plan coverage of $6,000 and subtract the tax benefit of $1,380 for a total yearly cost of $4,620.

20. Maximizing the HSA as a family

If you do not need any medical care, subtract any employer HSA contributions for the year from your effective yearly number (for this example, we’ll use no money from the employer so the calculation is easy). The high-deductible plan coupled with the HSA also allows the benefit of tax-free growth on the investment of $6,900, which is a benefit you would see above and beyond the effective yearly premiums, being $7,380 less expensive (calculated as $12,000 traditional plan annual cost – $4,620 HDHP annual cost after adjusting for the HSA tax benefit, all as illustrated above).

Next, we’ll look at how much the plans would cost if you maxed out your coverage for the year. In this case, let’s say the traditional plan has an out-of-pocket maximum of $3,000 and the high-deductible plan has an out-of-pocket maximum of $10,000.

21. Traditional plan Out of Pocket maximum 3000For the traditional plan, add the $3,000 out-of-pocket maximum to the $12,000 yearly cost of premiums for a total insurance cost of $15,000 as a worst-case scenario.

22. 12000 premium yearly cost

For the high-deductible plan, add the $4,620 “effective” premium to the $10,000 out-of-pocket maximum for a worst-case scenario of $14,620.

23. 4260 Premium yearl costIn this case, taking the high-deductible plan would be something of a no-brainer. The math changes substantially if the cost for the yearly premium under the traditional plan is only $7,000. In this case, the worst-case scenario would be the $7,000 yearly premium plus the $3,000 maximum out-of-pocket for a total worst-case scenario of $10,000.

24. Traditional plan Yearly Premium 7000

You would then compare the traditional plan’s worst-case scenario of $10,000 to the high-deductible plan’s worst-case scenario of $14,620 to see a difference of $4,620 dollars in a worst-case scenario per year.

25. 14260 High deductible worst case

Now look at the difference between the $7,000 traditional yearly premium and the $4,620 effective high-deductible yearly premium, and you’ll come up with a difference of $2,380 per year of an effective premium difference.

26. 7000 Traditional yearly premium

Now you will calculate the number of years it will take you to break even by dividing the $4,620 difference in a worst-case scenario by the $2,380 per-year effective premium difference to come up with 1.9 years to break even.

27. 4260 Difference in worst case scenario

This means that as long as you don’t max out your insurance every other year, you are better off with a high-deductible healthcare plan even though you will max out the high-deductible healthcare plan in some years, making you worse off for that year. In this case, you will have saved money over the long run by going with the high-deductible healthcare plan as long as you can afford to pay for your medical costs in the years with high expenses. If you find that the break-even point is three, four, or five years, it may be worthwhile to look more closely at the traditional plan. If you expect to have regular healthcare treatment needs or plan to have some level of expenses every year, you may need to alter this calculation so the 1.9 years to break even becomes a little bit longer since you will have to pay everything out of pocket using the high-deductible healthcare plan, whereas you may have some help paying in the years with a moderate amount of healthcare costs with a traditional healthcare plan.

Generally, a high-deductible healthcare plan with an HSA will be more attractive to younger people in good health who aren’t expecting to have any children or major medical issues. The good news here is that if you make the wrong decision, it’s only the wrong decision for one year and you’re not locked in forever since you can move to the other plan at the end of the year. Furthermore, if you have any money in an HSA, you can keep that and use the HSA money whether you decide to use the high-deductible healthcare plan or a traditional healthcare plan the next year.

It’s important when working through a health insurance analysis to look over the health insurance options available through your spouse or domestic partner’s employer (if the employer covers domestic partners) to make sure you choose the best plans since you may want to split coverage or have both of you covered under one of the plans.

General Considerations

Will you have access to a flexible spending account (FSA) or an HSA? Both options allow you to set aside pre-tax dollars to cover future medical expenses, but there are differences between the two.

If you have the option of setting up an FSA with your insurance company, do so. Doing this allows you to use the money in the account for copays; however, remember that those funds are use-it-or-lose-it, so make sure you have a back-up plan for how to spend the money by the end of the year, such as new glasses or dental work.

Keep in mind that while HSA savings amounts are federally tax deductible, they may not be deductible for state tax purposes depending on what state you live in.

Health Savings Accounts

According to a 2018 study, the average couple who is 65 years old today will require an estimated $280,000 in today’s dollars for medical expenses in retirement, excluding long-term care.9 It is likely that the amount needed for those who are younger will be even higher. This is one reason, but not the only one, to fully fund an HSA every year in which you are eligible. In fact, I think an HSA is one of the most powerful savings tools currently available, especially if it is used optimally.

Specifically, an HSA is a tax-advantaged account created for individuals covered under high-deductible health plans (HDHP) to save for medical expenses those plans do not cover.10

Optimal Use of an HSA

In 2017, only 18% of the money that went into HSA accounts stayed invested until the end of the year. This means most people use HSA money to pay off current bills. Putting only enough money in an HSA to cover your current year’s medical bills is a straightforward way to get a tax break for your non-deductible medical bills for the year, but I think there’s a better way.11

A large portion of the long-term benefits of an HSA comes from the tax-free growth of the account through the years. This means that the longer you invest in the HSA, the higher your likely lifetime benefit. To get the most value from the HSA investment vehicle, fund the HSA with the most you can every year but hold off on using the funds (absent an emergency) until late in life. Retirement healthcare expenses should be one of the first uses of HSA funds. In addition to regular out-of-pocket medical expenses, you can generally use HSA funds to pay for premiums for long-term care (with the qualifying amount based on age), health insurance continuation coverage (i.e., COBRA), health insurance while receiving unemployment, and Medicare if you’re over age 65 (not including Medigap).

Receipts for medical expenses that were not deducted through the years should be saved along the way. There is currently no deadline for self-reimbursements, so if you have paid out of pocket, have not deducted the expense on your taxes, and have the records, you can theoretically reimburse yourself for years’ worth of expenses if you need extra money and do not have anywhere else to withdraw from or if you have more money in your HSA than you will need for lifetime health expenses.

Furthermore, if you find yourself with sufficient funds to fully reimburse yourself for all past medical expenses and cover all future medical costs, you can consider taking distributions from the HSA for living expenses. While HSAs do not have any minimum distributions after age 70.5 like IRAs, you do have the option to use the funds for anything, paying only taxes with penalties after age 65.

If the HSA account is severely overfunded and there is charitable intent, this may be the first account to turn to for charitable bequests by naming the charity of your choice as the beneficiary of your HSA. Otherwise, you may think about intentionally beginning to draw the account down slowly so taxes are spread out over the course of years. Unlike retirement accounts, HSA accounts are liquidated upon the death of the account owner, and all taxes are due as ordinary income in the year of death. Meaning, a highly funded HSA could push you into a much higher tax bracket than normal.

Finally, remember that we are always subject to changes in tax law when you are planning a very long-term tax and investment strategy (as we plan the government laughs).

HSA Providers and Account Costs

There are quite a few HSA providers, but the expense breakdown usually follows a similar formula. The HSA provider has a banking side and an investment side. There is a $2.50 per-month fee if the banking side doesn’t maintain a balance over $5,000. This fee amounts to 0.6% of the $5,000, which I believe the investments will outperform over time. This means, it makes sense to pay the fee rather than keep the cash on the bank account side. There is also the underlying investment fund fee, which can be minimized by using the link to a brokerage firm (if the HSA provider has one) to invest in a much wider variety of funds available than under their standard list of investment options. This allows the account to be linked to an Evensky & Katz portfolio to make the most of tax-sheltering assets that would otherwise create a high percentage of tax liability in the portfolio. There would also be a $3 per-month fee if your investment account drops below $5,000, along with any number of fees attributable to things such as closing the account closure, ordering a checkbook, ordering a debit card, and so on.

It’s crucial to know how you plan on using the HSA account and make sure you have the best supplier for your needs based on fees and investment options.

Special Considerations

If the spouse is the beneficiary of the HSA, it will be treated as the spouse’s HSA after your death. If the spouse isn’t the beneficiary, however, the account stops being an HSA, and the fair market value minus any qualified medical expenses for the person who passed that are paid by the beneficiary within one year after the date of death become taxable to the beneficiary in the year in which the account owner dies.

One HSA rollover is allowed per year within 60 days of receipt, but the rollover is not limited in terms of the amount of money rolled over.12 This means you can briefly tap into HSA funds in an emergency as long as you can pay it back within 60 days. Any amount not rolled back into an HSA account will be taxed, and penalties could be charged.

If employers offer HSA funding through a cafeteria plan payroll deduction, it is generally not subject to FICA taxes that go to Social Security and Medicare, which generally amount to about 7.65% of the amount contributed by payroll deduction. This means that absent a better use of your employer cafeteria deduction amount, it can be even more profitable than usual to fund your HSA plan with as much of the cafeteria plan funds as possible.

A qualified HSA funding distribution from an IRA to your HSA can be made once during your life. It reduces the amount you can contribute to the HSA that year by the amount converted. This means, in a year in which you can’t afford to fully fund your HSA from your income and savings, you can fund it with IRA money. If you have saved up sufficient health receipts and you had the HSA open during the proper period, you may be able to reimburse yourself for past expenses with the current value of the account. The money must pass directly from the IRA trustee to the HSA, and it isn’t included in income or deductible. This can be done from a Roth, but that generally wouldn’t make sense since you would be putting money you have already paid taxes on into an account you may have to pay taxes on (if not used for medical expenses). The qualified funding distribution can’t be more than any amount you are entitled to contribute to an HSA that year. You must also remain a qualified individual for 12 months after this transaction takes place, which means your insurance or qualifying insurance must remain in place for 12 months after the money is moved.

This one-time funding of your HSA from your IRA can be beneficial for years in which you can’t fund an HSA, especially if you would otherwise need to tap into your IRA for living expenses (which would cause you to pay taxes and possibly a penalty). Depending on the situation, you may be able to fund the HSA with your IRA funds and then reimburse yourself for past medical expenses from the money now in your HSA, doing away with both the early withdrawal penalty and taxes associated with the withdrawal.

Some HSA Rules

  • HSA distributions prior to age 65 for people who are not disabled for non-healthcare qualified expenses are charged ordinary income tax plus a 20% penalty.
  • An HSA can be funded by an individual, an employer, or a combination of the two. You don’t have to use the employer-provided HSA provider unless your employer requires you to maintain an account with them to receive employer contributions. Once the employer contributions are received, they can generally be transferred to your preferred HSA provider (you can have multiple HSA accounts). Any contributions are tax deductible (even if the tax return does not itemize deductions) but keep in mind that the IRS does not see employer contributions as income, which means they are not taxed to begin with and so cannot be deducted.
  • Funding an HSA requires a high-deductible health plan, and the person for whom the account is titled can’t be claimed as a dependent on someone else’s tax return for the year. In 2018, a high-deductible health plan has a minimum annual in-network deductible of at least $1,350 for an individual or $2,700 for a family and a maximum annual in-network deductible of $6,650 for an individual or $13,300 for a family.13
  • Contributions are limited to a combined funding limit of $3,450 per year for an individual or $6,900 per year for a family in 2018, but remember that the funding levels cover total funding among all HSA accounts, including any Archer MSA accounts. Anyone over the age of 55 can contribute an additional $1,000 per year, which means an individual over 55 can contribute $4,450 and a family with two eligible spouses over 55 years old can contribute $8,900 for 2018.14
  • You (or your family) are eligible for the entire year if you are eligible on the first day of the last month of your tax year (which is December 1st for most taxpayers) even if your spouse has a non-high deductible health plan, as long as the non-HDHP doesn’t cover you. However, there may be some limitations to how much you can contribute, and you may be required to keep the health plan or other qualifying health plan for 12 months to ensure that the HSA contributions are not included in the next year’s income with a penalty.
  • There are other rules to determine eligibility. If you have any questions regarding your eligibility, you should speak with your financial advisor or accountant. Contributions to an HSA can be made until the tax filing deadline for the year, which is usually April 15 of the following year.
  • You do not have to be eligible to save in an HSA account or have a high-deductible healthcare plan to use previously saved HSA money for health expenses tax free. Any money you save in the HSA does not go away at the end of the year. HSA funds roll over and accumulate from year to year (unlike funds in FSAs) and remain in your account if you leave your employer (unlike company-owned Health Reimbursement Accounts).
  • You cannot use HSA money for health expenses that will be reimbursed by your health insurance and still have the HSA distributions count as qualified tax-free distributions. You also can’t deduct medical expenses you have used HSA funds to pay for. You must keep all pertinent records for any HSA distributions, including receipts and proof that the expenses weren’t paid for by a medical plan, reimbursed from another source, or taken as an itemized deduction in any year.
  • Qualified medical expenses are generally expenses your insurance would cover if your deductible had been met that were incurred after you qualified for and established your HSA.
  • You generally can’t use the account to pledge for a loan or buy goods and collectibles without risking the amount used being deemed as distributed for non-qualified medical expenses for the year and fully taxed with potential penalties (although there are some exceptions).
  • Any distributions the HSA owner takes by mistake having reasonably believed they were for a qualifying medical expense can avoid tax consequences by returning the funds to the HSA before April 15th of the year after they discover the mistake.
  • For employers, the amount contributed to employees’ HSAs aren’t generally subject to employment taxes, although there are non-discrimination rules stating that all employees in the same class must receive HSA contributions (if any employees receive HSA contributions) to avoid an excise tax of 35% on contributions. This may mean employers strategically classify full-time and part-time workers, individual and family participants, and employees who are or are not enrolled in high-deductible health plans.

Flexible Spending Account

FSAs allow you to put away money before taxes to pay for medical expenses. You may be able to set aside money every year to use pre-tax dollars for your insurance copays, deductibles, some drugs, and certain other healthcare costs. However, remember that an FSA is a use-it-or-lose-it arrangement, which means you generally must use all or the vast majority of the funds within a certain time frame, generally by the end of the year.

Medical FSAs put all the employee’s annual contributions in at the start of the plan year. The employee can elect to defer a certain amount of money, spend the account down, or leave the employer for another employer without actually saving the amount of money from their paycheck withholdings that they’ve spent on tax-free medical expenses.


If the plan allows the rollover of a certain amount of money, it is almost always recommended to fund the FSA with at least the amount you can roll over from one year to the next to take advantage of the tax savings as long as you have the excess cash flow to afford to do so. Keep in mind that this money may go away if there is a separation from service with your employer, so it can be very important to spend down an FSA before quitting or being terminated from your employer.

If you decide to use an FSA, make sure you know how you’ll spend any extra money at the end of the year, including getting an additional pair of glasses, having dental work you might not otherwise have done, or buying medical equipment you need or know you will need. If you find you are getting close to the end of your plan year and you have money left in the plan you will not spend, it is worthwhile to go on websites that cater to FSAs to see what you may need that is available rather than losing the money when the plan year ends.

Remember that there may also be requirements to apply for refunds or reimbursements from the plan, so the dates of those filings should be noted and followed strictly.


Employers can make contributions to your FSA, but they are not required to. FSAs are limited to $2,650 per year per employee; if you’re married, your spouse can also put up to $2,650 in an FSA with their employer.15 FSA funds can be used to pay for not only your medical expenses but also medical expenses for your spouse and dependents. The funds cannot be used to pay for insurance premiums. The funds can be used for over-the-counter medicines with a doctor’s prescription (although insulin is allowed without a doctor’s prescription). They may also cover the cost of medical equipment.

Money put into your FSA by your employer that is not deducted from your wages is generally not counted against the FSA funding limit for the year. This means that if your employer contributes $1,000 to your FSA, you are generally still allowed to contribute the full $2,650 per year to your FSA. An exception to this would be if your employer’s FSA contribution comes from your employee benefits cafeteria plan, in which case your employer benefits would reduce the amount you can put into your FSA to a combined $2,650. In addition, if you have multiple employers offering FSAs, you may elect to defer an amount up to the limit under each employer’s plan; this differs from HSAs and IRAs, which only allow the combined funding up to a certain limit no matter how many accounts or employers you have.

Depending on the FSA, you may be allowed a grace period of up to two and a half extra months to use the money in the account or a carryover to the next year of up to $500. Only one of these options can be offered, and plans aren’t required to offer either one.

Carrying over a certain amount of money does not reduce the participant’s maximum FSA contribution for the next plan year. So, someone who carries over $500 from one plan year to the next can still contribute the maximum for the next plan year so they can get reimbursed for more than just the plan maximum for the next year.

Rules and Tax Implications

Generally, the money put into an FSA is not only exempt from your regular taxes but also not subject to payroll taxes for Medicare, Social Security, and Medicaid. This leads to an even higher tax savings than many other ways of saving money in a tax-benefited savings vehicle.

People who have high-deductible health plans with HSAs they are eligible to fund are generally not allowed to also have FSAs, except for a limited-expense FSA, which is also called a limited-purpose FSA account. This type of FSA can be used to reimburse dental and vision expenses as well as potentially eligible medical expenses incurred after the health plan deductible is met; however, it is important to understand the details of how this works for your particular plan before thinking about funding it with anything above the amount that can be rolled over or that you know you will need during the plan year. You may be able to extend your ability to keep your FSA money after you are laid off if you continue health coverage under the company’s COBRA health insurance or another arrangement.

In addition, there may be multiple types of FSAs offered through your employer, such as health and dependent care, but generally speaking, the money cannot be transferred from one type of account to another.

Dental Insurance

The cost of all types of health coverage has been on the rise, and dental insurance is no exception. In fact, dental care is not only more expensive, but employers are now putting more of the costs of dental insurance on their employees. This means it’s important to shop around before defaulting to your employer’s plan since you may find that an organization you belong to provides a plan that better fits your needs (e.g., professional organizations, AARP, and many other organizations offer group dental plans).

When comparing dental plans, it is important to not only look at cost but also make sure your dentist is considered in-network; if not, consider whether you are willing to switch to another dentist in the dental plan’s network. Dentists outside the plan may provide you with little to none of the plan benefits.

You may see dental plans list coverage with three numbers illustrating the percentage of particular services the plan will cover (100-80-50 plan). These numbers can be understood as follows:

  • 100: The plan covers 100% of preventative dental work, including regular check-ups and cleanings.
  • 80: The plan covers 80% of the cost for common dental procedures the plan covers. Common procedures include cavity fillings, braces, root canals, whitening, etc.
  • 50: The plan covers 50% of the cost for major dental procedures the plan covers. Major procedures include tooth crowning, tooth implants, procedures requiring sedation, etc.

Typically, plans will require you to pay a small deductible. They will cover a certain percentage of costs after the deductible has been met, depending on the category in which the procedure falls, up to a yearly cap, after which point you will have to pay all remaining costs.

Vision Insurance

Vision insurance commonly pays for the following:

  • Preventive care, including annual eye exams and check-ups;
  • Costs associated with contact lenses, lens frames, lenses, and lens protection methods;
  • Disposable contacts (typically an added coverage that costs more); and
  • Eye surgery discounts (typically an added coverage that costs more).

It’s important to note that it’s not uncommon for vision insurance providers to deny coverage for medical issues related to your vision. Should something come up during a check-up, your doctor will likely refer you to a specialist, the costs for which wouldn’t be covered by your vision insurance. The good news is that although vision insurance may not cover the cost of such medical issues, your health insurance would cover the costs more often than not.

Some important questions to ask yourself and your employer regarding your vision insurance include the following:

  • Does your vision insurance cover the costs of eye tests or exams you want or need?
  • Does your vision insurance cover the costs of glasses you want or need?
  • Does your vision insurance cover the costs of lenses you want or need?
  • Are you required to go to a low-cost chain store, or can you go to your private practice doctor?

Life Insurance/Accidental Death and Dismemberment

Life insurance offered through your employer is often a very good deal. Because the underwriting is done for the employer as a whole, it’s generally low cost; it may even be free. Signing up is easy since you are generally not required to undergo a physical exam to qualify, and it’s usually pretty inexpensive. The problem is that a person can often buy a limited amount of insurance through their employer’s plan, which may not be enough to cover the amount of life insurance you need.

How much life insurance is necessary?

Life insurance is looked at as an income replacement insurance plan in case someone passes away. To find the minimum amount of coverage you should have, figure out how much it would cost for your family to live without your income and replace that amount minus any growth on the assets you think they’ll receive. This involves thinking about things like additional childcare and someone to help around the house. It can help to figure out how much it costs for you to live currently and how much each partner earns, although the lifestyle costs may increase or decrease depending on the family dynamic.

As a very rough starting point, if you are the sole breadwinner, it is generally recommended to make sure your assets minus your house add up to at least roughly 20 times your yearly expenses (you should speak with your financial planner and insurance provider for a specific recommendation). If your assets do not add up to 20 times your yearly expenses, then the current amount of shortfall is a very easy way to gauge the least amount of life insurance you should purchase from your employer or other life insurance program if possible.

Change of Employment Status

Another important point to make about employer life insurance is that you may lose life insurance if you quit your job or get fired from your job. You may be unable to get private insurance, and your next employer may not offer insurance. Some employer-sponsored life insurance plans are portable, so you can take them with you if you leave the job, but it’s important to know what type of life insurance your employer offers so you can buy insurance on the open market if your employer does not provide enough or the right type of life insurance.

Short and Long-Term Disability Insurance

According to the Social Security Administration16 one in four people in their 20s working today will become disabled before retirement age. One way to hedge against a disability is via disability insurance, which gives you a portion of your pay if you can no longer work for a specific period. The cost of disability insurance through your employer is often very inexpensive, making it worth considering. A disability can be due to pregnancy, short-term illness, or long-term illness.

Strategies and Tax Implications

It is important to know how to structure the payments for your disability insurance. If you pay for disability insurance with FSA funds or other pre-tax dollars, you will have to pay taxes on the benefits if or when you use the disability insurance. If you pay for the disability insurance with after-tax dollars, the benefit will be tax free. Given that the disability insurance only covers a percentage of your pay, it’s generally advisable to use after-tax dollars to fund the benefits. Personal circumstances, such as an inability to fund with after-tax dollars or to gather funds to cover any shortfall between the cost of living and the after-tax value of your disability benefits in case of a disability, may change the calculation for which option is most beneficial to you.

If your employer pays for your coverage pre-tax, your benefits will be taxable.

28. Taxation of Employer Provided Disability Insurance

Critical Illness Insurance

Critical illness insurance pays out a lump sum if the employee gets cancer or another serious illness. The insurance may be part of a cafeteria plan in which you choose how much money goes to which benefits, you may have to pay for the insurance out of withholding from your paycheck, or your employer may pay for the coverage. Remember that the benefits generally will not be taxed if the employee pays the full premium with after-tax money, whereas the lump sum payments will be taxed if the employer pays the cost with pre-tax money.

Coverage and Cost

The policy can be small or can cover as much as a million dollars per issue. So, it’s important to know how much coverage you need in coordination with any long-term care and disability insurance should you contract a major illness. Different policies cover different things, including:

  • Heart attack
  • Cancer
  • Heart transplants
  • Coronary bypass surgery
  • Parkinson’s disease
  • Alzheimer’s
  • Amyotrophic lateral sclerosis
  • Loss of sight
  • Loss of speech
  • Loss of vision
  • Heart valve replacement
  • Angioplasty
  • Kidney failure
  • Major organ transplant
  • Stroke
  • Paralysis

Keep in mind that each of these illnesses must meet the specific definition of the illness from the insurer; some cancers, strokes, etc. that you think will qualify don’t in fact qualify for a payout or only qualify for a partial payment. Likewise, some policies may require you to see a specialist in the particular field of your illness to qualify as having the disease properly diagnosed. So, it is important to know what your insurance actually covers.

It is often wise to consider disability, long-term care, and life insurance as the first places for insurance coverage money to be placed before looking at critical illness insurance. Keep in mind that self-insuring runs the risk that you contract a critical illness early on in life (in which case the insurance would have paid a significant return). If you do need coverage, this type of insurance can be very beneficial since the lump sum can be used to pay for things that aren’t covered by insurance, such as:

  • Some of your pay while not working
  • Travel costs to specialists
  • Specialists not covered by insurance
  • Experimental treatments not covered
  • Replacement of spouse’s income while they care for you
  • Health insurance premiums while you’re not working
  • Time off work
  • Out-of-network doctors & hospitals
  • Rent & Utilities
  • Mortgage & real estate taxes
  • Credit card bills
  • School tuition
  • Food

Insurers may provide up to a certain amount through your employer without going through a medical exam; however, amounts over that limit will require a physical. It’s important to make sure a failed health exam will not preclude you from getting the employer’s group coverage with no underwriting. To ensure that you’re protected in this scenario, you want to max out the available employer group coverage without underwriting while going through the underwriting just in case you fail the health exam and can’t get anything above the group coverage if that strategy is possible. Whether you go through your employer or an open-market plan from an insurance broker, you don’t want them to find cancer during underwriting, thus disqualifying you for any coverage, when you could have taken advantage of the group coverage prior to having the physical and finding out about the medical ailment. The group coverage will often require you to answer a few questions before providing the coverage you want.

Generally speaking, it is better to prioritize life insurance and disability coverage and then look to critical illness insurance since it is narrower in scope and it can be expensive. Of course, this changes for very cheap or free coverage or if your family has a medical history of critical illnesses. It is important to consider this in the hierarchy of insurance needs and decide where to spend your dollars to get the most benefit in terms of coverage and the way things will affect your life. I recommend speaking to a financial planner and insurance agent before making any decisions. The coverage may include only you or cover your spouse or domestic partner, your children, or family, so is important to know who can be covered and make sure you have thought about an objective for the appropriate coverage.

What the insurance covers can be very specific, so it’s important to know all the terms of the contract. Are pre-existing conditions covered? Which types of cancers and heart attacks are covered? Are some treatment payouts only partially covered, such as certain treatments for heart issues or cancers? Can you get a one-time payout or can you receive payments multiple times for the same illness or different illnesses over time? Do the policies require that you be hospitalized or receive chemotherapy or radiation to qualify? Is there an age-related benefit deduction (i.e., as you grow older, will the benefits decrease)? Is the policy portable (i.e., what happens if you switch jobs, retire, get laid off, or get fired)?

Payout Policy

Some policies provide multiple cash payments, such as for someone who has a heart attack followed by a kidney transplant, so the insurance will make multiple payouts from the same policy. On the other hand, some policies will only give a single payout for the first of the two issues. In addition, some policies will grant a second payout for a second occurrence of the same event, such as the second occurrence of a heart attack, although the second payout may be lower.

You may find that different illnesses provide different payouts as a percentage of the full value of the coverage (i.e., some cancers may pay out 100% while other cancers pay out 25%; skin cancer pays out a flat rate far lower that is not tied to the total coverage amount). There may also be a requirement that a certain amount of bodily damage be done in addition to the disease diagnosis to qualify for a payment.

The coverage may also provide an additional stipend for certain treatments, transportation, or lodging in association with the covered illness. Likewise, lifestyle choices, such as drug use, flying small planes, alcohol abuse, being part of a war or riot, or self-inflicted injuries, or how the illness was acquired may change your coverage. Some insurers require you to live for a certain period after a diagnosis, so someone who has a heart attack but dies the next week may not be covered for a payout under the policy.


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Feel free to contact Josh Mungavin with any questions by phone 1.800.448.5435 extension 219, or email: [email protected].

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