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After landing a new job, I opened a health savings account (HSA) in February 2019. I decided to contribute $1 of my pay per pay period to my HSA. However, I can change my contribution amount at any time.

Recently I've been advised by my endodontist that a $10,000 operation is in order. If I'm having the operation in 5 pay periods, can I now start funneling in $2,000 per pay period into my HSA, enabling me to pay the bill in full through my HSA debit card, and expect to have $10,000 less in taxable income? Or, does the IRS lay out time restrictions for a scenario like this (in which case I can postpone my operation to next year and have the same result).

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    How does the $10,000 cost fit in with your deductible, co-insurance, and out of pocket maximum? Is the $10,000 what they charge or is it the negotiated rate with the insurance company? – mhoran_psprep Jul 2 at 10:18
  • This is an important point. The $10,000 is the fee I owe after my dental insurance (separate from my medical) pays their share. – Sean Daley Jul 2 at 14:18
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    how is that an insurance if you are left with 10000$ to pay after them? – njzk2 Jul 3 at 2:43
  • Depending on the particular operation, insurance will minimally cover. This is common with tooth implants. – Sean Daley Jul 3 at 2:52
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There's an annual contribution limit, for 2019 it is $3,500 single/$7,000 family. Otherwise, it's fine to match future contributions to prior or planned qualifying expenses so long as the account was established before the expenses were incurred.

There is no deadline for reimbursement, so if you have the procedure done now and pay out of pocket, you can contribute the annual maximum for a while and get reimbursed later.

The ideal scenario from a tax perspective is contributing the annual maximum to your HSA, paying all bills out of pocket and letting the funds grow tax-free for years before requesting reimbursement on all the expenses you paid out of pocket.

The ideal isn't practical for everyone, it requires saving receipts, paying attention to IRS rule-changes, having an HSA with good investment options, and being able to cover the medical expenses out of pocket.

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    Just a note to add onto this, the contribution limit is personal and employer contributions combined. So if your employer is contributing funds you need to deduct that from the limit to know what you can contribute. – user1723699 Jul 2 at 13:59
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    It's been a while since I worked for a company with HSA, but when I did I don't think there was any rollover from year to year, it was "use it or lose it". Has that changed? – Barmar Jul 2 at 14:53
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    @Barmar FSA's have the use it or lose it feature, HSA's persist. – Hart CO Jul 2 at 14:54
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    Ahh, that must have been what we had. Like I said, it's been a while. – Barmar Jul 2 at 15:08
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In addition to other answers: you do not have to pay for medical service in full in one lump sum. Often medical service providers agree on an interest-free installment plan with small monthly payments. And you can pay the installments from your HSA while pumping funds in there every paycheck.

There is a yearly limit to how much one can contribute into HSA. It's a tax year, so per-paycheck contributions need to be set to hit the limit by the end of the year if you start contributing right now. And then corrected down in the following year.

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You should check with your employer to see if contibuting evenly through the year would maximize the employer match to your contribution. If that is the case, next year then you will have both reduced your taxable income and gotten a little bit more from the employer match.

The first reply post sounds right, check your contribution limit maximums.

Another option, You can pay for the treatment now, with credit card and reimburse yourself via the hsa in the future when your account balance reaches 10000. You would then be refunding yourself in pretax dollars.

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    Putting $10k on a credit card and letting the balance ride for years until the HSA balance gets that high will cost a lot in interest. It would almost certainly be cheaper to work out a financing plan with the orthodontist, especially if the entire HSA situation is explained. – Upper_Case Jul 2 at 15:37
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    That is a good point. I assumed the poster could pay off that balance. adding to what others have mentioned, paying the installment payments on credit card, while waiting for HSA balance to grow. – akyeung Jul 2 at 18:14

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