How to reimburse yourself from an HSA

My first health savings account reimbursement arrived in just two days.

Photo by Nappy on Unsplash

Last March, I wrote about finally opening a health savings account and committing to it in a way I never had before.

I framed it as a long-term play. A freedom fund. Something future me would appreciate, even if present me felt a little pinched every pay period.

At the time, the HSA was still theoretical.

I understood the tax advantages. I liked the investing component. I enjoyed watching the balance grow. But there was one part of the experience I hadn’t tested yet, and it’s the part that tends to make people uneasy.

Getting your money back.

That moment arrived recently in the form of a $4,273 root canal bill.

Not a small expense. Not something I could shrug off.

Exactly the kind of medical cost an HSA is designed to handle, and exactly the kind of moment where friction would reveal itself if it existed.

I submitted the reimbursement on Dec. 10.

The money hit my bank account on Dec. 12.

Two days.

That was it. No paperwork maze. No phone calls. No second-guessing whether I clicked the right thing.

The speed alone caught me off guard, mostly because I’d just assumed the process would be clunky by default.

Here’s what it actually looked like.

I logged into my HSA app. I clicked “reimburse myself.” I selected the account. I entered the amount. I linked my bank account, which took maybe a minute. I chose the transfer destination. I hit submit. Then I uploaded a photo of the receipt using my phone’s camera.

Eight steps. All intuitive. All done from my kitchen table.

That was the entire process.

This was my first reimbursement since launching the HSA in January 2024, and it came nearly two years after I committed to the strategy in December 2023 of paying medical expenses out of pocket whenever possible and letting the account grow. That patience mattered.

Before my reimbursement was processed, my HSA had grown to nearly $15,000. More than $5,000 was available to spend on medical expenses. Another $9,000 and change remained invested and compounding in the background.

Reimbursing myself for a major expense didn’t derail the plan. It simply validated it.

That’s the part I don’t think gets emphasized enough when people talk about HSAs. They’re not just powerful in theory or on a spreadsheet.

They’re practical. Liquid. Fast. When something expensive and unavoidable happens, the money is there, and accessing it doesn’t feel like a penalty.

If anything, the hardest part of this entire process wasn’t the reimbursement. It was getting started.

It was committing to smaller paychecks and trusting that future flexibility was worth it.

It was believing the system would work as advertised.

Now I know it does.