Pay as much as possible directly from your HSA Account. Categorize these
transactions in your Quicken HSA register as MEDICAL:HSA PAID

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How to categorize a transaction that is an HSA-submittable expense, but you
paid it using a different bank account or credit card:

If you might submit a claim in the future (you have the rest of your life to
decide, and some people like to wait and see what you might deduct on Schedule
A this year)):

Category is [HSA SUBMITTABLE] -- This is an asset account and will record as a
transfer.

Sales Tax is submittable!

When you are ready to submit a claim for multiple transactions,

Go to HSA SUBMITTABLE account register.

For each transaction to be submitted:

Go to matching transfer in the account where the expense was recorded -- hotkey
is CTRL X. This is important. If you edit the transaction in HSA Submittable,
the edits will not appear in the original transaction.

Change category to MEDICAL: HSA REIMBURSED.

Enter in Memo field: Claim Submitted, Date.

Enter transaction representing the claim in Quicken HSA account register:

Date = date claim was submitted
Payee = CLAIM SUBMITTED
Category = [BANK ACCOUNT] that will receive the claim payment
Amount = total amount of the claim

Go to your HSA online and file the claim.

When the claim is paid, it will appear in your Quicken downloads and will match
the transfer you have already recorded.

If you are not going to submit a claim to your HSA  for this transaction, but
it qualifies for a tax deduction at the end of the year, categorize as
MEDICAL:SCHEDULE A