How to download two funds in one brokerage account into two accounts in Quicken?

@ilyaz, Based on what you wrote, the Money Market and the Total Stock Market are the individual Vanguard index funds, right? Where in the past you chose to have one account for each fund, they are now part of the same single joint account. Am I understanding these correctly?

I also gather that you are manually downloading the data (exporting an OFX file) from Vanguard and then importing it into Quicken.

Let's take the IRA's out of this discussion since they are working for you as expected and focus only on the joint account. You wrote:

However, when I download the joint brokerage account from Vanguard, both the Money Market and the Total Stock Market go into the Money Market account in Quicken. How should I set up Quicken or Vanguard (or both) to download these two Vanguard accounts into two corresponding accounts in Quicken?

But they are not accounts, rather two funds held in a single joint account; do you agree or am I misunderstanding?

The question is: Why do you want to continue to have two accounts in Quicken for each fund where Vanguard already converted them into a single account? Isn't it better to have one account in Quicken (containing both funds) so that it matches exactly what Vanguard also has for you? To make a point, if you had fifty funds, would you really want to create fifty accounts in Quicken?

In my personal opinion I'd want Quicken to be a match with my online accounts, and in your case just rename the account from "Money Market account" to whatever you like, such as "Our Joint Account". But if you insist to keep the old model, you probably have to make manual adjustments in Quicken every time you download which would be a lot of work and result in balance and share mismatch errors - a maintenance nightmare.

Interesting enough I believe it was actually an option you could select at Vanguard that would put them in one account or one per security. But it wasn't easy to find. Years ago, when I did have Vanguard accounts, I had them setup to download all the securities for one account in a single Quicken account.