What is a health savings account (HSA) and how do I know if I should have one?

A Health Savings Account (HSA) is a tax-advantaged personal savings account meant for medical expenses. Often called a "triple-tax-advantaged" account, it is widely considered one of the best wealth-building and tax-saving tools available—provided you meet the right criteria.

The "Triple Tax Advantage" of an HSA

Unlike a Flexible Spending Account (FSA), HSA money never expires . It rolls over year after year, stays with you even if you change jobs or leave your employer, and once you turn 65, you can withdraw money for any purpose penalty-free (though non-medical withdrawals are taxed as ordinary income).

The Catch: You Need a High-Deductible Health Plan (HDHP)

You cannot just open and contribute to an HSA anytime. To be eligible, you must be enrolled in an IRS-qualified High-Deductible Health Plan (HDHP).

For 2026 , the IRS defines an HDHP as having:

• Minimum Deductible: $1,700 for self-only coverage ($3,400 for family coverage).
• Maximum Out-of-Pocket Limit: $8,500 for self-only coverage ($17,000 for family coverage).

The maximum you can contribute to an HSA is capped annually. For 2026 , the contribution limits are $4,400 for self-only coverage and $8,750 for family coverage (with an extra $1,000 catch-up contribution allowed if you are 55 or older).

How to Know If You Should Have an HSA

An HSA is a fantastic fit for some people, but a poor choice for others. Consider the following questions to decide:

You SHOULD consider an HSA if:

• You are relatively healthy and rarely see the doctor: If your typical medical care consists of an annual physical and a routine prescription, an HDHP lets you lower your monthly insurance premiums while saving money tax-free for future health needs.
• You want an extra retirement vehicle: Once your HSA balance crosses a certain threshold (usually set by the provider), you can invest the funds in mutual funds or ETFs (similar to a 401(k) or IRA). If you can afford to pay your current medical bills out of pocket and let the HSA invest and grow untouched, it becomes a powerful tax-free retirement fund for healthcare costs in old age.
• You have steady cash flow to cover the deductible: You should feel confident that if a sudden medical emergency or accident happens, you can comfortably afford to pay out-of-pocket up to your deductible limit before insurance kicks in.

You SHOULD NOT (or may want to rethink) an HSA if:

• You have chronic medical conditions or high predictable medical costs: If you regularly hit your maximum out-of-pocket or have heavy prescription drug/specialist costs every month, a traditional, low-deductible health plan often saves you more money overall, even with higher monthly premiums.
• You live paycheck-to-paycheck: If a sudden $1,500 medical bill would throw your finances into crisis, a high-deductible plan can be risky. You need cash availability to handle the initial cost burden of an HDHP.
• You don't have the discipline to save/invest: If having a lower premium means you just spend the difference rather than saving it into the HSA, you won't have the funds available when a medical need actually arises.

You can check official IRS guidelines and rules on health plans via the IRS Health Savings Accounts Page.

To help narrow down whether an HDHP + HSA makes financial sense for you, tell me:

• Do you have predictable ongoing medical expenses (like regular prescriptions or therapies)?
• Would you be comfortable paying out-of-pocket for a sudden medical emergency?

What is an HSA?

A Health Savings Account (HSA) is a tax-advantaged account you can use to pay for qualified medical expenses—things like deductibles, copays, prescriptions, dental care, and vision expenses.

The big attraction is the triple tax advantage:

1. Contributions can be tax-deductible. If your employer lets you contribute through payroll, they can generally also avoid federal income and payroll taxes.
2. Money grows tax-free. You can generally earn interest or investment returns without owing federal tax on the growth.
3. Withdrawals for qualified medical expenses are tax-free.

And unlike an FSA, the money is yours. It generally rolls over from year to year and stays with you if you change jobs.

Who can have one?

The key question is whether your health insurance makes you HSA-eligible.

For 2026, a standard qualifying high-deductible health plan (HDHP) generally needs a deductible of at least:

• $1,700 for individual coverage
• $3,400 for family coverage

and its out-of-pocket maximum generally can't exceed $8,500 individual / $17,000 family.

There are also restrictions involving other health coverage, Medicare, being someone else's tax dependent, and certain FSAs/HRAs.

One 2026 change worth knowing: certain bronze and catastrophic plans are now treated as HSA-compatible, expanding eligibility.

How much can you put in?

For 2026, the total contribution limit—including employer contributions—is:

• $4,400 for self-only coverage
• $8,750 for family coverage

So if your employer puts $1,000 into your HSA, for example, that counts toward your $4,400/$8,750 limit.

Should you have one?

An HSA is particularly attractive if:

• Your employer offers an HSA-eligible health plan.
• Your employer contributes money to the HSA. That's essentially part of your compensation, so it's worth taking advantage of.
• You're reasonably healthy and don't expect large medical expenses.
• You can afford to cover a relatively high deductible if something unexpected happens.
• You want another tax-advantaged way to save for retirement.
• You can afford to leave some HSA money invested rather than spending it immediately.

An HSA may be less attractive if:

• You expect substantial medical expenses and a lower-deductible insurance plan would save you more overall.
• You don't have enough emergency savings to comfortably handle the HDHP's deductible.
• The HSA plan has significantly higher out-of-pocket costs or premiums than your alternative plan.
• You aren't actually eligible to contribute.

The important part: don't compare the HSA by itself

If you're choosing between two insurance plans, don't simply ask, "Is an HSA good?"

Compare the entire package:

Annual premiums + expected medical costs + employer HSA contribution + tax savings + worst-case out-of-pocket costs.

For example, an HSA plan might have a $500/month premium and a $4,000 deductible, while a traditional plan costs $650/month with a $1,500 deductible. The HSA plan could be substantially cheaper overall—but it could also be worse for someone who expects a lot of medical care.

A simple rule of thumb

If you have an HSA-eligible plan and your employer contributes to the HSA, I'd generally lean toward using the HSA, provided you can comfortably handle the deductible.

If you're deciding between health insurance plans, though, we should actually run the numbers. That's where the answer can change.

If you tell me your monthly premiums, deductible, out-of-pocket maximum, copays/coinsurance, employer HSA contribution, and whether it's individual or family coverage, I can compare the plans and show you which one is likely better.

A Health Savings Account (HSA) is a tax-advantaged personal savings account meant to be used for medical expenses. Often called a "triple-tax-advantaged" account, it is widely considered one of the best wealth-building and financial planning tools available—if you qualify.

What Makes an HSA Unique (The Triple Tax Advantage)

1. Contributions are tax-deductible (or made pre-tax if done via payroll deduction), lowering your taxable income for the year.
2. Growth is tax-free if you invest the funds in mutual funds, stocks, or bonds inside the account.
3. Withdrawals are tax-free when used for qualified medical expenses (like doctor visits, prescriptions, dental care, and vision).

Unlike a Flexible Spending Account (FSA), HSA money never expires . It rolls over year after year, stays with you even if you change jobs or leave your employer, and after age 65, you can withdraw money for any purpose penalty-free (though non-medical withdrawals are taxed as ordinary income).

Basic Eligibility: How Do You Qualify?

You cannot just open and contribute to an HSA anytime. To be eligible, you must meet strict IRS criteria:

• You must be covered by a High-Deductible Health Plan (HDHP).
• For 2026, an HDHP is defined as a plan with a minimum annual deductible of $1,700 for self-only coverage or $3,400 for family coverage.
• You cannot be covered by any other non-HDHP health insurance (such as a spouse's traditional plan, Medicare, or standard Medicaid).
• You cannot be claimed as a dependent on someone else's tax return.

Should You Have an HSA? (Pros & Cons)

An HSA is a great fit if:

• You are relatively healthy and don't visit the doctor often: You pay lower monthly insurance premiums with an HDHP, and you can sock away cash tax-free for future health needs.
• You want an extra retirement vehicle: Once you max out standard retirement accounts (like a 401(k) or IRA), an HSA functions like a "super IRA" for healthcare costs in your older years.
• You can afford to pay medical out-of-pocket costs and leave the HSA invested: The real magic happens if you pay for today's minor doctor visits out of your regular cash flow and let your HSA balance compound and grow untouched for decades.

An HSA might not be right if:

• You have chronic medical conditions or high predictable healthcare costs: If you know you will hit your maximum out-of-pocket limit every year, a traditional, lower-deductible health plan with higher premiums might actually save you more total money than an HDHP.
• You live paycheck-to-paycheck: If a sudden medical emergency would wipe you out before you could build up a balance in the account, the high deductible of an HDHP could create a financial strain.

If you'd like, share:

• Your approximate healthcare needs for the year (e.g., routine checkups vs. ongoing prescriptions/procedures)
• Whether your employer offers an HSA match or contribution

I can help you crunch the numbers to see if an HDHP/HSA combo makes financial sense for you.

An HSA (Health Savings Account) is a tax-advantaged account you can use to pay for qualified medical expenses. Think of it as a health-care savings account that can also function a bit like a retirement account.

Why HSAs are attractive

HSAs have unusually strong tax benefits:

• Contributions can be tax-deductible (or pre-tax if made through payroll).
• Investment growth is tax-free.
• Withdrawals for qualified medical expenses are tax-free.
• Money generally rolls over indefinitely—you don't have to spend it by the end of the year.
• The account belongs to you, so it generally stays with you if you change jobs.

That's why some people intentionally leave their HSA money invested and pay medical expenses out of pocket when they can afford to. Later, they can reimburse themselves for eligible expenses, even years later, provided they kept the appropriate records.

Who can have one?

The big catch is that you generally need an HSA-eligible health insurance plan, usually a high-deductible health plan (HDHP). You also generally can't be enrolled in Medicare or have other disqualifying health coverage.

For 2026, the IRS says the HSA contribution limit is:

Employer contributions count toward those limits.

There is also an important 2026 change: all Bronze and Catastrophic plans offered through the ACA Marketplace are HSA-compatible, subject to the applicable rules.

Should you have one?

I'd generally lean yes if all or most of these describe you:

• Your employer offers an HSA-eligible health plan.
• The plan has a meaningfully lower premium than its traditional alternative.
• Your employer contributes money to the HSA. That's essentially free compensation, so it's particularly valuable.
• You can comfortably handle the plan's deductible if something unexpected happens.
• You don't expect extremely high medical expenses every year.
• You want another tax-advantaged way to save for retirement.
• You can afford to leave some HSA money invested rather than immediately spending it.

I'd be more cautious if:

• You have substantial, predictable medical expenses every year.
• The HDHP's deductible/out-of-pocket maximum would be difficult for you to cover.
• The premium savings are small compared with the additional financial risk.
• You'd have to go into debt to cover a large medical bill.

The key isn't actually "HSA vs. no HSA"

The more important question is usually:

"Which health insurance plan is the better deal for me: the HSA-eligible plan or the traditional plan?"

An HSA can make a high-deductible plan substantially more attractive, but you shouldn't choose an HDHP just because HSAs have great tax advantages.

A good comparison is:

Annual premiums − employer HSA contribution + expected medical costs + potential tax savings

Then compare that with the traditional plan, while also considering the worst-case out-of-pocket cost.

If you give me the details of the health plans available through your employer (premium per paycheck, deductible, out-of-pocket maximum, copays/coinsurance, and employer HSA contribution), I can compare them and tell you which one is likely to be better financially.

A Health Savings Account (HSA) is a tax-advantaged account you can use to pay for eligible healthcare expenses. Think of it as a personal healthcare savings/investment account that you own—not something you lose if you change jobs.

How an HSA works

You generally need to be enrolled in an HSA-eligible high-deductible health plan (HDHP) to contribute. You put money into the HSA, typically through payroll, and use it for qualified expenses such as deductibles, copays, coinsurance, prescriptions, and certain dental/vision expenses.

The big attraction is the triple tax advantage:

1. Contributions can be tax-free/deductible (and payroll contributions can avoid certain payroll taxes).
2. Investment growth is tax-free.
3. Withdrawals are tax-free when used for qualified medical expenses.

Unused money rolls over indefinitely rather than expiring.

For 2026, the contribution limits are $4,400 for individual coverage and $8,750 for family coverage. The employer can contribute toward those limits too.

Should you have one?

An HSA is often attractive if:

👍 An HSA may be a good choice if:

• You're relatively healthy and don't expect frequent medical expenses.
• Your employer offers an HSA-compatible plan with a meaningfully lower premium.
• You have enough savings to handle the plan's potentially high deductible.
• Your employer contributes money to your HSA.
• You want another tax-advantaged way to save for retirement/healthcare.

🤔 Think twice if:

• You regularly have expensive medical care, medications, or specialist visits.
• The HDHP's deductible and out-of-pocket maximum are difficult for you to afford.
• A traditional plan has substantially better coverage for only a modestly higher premium.
• You don't have enough cash reserves to cover a large medical bill.

The key is not to compare the plans based only on their monthly premiums. Compare:

Annual premiums + expected healthcare costs − employer HSA contribution

Also look at the out-of-pocket maximum. That's particularly important because an HSA-compatible plan can have a lower premium but expose you to more costs when you actually need care.

A simple example

Suppose you have two choices:

The HSA plan effectively starts $2,200 ahead ($1,200 lower premiums + $1,000 employer contribution), but you'd need to be comfortable with the higher deductible if something goes wrong.

That's why an HSA isn't automatically better—it depends heavily on the specific insurance plans and your expected healthcare usage.

One interesting 2026 change: more plans are now HSA-compatible. In particular, all 2026 Marketplace Bronze and Catastrophic plans are HSA-compatible, while other plans can qualify depending on their design.

If you tell me (1) your monthly premium, (2) deductible, (3) out-of-pocket maximum, (4) copays/coinsurance, and (5) how much your employer puts into the HSA, I can compare your HSA plan against your other insurance option and tell you which is likely better financially.

A Health Savings Account (HSA) is a tax-advantaged personal savings account that you can use to pay for qualified medical expenses. It is designed specifically for people who are enrolled in a High-Deductible Health Plan (HDHP).

Key Features of an HSA

• Triple tax advantage: Contributions are 100% tax-deductible (or made pre-tax via payroll deduction), money grows tax-free through investments, and withdrawals are entirely tax-free if used for qualified medical expenses.
• Rolls over year-to-year: Unlike a Flexible Spending Account (FSA), the money in an HSA never expires or disappears at the end of the year. It stays with you even if you change jobs, switch health plans, or retire.
• Investment potential: Once your balance reaches a certain threshold, you can invest the funds in stocks, bonds, or mutual funds to grow your wealth over time.
• Ownership: The account belongs completely to you, not your employer.

How to Know If You Should Have an HSA

An HSA is an incredible financial tool, but it requires the right health and financial situation to make sense.

• You should consider an HSA if:
  • You have a high-deductible health plan: By definition, you must be enrolled in an IRS-qualified HDHP to contribute to an HSA.
  • You are relatively healthy and don't visit the doctor often: If you only need routine preventative care (which is 100% covered by insurance even under an HDHP) and rarely have high medical costs, you benefit from lower monthly premiums and can stockpile tax-free savings.
  • You want a supplemental retirement vehicle: If you max out your other retirement accounts, an HSA acts like a "super IRA." After age 65, you can withdraw money from an HSA for any purpose penalty-free (though you pay ordinary income tax if it's not for medical expenses).
  • You can afford to pay out-of-pocket for medical care upfront: To maximize the tax benefits, you should ideally pay for minor doctor visits out of pocket and let your HSA balance grow and compound over time.
• You might want to skip an HSA (or choose a traditional plan) if:
  • You have chronic medical conditions or high predictable healthcare costs: If you know you will hit your deductible every year due to regular prescriptions, therapy, or scheduled surgeries, a traditional lower-deductible plan with higher premiums might actually save you more money overall.
  • You live paycheck-to-paycheck: If a sudden medical emergency would wipe you out before you could build up a cushion in your HSA, the high deductible of an HDHP could create financial stress.

If you'd like, let me know:

• Your approximate annual medical expenses or prescription needs
• Your comfort level with financial risk and high deductibles

I can help you run a quick comparison between an HDHP/HSA combo and a traditional health plan.

A Health Savings Account (HSA) is a special savings/investment account you can use for qualified medical expenses. The big attraction is the tax advantage:

• Money you contribute can reduce your taxable income.
• You can withdraw it tax-free for qualified medical expenses.
• The money rolls over indefinitely—you don't lose it at the end of the year.
• The account stays yours if you change jobs.
• You can potentially invest the balance and let it grow tax-free.

The catch: you need an HSA-eligible health plan

You generally have to be enrolled in a qualifying high-deductible health plan (HDHP) to contribute to an HSA. For 2026, the IRS defines an HSA-qualified HDHP as having at least a $1,700 deductible for individual coverage or $3,400 for family coverage, with maximum out-of-pocket costs of $8,500/$17,000 respectively.

For 2026, you can contribute up to:

Those limits include contributions from both you and your employer.

So, should you have one?

An HSA is especially attractive if:

You probably should consider one if:

• Your employer offers an HSA-compatible health plan.
• The HSA plan has significantly lower premiums than your other options.
• You don't have extremely high medical expenses every year.
• Your employer contributes money to the HSA—this is essentially part of your compensation.
• You can afford to cover a relatively high deductible if something unexpected happens.
• You like the idea of saving for future medical expenses while getting tax benefits.

You might prefer a traditional health plan if:

• You have frequent or expensive medical care and the HDHP's deductible/out-of-pocket costs would be burdensome.
• You have expensive prescriptions or ongoing treatments.
• You don't have enough savings to comfortably handle the HDHP's deductible.
• The HSA plan's premium savings aren't large enough to compensate for its higher cost-sharing.

One important way to think about it

Don't compare plans based only on the monthly premium.

For example:

Traditional plan

• Premium: $300/month
• Deductible: $1,500
• Out-of-pocket max: $5,000

HSA plan

• Premium: $200/month
• Deductible: $3,500
• Out-of-pocket max: $6,500
• Employer HSA contribution: $1,000/year

The HSA plan saves you $1,200/year in premiums + $1,000 from your employer, before even considering the tax benefit. That could make the higher deductible worthwhile.

On the other hand, if you know you're going to spend $5,000+ on healthcare every year, the traditional plan could easily come out ahead.

There's also a retirement benefit

This is one of the most overlooked parts of HSAs. You don't have to spend the money immediately. You can pay medical bills out of pocket, keep receipts, and allow the HSA to grow. Later, you can reimburse yourself for those qualified expenses. After age 65, you can also withdraw HSA money for non-medical purposes, although those withdrawals are generally taxable; qualified medical withdrawals remain tax-free.

So an HSA can function somewhat like a medical-specific retirement account.

One caveat: eligibility can be affected by other coverage, Medicare enrollment, being claimed as someone else's dependent, and certain FSAs/HRAs.

If you tell me your health insurance options (monthly premium, deductible, out-of-pocket max, copays/coinsurance, and any employer HSA contribution), I can compare the plans mathematically and tell you which one is likely to be better for you.

A Health Savings Account (HSA) is a tax-advantaged personal savings account that you can use to pay for qualified medical expenses. It is designed specifically for people who are enrolled in a High-Deductible Health Plan (HDHP).

Key Features of an HSA

• Triple Tax Advantage: Contributions are 100% tax-deductible (or made pre-tax via payroll deduction), funds grow tax-free through interest or investments, and withdrawals are completely tax-free when used for qualified medical expenses.
• Ownership: The account belongs entirely to you. Unlike a Flexible Spending Account (FSA), the money in an HSA never expires or "rolls over"—it rolls over indefinitely year after year.
• Portability: If you change jobs, switch health insurance plans, or retire, the HSA and all of its funds go with you.
• Investment Potential: Once your balance reaches a certain threshold set by your financial custodian, you can invest the money in mutual funds, stocks, or bonds much like a 401(k) or IRA.

Eligibility Requirements

To open and contribute to an HSA, you must meet the following criteria:

• You must be enrolled in an IRS-defined HDHP.
• You cannot be covered by any other non-HDHP health insurance (such as a spouse's traditional plan, standard Medicare, or secondary insurance).
• You cannot be claimed as a dependent on someone else's tax return.

How to Know If You Should Have One

An HSA is a powerful financial tool, but it is not the right fit for everyone. Consider the following factors to see if it aligns with your situation:

• Your Medical Needs:
  • Good fit: You are generally healthy, rarely go to the doctor except for annual preventive care (which is 100% covered under HDHPs by law), and want a safety net for unexpected future healthcare costs.
  • Poor fit: You have chronic medical conditions, take expensive regular prescriptions, or anticipate major medical procedures (like surgery or having a baby) in the near future. In these cases, the high deductible of an HDHP might cost you more out-of-pocket than a traditional low-deductible plan.
• Your Cash Flow / Budget:
  • Good fit: You have enough room in your monthly budget to comfortably pay for routine care out-of-pocket until you meet your deductible, allowing you to leave the HSA funds untouched to grow.
  • Poor fit: You live paycheck-to-paycheck and would struggle to pay for a doctor's visit or prescription before meeting your deductible.
• Your Retirement Savings Goals:
  • Good fit: You have already maxed out other retirement accounts or want an extra tax-sheltered vehicle. After age 65, you can withdraw money from an HSA for any purpose penalty-free (though non-medical withdrawals are taxed as ordinary income, mirroring a traditional IRA).

If you'd like, tell me:

• What are your approximate annual medical expenses?
• Are you choosing between an HDHP and a traditional PPO/HMO right now?

I can help you crunch the numbers to see which plan makes the most financial sense.

A Health Savings Account (HSA) is a tax-advantaged personal savings account that you can use to pay for qualified medical expenses. To be eligible to contribute to an HSA, you must be enrolled in a specific type of health insurance known as a High-Deductible Health Plan (HDHP).

Key Benefits of an HSA (The "Triple Tax Advantage")

• Tax-deductible contributions: Any money you put into the account reduces your taxable income for that year.
• Tax-free growth: Any interest or investment earnings inside the account grow completely tax-free.
• Tax-free withdrawals: Withdrawals are 100% tax-free when used for qualified medical expenses (such as doctor visits, prescriptions, dental care, and vision needs).

How to Know If You Should Have One

An HSA and an HDHP setup works wonderfully for some people, but it can cost more than a traditional plan for others. Consider the following factors to see if it fits your lifestyle and financial goals:

• Your Medical Needs:
  • Good fit: You are generally healthy, rarely see a doctor outside of an annual physical, and don't take regular expensive prescriptions.
  • Bad fit: You have chronic medical conditions, see specialists regularly, or anticipate major surgery or a scheduled medical event (like having a baby) in the near future.
• Cash Flow and Savings:
  • Good fit: You have enough cash flow or emergency savings to comfortably pay for out-of-pocket medical costs up to your deductible before your insurance kicks in.
  • Bad fit: A sudden medical bill of $1,000 to $2,000 would throw your personal finances into a crisis.
• Investment and Wealth Building:
  • Good fit: You already max out or want an additional vehicle to save for retirement. Once your balance crosses a certain threshold, many HSA providers let you invest the funds in mutual funds or stocks, making it act almost like a super-charged IRA for health care costs in retirement.

If you'd like, tell me:

• Your approximate medical usage in a typical year
• Whether you are deciding between an HDHP and a traditional PPO/HMO option through your employer

I can help you crunch the numbers to see which plan might save you more money.

A Health Savings Account (HSA) is a special savings/investment account you can use for healthcare expenses if you're enrolled in an HSA-eligible high-deductible health plan (HDHP).

The big attraction is the triple tax advantage:

1. Money going in can be tax-free — contributions can reduce your taxable income.
2. Money in the HSA can grow tax-free — including interest/investment gains.
3. Money coming out is tax-free when used for qualified medical expenses.

And unlike an FSA, the HSA generally stays yours if you change jobs and unused money rolls over year after year.

Who can have one?

For 2026, you generally need an HSA-eligible HDHP and cannot have disqualifying additional coverage. You also generally can't be enrolled in Medicare or claimed as someone else's dependent.

For 2026, the HSA contribution limits are:

Those limits include contributions from you and your employer combined.

So, should you have one?

An HSA is particularly attractive if:

👍 An HSA may be a good choice if:

• Your employer offers an HSA-eligible health plan.
• Your employer contributes money to the HSA. That's essentially free compensation.
• You don't expect very high medical expenses.
• You can afford to cover a relatively large deductible if something unexpected happens.
• You want another tax-advantaged way to save for retirement.
• You can leave money in the HSA rather than spending every dollar immediately.

🤔 Think twice if:

• You have frequent medical expenses or expensive prescriptions.
• You couldn't comfortably handle the plan's deductible/out-of-pocket maximum.
• The HDHP has significantly higher costs or worse coverage than your alternative plan.
• Your employer offers a generous traditional plan that's cheaper for your particular healthcare usage.

One important distinction: don't choose an HDHP solely because "HSA = good." Compare the entire health plan, including premiums, employer HSA contribution, deductible, copays/coinsurance, and out-of-pocket maximum.

A simple example

Suppose you have two options:

• Plan A: $150/month premium, $1,500 deductible
• Plan B: $80/month premium, $3,500 deductible + HSA
• Employer puts $1,000/year into the HSA

Plan B saves you $840/year in premiums plus gives you $1,000 from your employer, but you'd have more exposure to medical costs before insurance kicks in.

If you're relatively healthy and can handle the deductible, Plan B + HSA could be excellent. If you know you'll have $5,000+ of medical expenses every year, Plan A might come out ahead.

One of the best ways to decide is to compare your actual employer plans mathematically. If you give me the numbers for your health-insurance options—monthly premiums, deductibles, out-of-pocket maximums, copays/coinsurance, and any employer HSA contribution—I can calculate which one is likely better for you in low-, medium-, and high-medical-expense scenarios.