How Do I Categorize Stock Shares Donated to Charity?

I assume that the shares donated were held long term and that you want your Quicken accounting to show the same results as it will on your income tax return, i.e., you don't have the shares anymore but you have a charitable donation in the amount of the fair market value at the date of the donation.

I can tell you how to make this work in the Windows version and presumably there's some similar facility in the Mac version.

The first thing I'd do is a "Removed" action in Quicken on the date of the gift.  Quicken requires the name of the security and the number of shares.  If you have more than one lot of the fund Quicken asks for the lot or lots to be removed.  In the Windows version you won't see any offsetting Account or Category used; it looks like an one-sided accounting entry, but it's not, really.  If you run a Net Worth report immediately after this transaction is entered you'll see a decrease in your Investment Account and a reduction of your Net Worth by a similar amount.  Effectively it's a

Debit (decrease) to Net Worth and a

Credit (decrease) to the Investment Account

The next entry in the Windows version would be an Xin (Transfer cash in) action for the fair market value of the shares gifted.  Again, this would look like a one-sided entry, this time increasing the value of the Investment Account and your Net Worth.

The final entry would be a MiscExp (Miscellaneous Expense) action for the same dollar amount as the previous entry with a Category of "Charity".

Actually that final entry, in Windows, could really be a variety of actions; one might be to "transfer" the money out of the investment Account to the checking Account, and then you could expense that amount there.