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While there is no time limit for requesting reimbursements from an HSA, they must be incurred after the HSA was established (https://www.irs.gov/irb/2004-33_IRB) .

I normally pay for my medical expenses out of pocket, and instead save the receipt. This gives me the option to treat my HSA as an IRA (if it makes it to retirement age) OR as an emergency fund as I have been savings my receipts through the years.

Delaying reimbursements from an HSA and savings receipts to be reimbursed at a future time comes into a problem if you change custodians/employers.

Would I have to request reimbursements for all my receipts prior to changing custodians?

Or can I transfer all my assets to the new custodian and submit receipts to the new custodian from expenses incurred during the previous custodian?

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When you roll an old HSA into a new HSA it inherits the established date of the older HSA.

From Publication 969 (2016), Health Savings Accounts and Other Tax-Favored Health Plans:

State law determines when an HSA is established. An HSA that is funded by amounts rolled over from an Archer MSA or another HSA is established on the date the prior account was established.

Rules may vary by state as to when your first HSA was officially established, but subsequent accounts inherit that date if rolling funds over. Even though it's clearly stated in IRS documentation, I'd probably put in a call to a prospective provider to ensure that there would be no snags on their end. It's also worth noting that the current withdrawal period is not set in stone, so make sure you're keeping up on rule changes if piling up substantial amounts for later withdrawal.

Finally, you don't have to use your employer's HSA provider, you can transfer funds annually to your preferred provider. This is important if your employer has chosen a provider with poor investment options.

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    Nice answer. Perhaps keeping some statements from prior HSA accounts with the receipts would be a good idea too so that account start and end dates can be proven if needed. Regarding your last paragraph, I'd like to emphasize that (like you said), you should put the funds into the employer's HSA and then transfer to them to your preferred provider as you suggested, rather than putting them directly into your preferred HSA provider. This way you can save on the FICA taxes.
    – TTT
    Sep 28, 2017 at 15:50

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