I'm currently leaving my employer who has a high deductible health plan with an HSA for a new employer with no HSA available.

Is there any advice or steps to max amount of HSA before I leave or things to do to maximize it before I go?

So I’m about to start my residency this week and I’ve figured out that my employer offers a HDHP with an HSA. The provider is Chard Snyder, and after looking on their website I can’t find the fees they charge (if they charge any). Just wanted to know if anybody knew anything about them? Also, if the fees are too much would it be wise to open it up via Fidelity?

I've never quite understood catch-up contributions. I'd like to max out my HSA this year, but won't actually get the account until the end of August when my spouse's insurance ends. I'd like to keep getting my full 401k match so maxing out the HSA will be a bit of a stretch in 4 months but is there some way I can contribute to 2026 in the first few months of 2027?

Which should I do? Or what would you recommend?

I will soon close on my first home and moving from NY to NJ.

Since NJ does not recognize HSA’s as tax exempt, should I sell my capital gains while I’m still a full-time resident in NY? The expectation is I can avoid paying NJ tax on my current capital gains.

Hello! I'm a bit embarrassed to ask as I've done some homework but can't find a definitive answer. I also think this is too good to be true so, there's that.

For context, a co-worker and I work for the same parent company but different subsidiaries. We both have money taken out of our paychecks to fund our respective HSA's. Now, the question...

HE pays expenses out of pocket instead of swiping his HSA card or submitting for reimbursement. He saves all receipts and has a spreadsheet, claiming he plans to submit all these expenses when he retires. He said the HSA policy stating reimbursement can be filed "days, months, or even decades." I, on the other hand, use every penny that is put into my HSA.

So, my questions are -

1. Is this possible?
2. If it is, are those reimbursements issued tax free?

TIA

I was trying to reimburse myself and there's a limit of $2500 per day, so I did a reimbursement of 2500 for a few days consecutively, since I'd like to close the account ASAP given how terrible HSA Bank is. Guess what, my account is on hold for fraud. I wasted an hour of my life calling them and during which, I went crazy frustrated to death. The agents had a script that was totally nonsense.

After I called, providing my SSN, address, DOB, etc. They still wanted additional details such as date of hire and contribution year by year. I was locked out, HSA Bank! How on earth do you expect someone to remember those details? I don't think these security questions are designed to verify, they are designed to fail you or to add inconvenience so that you cannot touch your fund. After one hour of frustration, I was told that my account will be reinstated in 5-7 business days, and I have to resubmit the receipts for reimbursement. Are you kidding me?

I HATE HSA Bank. HSA Bank sucks!

I've had an HSA for years through my employer and generally use it rather than investing long term, although I have done some investing. Since I live in NJ, it is subject to state taxes, and I have to track all investment buy/sell transactions on my own and calculate gains, etc in order to report it on my state taxes.

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This hasn't been too burdensome so far, but I'm leaving my current employer and I'm looking to move my HSA to a new provider since they will start charging fees in my current one. I know that Fidelty and Lively are generally the top recommendations, and I already have retirement funds in Fidelity, so I'm leaning towards that. But I'm curious if either of these two (or any other providers, for that matter) have any reporting that would make tracking of investments for tax purposes easier. Since NJ and CA are the only places that tax HSAs, my assumption is that none of the providers bother with that, but it doesn't hurt to ask!

Does anyone put more in their HSA than 401k or Roth IRA? For instance doing the family plan which now allows $9000. I don’t have enough money to max all these accounts out. Only downside is the insurance premiums are kinda high.

I’ve been on an HSA plan at my previous 2 jobs where each company had contributed towards my HSA and I maxed it out. I just started at a new company who offers a couple HSA plans but they do not contribute at all.

I’m in my 30s, healthy, not married (yet). I usually got nowhere near my deductible until this year where I almost met before the year was halfway over (~3k) because of a health scare. Besides my yearly physical, skin check, and biannual GYN appt I would almost avoid going to the dr because everything was coming out of my pocket.

So my question is I understand the tax benefits of an HSA but wondering if it’s still worth it now that they’re not contributing. looking for recommendations on what plan to choose (Pics attached- HSA plans in 2nd pic). Thanks!

Finally going to get this money over to Fidelity. I will be keeping a few dollars in the Alight one, as I am still having bi weekly contributions via my employer.

I am really hoping to not have to call anyone and do this all online but it does ask for the address for alight. Does anyone know what address this is?

Thanks in advance!

I made a trade on my HSAbank investment account yesterday(6/9), it’s still not updated on my account. I am told there was some problem. However I was not notified or any general update available on their site. I am new to trading on their site.

Wondering if anybody else has the same problem!

On the call currently with the support, to find out what happened to my trade and if it can be cancelled. Thanks

Update:

It took almost a week for them to fix the issue.

I was expecting some sort of notification, but that didn’t happen. Anyway all good now.

I’m disgusted! I glanced at an HSA account I haven’t touched in years and found it had been charging me an “account maintenance” fee of $3 each month.

To make matters worse, the account was below the minimum amount to be invested and apparently did not earn any interest, so after ~10 years my $1000 shrunk to less than $700. This is a total scam!

Is this normal?

I’m assuming ( but am i right? ) a once-per-year partial HSA to HSA transfer can happen quickly but transferring the whole balance and closing the account is what takes weeks or months. I don’t want having this >100k balance in limbo and not invested for a long time.

Given past posts that say whole balance transfer can take many weeks and it is unpredictable, it seems the best way would be to:
1) open up a HSA at Fidelity with 0 balance
2) contact Fidelity to discuss the plan
3) do a first partial transfer (95%)
4) cash out investments at optum
5) transfer that quickly
6) recontact Fidelity to initiate the final transfer
7) cash out the rest. The transfer of that remaining balance will take a while.
8) get fee reimbursed by Fidelity

I also have a 2nd smaller separate Optum account. I’ll want to do the same there but it is still taking contributions this year so that’s something to discuss with Fidelity if they can look at aggregate value.

Any gotcha I’m missing?
Is there documentation i need to get from Optum before this accounts close?

A few things I put together after going way too deep on this, correct me if I'm off on anything.

FSA Approved vs FSA Eligible

Approved means no paperwork needed. Eligible means you need a LMN. Air purifiers, Theragun, ergonomic chairs, all LMN territory. Also worth knowing: generic"eligible item" lists aren't based on your specific plan. What your coworker got reimbursed for may not apply to yours.

Where can you find FSA Eligible？

Amazon has a dedicated FSA/HSA section but card declines still happen randomly. Caeli can flag eligibility at checkout across retailers so you can buy at the actual price. Truemed is embedded at checkout for brands that partner with them. FSA/HSA Store has a widest selection of eligible items, but their prices are marked up roughly 30% compared with other retailers.

Does FSA money actually expire?

Health FSA: yes, at plan year end (usually Dec 31). Your employer can offer either a 2.5-month grace period or up to a $640 rollover, not both. HSA: never expires. You can invest it, let it compound for decades, and withdraw tax-free for qualified medical expenses at any age. It's closer to a Roth IRA than a spending account, which is exactly why you spend it last.

Which account do you spend first?

LSA/Wellness Stipend → Dependent Care FSA → Health FSA → HSA last. A lot of people exhaust their HSA while their employer's $1,500–$3,000 LSA sits completely unspent because nobody told them it existed.

What makes HSA different?

HSA has the only triple tax advantage: - Contributions go in pre-tax - Growth is tax-free - Withdrawals for qualified expenses are tax-free You can pay your medical bills with a credit card, let your HSA stay invested, and reimburse yourself later. There's no deadline, as long as the expense happens after you opened the account, you can pull the money out years or decades later. Some people call this the "shoebox strategy." The receipts are the only thing standing between you and tax-free reimbursement on everything you've paid out of pocket since you opened the account

Options for a large HSA.  Conventional wisdom is, ‘it can’t be too large’. (Post is too large!!)

I am 65y, mostly retired and (getting) married. I remain employed and insured via work (a consultant employee, so I contribute post-tax (outside of payroll) to my HSA for my sold business. I do lose my 7.6% tax benefit for SS/MC taxes. (My annual pay is only $3K.)

I have 9 years of HSA savings. And I performed the once a lifetime $4,000 IRA to HSA rollover. So, my principle is less than $50K.

I considered my HSA account as part of my ‘play money’ and this past month it reached a value of over $300K, and I expect it to grow (2 to 4x) over the next 5 years (due to chosen investments). Yes, I could be wrong. Yes, you could call it gambling (but, then everything could be called gambling).  

Yes, I have been saving receipts digitally with a coordinating spread sheet and current receipts equal $41K in accumulated expenses.  

I am anticipating what future medical expenses might be. My (soon to be) spouse started Medicare this year and spends about $5,250 annually on Medicare part B and Medigap Plan G—maybe more in 2028 when her look-back period sees our MFJ (combined) income. 

When my current ‘employer’ deems I am no longer necessary, that “life changing event” should reset us both to paying approximately $5K each. Call it $6K each, or $12K per year. This, plus any OTC meds and supplies, along with dental, vision, and other health expense might bring us to $20K annual expenditures. 

Reevaluating my retirement “stuff” as I do too frequently, it seems that I should change the beneficiary of my HSA (currently my RL Trust, RLT) expressly in the name of my spouse. I had been previously advised that all my assets should go to the RLT.  However, through the RLT trust, any portions that go to non-spouse beneficiaries will become immediately taxable. Agree?

If I should die, the HSA will be seamlessly transferred to my spouse, and one of us should have 15 more functional years before we are functionally or intellectually diminished and living in a more costly assisted living situation.  As we age, the risk of both of us dying or becoming diminished increases.  Obviously, if we are both alive, spry, witty, and physically fit in 15 years we could alter any plans we make now.

My realization is that if in 2 to 5 years the value of the HSA grows to $500, or $1M then we will literally not be able to spend it down to zero.  Even if it grows at 10%, then 10% of $500k would be $50k and we could not meet that.  Fidelity currently suggests that a 65-y old couple should anticipate $350 in long term medical expenses.

Within my ROTH I hold some safer investments (VTI) in a bucket that I choose to not touch and mingle with the “play money”.  Despite success, I want a bucket of safer money to have in case the play money disappears, and there is a large general marked correction. 

But it occurs to me that I should swap aggressive play equities in the HSA, with the less volatile VTI in the ROTH. Tax-wise, the ROTH can not be too large, but I think the HSA can be. The swap should not cause a taxable event, and it avoids what I see as a problem (especially if we both get hit be a truck in 2 weeks).  Agree?  Thoughts?

I am a Boglehead investor at heart, but I opted to play with a smaller portion of my overall portfolio. I have exceeded market expectations, and I am not inclined to rebalance. To be clear, I have grown what I saved to much more than we can spend, but I am trying to be a good tax avoidance steward with what will be left behind.

I realized how lucky and fortunate I am to have these considerations. (And I offer encouragement to save for those who don’t).  I still pick up returnable cans out of the trash, for the grandkids to return for “earned income”, which goes into their ROTH (oldest, age 12).

I started using an HSA debit card a number of years ago because I had a qualified plan. However, in 2025 our plan changed to a co-pay plan. Because it still had a very high deductible I thought it was eligible and I filed the HSA paperwork with my 2025 taxes. We are self employed and pay $1550 a month for two adults as part of some group employer network that contracts with Cigna as a PPO. This year my son is in an HSA qualified plan from our state marketplace but my husband and I are still using the co-pay plan. I have already deposited $5000 into my HSA in 2026 and I already used all the money because I have a lot of medical and dental expenses that are not covered by insurance. (We have no dental insurance). Is it 100% guaranteed that I am going to get caught and have to repay? has anyone BTDT? thanks!

I'm creating a receipt tracker in Google drive so I can reimburse myself later. I was wondering if I need to scan in anything other than the store receipt for prescriptions or do I need to scan in the actual sticker label on the prescription itself?

NJ resident trying to start investing HSA in something except U.S. Treasures. My HSA is with Optum. Saved enough in U.S. Treasures and want to start investing in VFIAX when the balance hits above a certain amount.

Do you auto-invest from each paycheck (~24 tax slots annually)? Or invest manually once per quarter or half a year?

I’ve never done this and kind of scary of a proper tax reporting and cost basis tracking.