How do I enter a transaction with multiple accounts?

In my way of thinking, it is two transactions against two different Quicken accounts, so it should be entered with one transaction in each account.

Anything you do to combine the two transactions into a single entry, will take more time and make for a confusing mess using splits which won't properly categorize the purchase.

(I deleted my post since it is inaccurate.)

Oops! I misread your original post. I guess I shouldn't be posting things in Community while I'm multi-tasking with reviewing my 2025 Medicare plan options (my Part D plan is dropping coverage for my highest cost med….ugh!!!). I've deleted my post above because your suggestion is a very good one…similar in structure to how I manage my monthly SS deposits and IRA distributions.

Sorry for the mess up on this one, folks.

I hadn't thought of that but, yes, there are some unique tax impacts here that Quicken is just not really set up to deal with properly.

HSAs are tax advantaged accounts that are funded with pre-tax dollars and distributions are tax-free. So, it's kind of like a hybrid tax-deferred IRA and a tax-exempt Roth IRA account (for healthcare expenses instead of for retirement) all rolled into one. It blends the best of both the IRA and Roth IRA worlds.

However, HSA medical expenses are not tax deductible so they cannot be included in Schedule A as such.

Quicken does not have a HSA account type so I can understand why so many users are displeased about that.

In light of all this, it would seem that the split categories option @UKR and I discussed above will likely cause tax data to be captured incorrectly. That is because the HSA expense side of the payment should not be captured at all as a tax deductible expense but assuming that the category used is the default category for a medical expense it will be doing just that. And if it is not using the default medical expense category, then the credit card side of the expense would not be capturing the tax deduction since it is a transfer category instead of the default medical expense category.

To better capture the dollars in the tax reports and tax planner, then I think your suggestion (one transaction in the HSA account and one transaction in the credit card account) might be the better option. But that assumes that the HSA expense category is not associated with the tax line item for medical expenses and the credit card expense category is associated with the correct tax line item for medical expense(s).

Then it begs the question: What is the best workaround way to set up a HSA account in Quicken so that it properly captures the HSA tax advantages? My initial thought is to set up the account as an IRA account or a Roth IRA account, set it to "Tax Deferred" and give it a HSA account name. Then change the Tax Schedule for transfers in to "Form 1040:IRA contribution, self (or spouse)" and change transfers out to "1099-R:Total IRA Gross distrib." It's not perfect but Quicken should then capture HSA account contributions as pre-tax deductions so it will reduce taxable income. And Quicken should then capture the HSA distributions as tax-free.

But this is all moot if @musicalSaranader is not using Quicken to capture, report and plan taxes. If they are using Quicken simply as an income/expense and budgeting tool then the split categories option might be best because it is so easy to use.