Health Insurance With Multiple Jobs

Health Insurance With Multiple Jobs

For the multi-jobbers, coordinating health insurance with multiple jobs is a high-wired act. Here’s some good news: you can have multiple health insurance plans from different employers! While we won’t dissecting the whole health insurance market, you should walk away from this article knowing:

1) Yes, you can be overinsured. No one, especially your employers, will care. Your health care plan is entirely your own business. To further complicate matters, there’s also the once-a-year enrollment period, with off-cycle “qualifying events” allowed only when you (gulp) qualify.

2) The health insurance market allows for coordination of benefits between primary and secondary plans. If you’re paying, then you should ask your providers to perform coordination of benefits and multi-claim.

Now let’s break down some common approaches the Overemployed can take with health insurance with multiple jobs.

Simplest Solution: Stick With Your Primary Job’s Health Insurance Plan

If J1 is your long-term cash cow, then the simplest solution is to stick with your current health insurance plan. Do this even if J2’s health insurance plan is better or cheaper. When in doubt, always KISS (keep it simple stupid). You’re already executing a complex game plan by working two remote jobs at once. Why create an additional stressor for yourself?

Overlapping Health Insurance With Multiple Jobs: The Curious Case Of The Double Insured

For a majority of you, the most likely case is running into overlapping health insurance plans. This is especially true if you enroll in J2’s health insurance when you joined. For a period of 12 months or less (depending on enrollment periods), you’ll be double insured until you can disenroll from J1’s health plan. While paying two insurance premiums isn’t ideal, it’s still far better than not being insured at all. Plus, there’s a tax penalty for not having health insurance. So why not just KISS and have double coverage for a little bit.

Here’s the bonus. Remember the “coordination of benefits” concept discussed earlier? Now with double insurance, you can get some elective healthcare taken care of like skincare or braces at less cost. Caveat: do check with your insurance plans and providers on costs before proceeding.

Also, overlapping health insurance isn’t as uncommon as you’d think. This happens often for those with government health benefits like medicare or medical benefits for military veterans. Now this curious case is happening with the Overemployed as well.

Health Savings Accounts and High Deductible Health Plan For Multi-Jobbers

Remember in the intro we mentioned tax incentives? When in doubt, IRS publication 969 is the source document for what we’re saying here. We recommend you “google” and download the latest PDF for a quick read. We’re not linking it here because the information changes with each tax year.

Health savings accounts, or HSA, let people set aside money pre-tax for health and medical expenses not covered by their insurance plan. There’s never a deadline for using money in an HSA, and the account goes with you if you change jobs. Your HSA accounts must be paired with an HSA-compatible high deductible health plan. For 2022, contributions may be as high as $3,650 for individuals and $7,300 for family coverage. People 55 and older can set aside an additional $1,000 in catch-up contributions. Some employers will offer an HSA employer contribution as well.

#1 Thou shalt have one, and only one, high deductible health plan with a health savings account

Much like multiple 401Ks, the Overemployed can have multiple health insurance plans. However, there’s an exception when enrolling in a high deductible health plan (HDHP). An HDHP is a health plan that qualifies you for an employer-contributed health savings account or HSA. Now the HSA is what financial planners call a triple tax-advantaged investment vehicle (even better than the double tax-advantaged Roth). There’s only one catch – HSA can only be used for medical expenses tax-free, for all other use you’ll have to pay taxes and a 20% penalty (ouch). Once you reached 65, the magical “triple bottom line” happens: you contribute tax-free, use the contribution tax-free for medical expenses, and withdraw tax-free. More on HSA investing and how withdrawal works in another post.

Bottom line: HSA is a tax-exempt account to help defray high out-of-pocket costs when you’ve covered under a HDHP.

An HDHP, as the name suggests, is a high deductible health plan. That means you’ll have to pay more out-of-pocket before the HDHP will kick in to cover the costs. As a result, the IRS allows a tax-advantaged HSA ($7,100 contribution limit in 2020) for employers to contribute and subsidize the high out-of-pocket costs. However, this isn’t charity. Employers offer HDHPs to save on healthcare costs. Young employees in good health should enroll in HDHP to pocket the employer’s HSA contributions, assuming no major health needs. It’s a healthcare casino royale!

Per IRS Pub 969: if you enrolled in a high-deductible health plan, then you CANNOT have any other medical health insurance. Read carefully here. You basically cannot have a “coordination of benefits” with dual insurance if you participate in HDHP with HSA.

#2 Thou can have multiple dental and vision plans still while in a high deductible health (medical) plan

The IRS, however, does allow you to shop around for better or lower-cost dental and other health insurance coverages. See below directly from IRS Pub 969 on “Other health coverage.”

Other health coverage.

If you (and your spouse, if you have family coverage) have HDHP coverage, you can’t generally have any other health coverage. However, you can still be an eligible individual even if your spouse has non-HDHP coverage, provided you aren’t covered by that plan.

You can have additional insurance that provides benefits only for the following items.

  • Liabilities incurred under workers’ compensation laws, tort liabilities, or liabilities related to ownership or use of property.
  • A specific disease or illness.
  • A fixed amount per day (or other period) of hospitalization.

You can also have coverage (whether provided through insurance or otherwise) for the following items.

  • Accidents.
  • Disability.
  • Dental care.
  • Vision care.
  • Long-term care.
  • Telehealth and other remote care (for plan years beginning before 2022).

Key Takeaways

When it comes to healthcare, the Overemployed Way is to keep it simple. You should focus your energy on 2x-ing your income instead. Here’s a quick recap:

  1. Stick with one primary employer for medical insurance
  2. Double health insurance is better than gapping coverage when switching cash cows
  3. Only play in the healthcare casino royale (HDHP with HSA) if you’re healthy or can stomach the risks
  4. When in doubt, elect the option that gives you better sleep at night

Here’s what we don’t want: you or a family member fall ill and find out healthcare costs are uncapped. That defeats the point of being Overemployed and having early financial freedom. Practice KISS instead. Cue the Geico commercial…


  1. Hello,

    Which insurance w0uld be primary if I have coverage from each of my employers? Let’s say I work an equal amount of hours in each job if that’s a determining factor. What would determine my coordination of benefits? Would it be the insurance I’m covered with first would be my primary?

  2. I work 2 remote jobs (J1 and J2) Each of the employer are large organizations(more than 50 employees). I had health insurance from J1 for me and my family. When I took up job J2 I cancelled my health insurance from J1 and enrolled in my wife’s employers insurance(my wife works for a different employer and her employer has good health insurance plans).
    I have received 1095 C from both of my employers at J1 and J2. The payroll for J2 is managed by ADP and in the ADP portal(when I login to my account on the ADP portal) it is showing me the 1095C from J1 also (in addition to the 1095C of J2).
    So my question is will my employers (at J1 or J2) have access to my 109C forms from the other employer or will they know that I’m employed at the other job.

  3. Hi Isaac,

    Great information. I’m hoping you can help me as well. I’m considering changing from my PPO’s to HDHP’s. I feel like there’s too much to consider. Here’s some of my stats.

    $0 for all plans including HDHP for family coverage
    $1400 HDHP deductible
    $3000 employer contribution to HSA

    $135/mo for HDHP family coverage
    $1400 HDHP deductible
    $1800 employer contribution to HSA

    My question is can I contribute to both and HSA’s up to the annual max to take advantage of the “free” money with hopes we won’t use it and can invest?
    Will I have to pay both deductibles sucking up all the “free” money? Would it make sense? Anything else I should consider with this option?


    Should I just keep J1 PPO family coverage for $0 and supplement with J2: HDHP for $135 without a HSA and instead get a FSA with a partial company match for additional medical expenses even though I can’t invest it?

    Thanks again!

  4. J1 just let me go, and allows me to enroll into COBRA.
    Can I enroll into COBRA, and also HSA plans with J2 and J3?

  5. I have J1 and already enrolled in their medical and dental benefits. J2 is requiring I send them a copy of my insurance card if I am declining coverage. Should I be worried? Will the be able to verify that I am working for J1? I thought it was as simple as “nope I don’t want coverage” so I’m not sure why HR wants a copy of my current insurance card. What are they fishing for? Or maybe I’m just overthinking hahaha. Anybody with a similar experience?

    1. Hi, insurance broker here. They need to have documentation in case they are ever audited or if an employee later tries to state they weren’t offered coverage. Ties back to the plan requirements that it be offered equally to everyone. Also if they have more than 50 employees, ACA requires they provide minimum coverage to every employee. Typically they can’t really use your insurance card to verify J2 since HIPAA will not allow the insurance carrier to provide any info to J1 about who the insured is, plan details etc.

  6. I’m being offered a contract j2 through a contacting agency, working for the insurance company I happen to have my medical insurance through for j1. J1 is not an insurance company but in a medical records field. Will j2 identify my j1 since I’m in a database as insured by them for another employer?

  7. Can I opt to not be double insured and just receive that money into my paycheck (that they’d be paying out to insurance)?

  8. Q1) Can we have family insurance with one job and an individual from another? Will there be any red flags?
    Q2) Coordination of benefits, do we need to do anything manually or is it taken care of automatically? Will the employer be involved anyway?

  9. I’ve got 2 full-time salaried jobs that each provide free insurance. I’m being asked by one of the insurance companies to do the “Coordination of benefits” thing. How do I designate which is primary and which is secondary. Both jobs are “primary” to me although one of them has a lower deductible and better coverage. Or do the insurance companies decide? I mostly just don’t want to get caught. It’s kinda like having 2 girlfriends 😉

    1. You don’t determine COB which is primary or secondary. The billing folks and health providers decide amongst them — I know, it’s kind of a mystery.

  10. The Obama federal tax penalty for not enrolling in health insurance was eliminated in 2019 because of changes made by the Trump Administration. However, some states such as NJ, CA, DC, RI and MA have their own state penalties.

  11. Hello, this article came right on time. I’ve been working as a FT consultant at J1 for eight months. I recently started a FT salaried position at J2 and enrolled their insurance since it’s better and cheaper. I just found out that they use the same insurer. Will I be safe?

    1. I’ve had the same insurance with aetna. Once as a contractor, and again as a full time. I don’t think they know of eachother, except at the point of contact for you as a user when you log on. They both existed at the same time, with two different actual plans.

  12. I have insurance with J1. J2 just started offering insurance at almost no cost to employees. My concern is the new insurance being offered is the same carrier. How does that work? will the carrier reject or come back to me that I already have active coverage through them? I want to have both policies as eventually I will leave one of these jobs soon, just not sure which..
    Thoughts? ideas? Worried here.

  13. I have insurance through J1 and will be accepting J2 soon. I plan to quit J1 after about 6 months or so, so I need J2’s health insurance in the long run. If I have Kaiser as my medical insurance for both, will either job find out since it’s the same insurer?

  14. So I currently have two full time jobs and health insurance through both. Should I be doing a coordination of benefits or should I just put down the one that gives me the best coverage?

    1. Definitely save yourself some money and get the second insurance to cover the rest of your claims. Yes — definitely do coordination of benefits, just tell the billing person at your health provider(s).

  15. I’m new here and am about to take on J2… was wondering what this means for my health insurance. I’m currently consulting with J1 and have mediocre health insurance (not an HDHP). I’m getting an offer letter for J2 and would like J2 to be my Primary, long term employer. So I’d like to go on the HDHP provided by J2 (they match an HSA) and quit the health plan I’m currently on with J1. Is this doable? Do I need to provide documentation of a life event? I don’t want them to know that I’m getting a second job, but I’d like to contribute to the matching HSA provided at J2. I’m worried that I can’t do this because I’m not on a HDHP with J1.

    1. Just tell your J1 you want to disenroll to switch over to a partner’s plan as they got a new job. You just can’t be on a non-HDHP together with an HSA-eligible HDHP. So if J2 also has a PPO or some other low deductible plan, I’d just go for that.

    2. As it currently stands you are correct, you cannot contribute to an HSA even if covered by an HSA-eligible HDHP at J2 because the PPO at J1 is disqualifying.

      You will need to drop the PPO at J1 before you can contribute to the HSA.
      Its arguably your prerogative to stop payment for something you no longer want so each employer handles dropping differently. Some will allow you just to drop, others will require proof of alternative coverage so you’ll want to check with your employer to see how they handle wanting to drop your coverage. The path of least resistance is likely to be as Isaac said, indicate you may be eligible for alternative coverage and you’re trying to determine the if you can drop coverage with them and what documentation they will require.

      Gaining alternative coverage is in a bit of a grey area as its not technically a qualifying life event, normally when a spouse changes jobs, the qualifying life event that enables a special enrollment (or disenrollment in this case) is the loss of coverage your spouse has when moving from J1 to J2, so ultimately, you may be stuck in the PPO with J1 for the year.

      Also keep in mind that your maximum combined employee+employer contribution to your HSA for 2022 ($3650) will be reduced for every month you are covered by the HSA-ineligible PPO health coverage of J1. The IRS does this by calendar months so if you’re covered by J1’s plan until February 1, you’ll be technically be disqualified from contributing to the HSA for the entire month of February. That doesn’t mean you or your J2 employer cant make a contribution at all in the month of February, it just means the maximum total contribution between both you and your employer at the end of the year cannot be more than $3041.66 ($3650 max contribution for 2022 divided by 12 months in the year multiplied by the 10 months in which you were covered only by HSA-eligible health plans and thus permitted to contribute to the HSA).

      Because of this reduction in savings, there becomes a point at which going through the process of changing coverages at J1 so you can get the employer HSA contribution from J2 may be an exercise in over-optimization. Assuming a dollar-for-dollar match up to the maximum, the maximum employer contribution will be $1825 this year. Over 30 years at 7% returns this amounts to roughly 20k more available in retirement, about 5k on the growth in your $1825 contribution (vs making a similar contribution to a taxable account) and 15k in the employer contribution plus tax. That’s less than $1k more per year and against a $1M retirement nest egg a only a difference of 2%.

  16. I am in a position to hold two jobs and have few questions about health insurance matters. Currently I have a HDHP with HSA at J1. The new job starts in February and has a choice of PPO or HDHP. Either option is cheaper than what I pay now. I plan to keep both jobs for 5-6 months and then quit J1.

    I that situation, should I enroll in HDPD in the new job and keep HDPD at the old one or get a PPO at the new one and try “my spouse got a job and insurance” with J1 to drop HDPD there? Will they require any proof?
    Ideally I’d like to keep both insurances just in case I quit J2 instead of J1 as planned.

    1. Which job is your keeper? When it comes to insurance, get the more conservative safest plan that provides more than what you think your family will need. If keeping both insurances at each job makes sense, then do that. You can afford it; you’ve two jobs!

      We really need to stop the cost-optimizing mindset and instead think BIG by growing the pie (more jobs, incomes, etc.), and not get too narrowly focused on how to divvy up the pie (lowering the in-between the line costs/expenses).

    2. Hey Issac,

      I am not trying to cost-optimize but rather choose a correct path from the IRS perspective. I understand that having PPO and HSA is prohibited but having to HDHPs is ok, correct?
      If I quit J1 as planned I won’t be able to have HSA at J2 until open enrollment starts, correct?
      I plan to do all this for the first time and feel a bit overwhelmed. Not even sure which job I would keep after 5-6 months…

    3. From IRS, you cannot have a PPO and an HSA-eligible HDHP at the same time. You can, however, have two HSA-eligible HDHPs, but can’t contribute over the universal HSA limit across the two plans, if that makes sense. To add to it all, not all HDHP are considered HSA-eligible. I don’t make the rules…just play by them.

    4. @Mickey, just a small clarification on Issac’s comment that “you cannot have a PPO and an HSA-eligible HDHP at the same time.”

      We’re really talking about 3 different types of accounts:
      A) An HSA-eligible HDHP – This is a High-Deductible Health Plan that has been pre-qualified by your employer as being eligible for HSA contributions.
      B) A PPO – This is a Preferred Provider Plan that is ineligible for HSA contributions
      C) An HSA – This is a Health Savings Account to which you contribute pre-tax dollars.

      The IRS does not say you cannot have an HSA-eligible HDHP and PPO at the same time. What they do say is that you cannot contribute to an HSA while having a health plan that is ineligible for HSA contributions. Just because you have a HDHP that is HSA-eligible doesn’t mean you have to have an HSA or make contributions to said HSA, they are separate entities.

      So if you want to switch to a PPO with J2, sign up for the PPO. You’ll be disqualified from contributing to the HSA in the month coverage from the PPO starts so you’ll need to go to J1 and make an election change for the HSA payroll deduction to stop further contributions. Unlike other healthcare election changes, changing an HSA contribution does not require proof or justification.

      The challenge here is going to be that you’re only eligible for the HSA for the part of the year where you are covered by only the HDHP plan. This does mean that you may overcontribute to the HSA if your combined employee+employer contribution for the year is greater than $304.17 (3650/12) per month times the number of months you were eligible to participate in the HSA. This does mean you may have to take a taxable withdraw of funds from the account and pay taxes + penalties on that overcontribution at the end of the year. That could be painful come tax time:

      Assuming you make a full years worth of individual contributions at $3650 (family plans limits are doubled and could be up to $7300) and are ineligible for the entire year, at the top nominal tax bracket of 37%, you’d have another $1350 due in taxes plus the 20% penalty of $730 for a total due of $2080 meaning you’ll only walk away with $1570 or 43% of that $3650. Depending on your overall tax situation for the year that balance due may also be enough to put you over the edge and trigger further underpayment tax penalties and interest on your total tax bill assuming the amount you paid through withholdings and estimated taxes is less than 90% of the total tax due for the year or less than 100% of the previous year’s taxes whichever is smaller.

      Or maybe its not so painful… Assuming that $3650 didn’t come out of your pay, even after all the taxes and penalties, its still essentially found money.

      Ultimately, I’m just some guy on the internet so as always you should consult Pub 969 your self and with a tax consultant before taking my advice and as you can see this gets fairly complex pretty quick so Isaac’s general advice to KISS is spot on.

  17. This is a great article because I didn’t know there was others like me. So happy to find this community. So here my issue…

    I have J1 for over a year now.. remote and insured myself under individual only as their family plan was SUPER expensive and not that great (I am a single mom, head of household with a teenage boy) and then I was hired for a J2 full time as well in another state. I relocated for it, changed address (the J1 company the whole staff is fully remote) and now J2 is also offering me great insurance which is what I’d to have for my son (previously we had Medicaid in NJ (which I disqualified for eventually but my son was still duly covered) but we moved now to Florida for J2. I am so confused as to what to do. He has braces which he’s almost done with through Medicaid and I’m considering flying back to NJ so he can properly finish the process as he is insured until April 2022.

    What do I do? And I’m also curious about the HSA stuff. I didn’t enroll in J1 so can I enroll in J2 and do I remove my son from Medicaid and if so, what about his braces?

    1. Sounds like over-optimizing here. You’ve two, I repeat, two jobs and two incomes. Use that money wisely to ensure your son is properly insured and taken care of. And spend that energy on growing your income than trying to cost-optimize. Don’t be penny wise and pound foolish. Just my opinion here.

  18. After having worked for some time in HR, it is a major gamble if you think you won’t be asked to provide proof of spousal insurance for the qualifying event. It is a general policy at all employers I have worked for to request this information as documentation for the event.

    Regarding dual insurance at the same insurer, that is much less of a red flag believe it or not. I was dual insured by the same insurer for over a year and didn’t even know it as the rep at the insurance company didn’t process the cancellation even though I wasn’t paying any longer for it! I went back and forth numerous times trying to get it straightened out. It is easier to get lost in the shuffle with insurance rather than an employer who knows you much better. Both of the plans I were in were high deductible plans and I heard nothing from IRS on either of them and as I mentioned, it went on for a year shockingly!

    1. Since you’re experienced in HR, perhaps you know the answer to this question… I already have health insurance through J1. If I take a position at J2 and decline their insurance, is there any way they can find out about my already existing coverage through J1?

    2. WonderMan: no. And they won’t look for it, either. You could have coverage through the VA, tricare, Medicare, medicaid, a spouse with benefits. The only thing they want to see some documentation on is qualifying life events that enable you to enroll outside of open enrollment.

    3. HR from J2 is asking me to provide a card to show i have proof of coverage since i’m opting out. i am a little bit paranoid. Can i just send them an old card which is inactive? will they check? Or should i send them the card i have from J1.

  19. Darn I was just thinking for the tax saving do half and half for family HSA. So $3600 each plan.
    But even, from Peter’s clarification might be best to get 100% from job 1 and do single from job 2.

  20. you have 2 full time jobs, which means you have 2 healthcare/dental/vision/life insurances, will you be caught if you claim your medical/life insurance?

    1. If youre claiming life insurance, your dead (or dismembered) so who cares?
      If youre claiming benefits under your medical insurance, ultimately, your employer should have no involvement in your medical situation and medical claims, even with an employer self-funded health-plan they bring in a 3rd party administrator and mainstream insurance organization to negotiate rates and manage claims. In addition, as a explained in the article talking about how coordination of benefits works, there’s no reason why you cant have 2 insurances and the fact that one knows about the other doesn’t mean they know why you are dual covered so even if your employer were for some reason involved, there would be no reason this would lead to being caught.

  21. This is a great article.

    For the Overemployed in Canada, I understand government health insurance through each province of territory is for all citizens and permanent residents. There also are no deductibles or co-pays.

    However, the sales tax in Canadian jurisdictions is higher than in most states.

    For additional health benefits (i.e. dental and prescription plans) for Canadian Overemployed, I understand the best approach is to say “no thank you” and have just one plan with the primary employer for dental and related coverage.

    Another approach is to, if you have a significant other, have your supplementary coverage through your partner’s plan .and advise all employer of this situation. But only do so if it is true.

    Giving a knowingly false declaration like that is an act of commission that can be problematic If you do not have a significant other and make such a false declaration “i am on my husband’s plan” and employer finds out thre is no husband, then the employer can think “if X is lying about having a significant other for supplementary health coverage, what other lies have been told.

  22. Hey guys. Say you decide to keep the better insurance with Job A and forgo Job B’s insurance but then decide to quit Job A to find a replacement for that, how do you get insurance coverage in the interim under Job B? Commence it under “life changing circumstances”? And if so, how do you prove that? I was think of having the insurance company simply write me a letter to say that I’ve lost coverage under that plan but keep it generic and not mention it’s an employer plan. I dunno. Any advice?

    1. Do you have a spouse or qualify for parents’ coverage? If so, you can say you lost coverage that way. Or just buy health insurance in the public marketplace as gap stopper until you can enroll in J2’s when enrollment opens up.

    2. Question! I’m working 2 jobs and took health insurance for Job A. I am going to leave that job and take insurance from Job B during their open enrollment period. I just found out that it is the same insurance in the same state (both companies based in same city/state).

      If I resign from Job A in October and take Job B’s plan in November, will my employees be notified that I was employed at another company?

      My concern is that if they do would I will be terminated.


    3. Isaac #2 – there shouldn’t be any feedback loop back from insurer to employer–even if they are “self” insured, they are still going to use an insurance company as a “third party administrator” to pay and manage health benefits, because your (and your family’s) healthcare claims are protected health information. As such, your employer >can’t< know any of that. (This is a U.S. answer)

  23. Your interpretation of Pub 969 regarding multiple HDHP plans may be flawed.
    Understanding that the tax advantages of a HSA is designed to offset the high-deductible expense, the provisions for “additional health insurance” are traditionally held to be “additional disqualifying health coverage” by coverage not defined by the IRS as a “high deductible health plan” and would reimburse or pay for medical expenses prior to reaching the deductible amount under the HDHP plan.

    That is to say you cant be enrolled in a HDHP at employer 1 and a PPO at employer 2 and still contribute to an HSA with employer #1 because insurance #2 is a disqualifying health plan and would “coordinate benefits” and offer reimbursement or payment before the deductible of the HDHP is reached. This would be the same as enrolling yourself in an HDHP plan but then getting a PPO through your spouse.

    However if you enroll in a qualified HDHP at both employers, there is no reimbursement available until the deductible is reached in at least 1 of the 2 plans and there are no additional cost savings available through coordination of benefits until the deductible is reached under both plans. This is a typical scenario when you and your spouse are both covered by each other’s HDHP plans, thus having “dual coverage” and still being eligible to contribute to an HSA.

    The downside to being dual enrolled in 2 HDHP plans is that they generally do cost you something and many employers these days are also offering additional pay if you decline all health/dental/vision coverage. The upside is that you can capture multiple HSA employer contributions (subject to the annual limit which could get sticky if the combined employer HSA contributions exceed the limit) and you offset the risk of going uninsured if you quit, get fired or get caught at either of your jobs. Coordination of benefits after reaching the deductible may also reduce the overall cost and there may be other benefits depending on the exact details of the plan and costs (.e.g. Employer 1 offers a HDHP with a lower deductible and lower max-out-of-pocket than employer 2’s HDHP plan but the “family coverage” is considerably more expensive with employer 1. Electing “individual” with employer 1 and designating that insurance as primary and electing “family” and covering your “other insured/covered” spouse would allow you and your spouse to contribute to the HSA up to the “family” maximum provided your spouse isn’t contributing to an FSA or HRA; since the HSA funds roll over and the maximum contribution is greater than the FSA, this is generally a more advantageous tax scenario).

    “You can be covered under two HDHPs, though. If your employer and your spouse’s employer both offer HDHPs, you can opt for double coverage and still contribute to your HSA”
    Source: hsastore (dot) com (forward slash) learn-coverage-hsa-contribute (dot) html

    This is also why an HSA can generally only be contributed to up to age 65 as Medicare automatically kicks in and is a disqualifying additional coverage.

    While you can delay enrollment in Medicare Part A, you generally only want to do so under specific circumstances (e.g. still working for an employer with more than 20 employees and covered by a plan at work) to avoid late enrollment penalties in Medicare Part B and even then, due to the complexities with deferring and then getting enrolled, it maybe easier to just take the auto-enrollment and stop contributing to your HSA at 65.

    Note that your article here indicates you can only use HSA funds “for medical expenses until you reach 65” which is definitely incorrect. Its your money and you can use the funds, tax free, for qualified medical expenses at any time, even beyond age 65.

    1. Hey Peter, thanks for this great explanation. I’ve revised the HSA & over age 65 comment to be more accurate. Appreciate the feedback and clarification on double HDHPs. When in doubt, I always lean towards KISS and being more conservative on healthcare. Both HSA and FSA touch the tax code, so game it with care — they’re designed for the one employee, one employer world.

  24. Hello!
    I have “invisible” disabilities that I do not share with the potential employer during the hiring process. I figure the HSAs would not work for me based on the article. Is there any advice you would give me? What should I keep in mind and what should I look for/prioritize?


    1. Hi! Without knowing all the details of your situation, I’d just make sure you’re properly insured (most employers offer a premium, better, and just good enough type of plans), Pay particular attention to each employer’s short-term and long-term disabilities policy. Some offer 100% STD and 67% LTD, which is quite generous.

  25. Excellent article! When I first started working two full-time gigs, I opted to have double coverage in the event that I needed to drop one job I was guaranteed to be covered. However, the “qualifying events” are not as difficult to qualify for as you might think. When I got tired of paying $1k a month for medical coverage through my original employer, I just called them and told them my spouse started working and now has our family covered through her employer. There was no proof required. I would assume the reverse is true as well, if I needed to regain coverage I could have called and just said my spouse was let go and we lost our coverage.

    1. That’s good to know! Mine were quite stringent. Looks like might be employer/benefits administrator dependent. I find the “open enrollment” quite archaic and annoying. It’s all tailored to negative use cases like someone trying to “game” the insurance companies and get coverage before a “big” medical event.

    2. This is the exact information I was looking for. I plan to keep my health insurance only with J1 to avoid paying multiple premiums, but if I decided to leave that job or get let go for some reason, how difficult would it be to then get insurance under J2 because of a “qualifying event”.

      Just curious, which healthcare provider were you working with?

    3. Henry — it’s not the health insurance company that matters in this case, but the benefits administrator (all the companies I have worked for farm benefits enrollment work out to a third party). The benefits administrator will be asking for and evaluating your qualifying life event documentation (under the direction of your company, in theory, but in practice the benefits administrator probable does it the way they always do it).

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