Outlook 2003: How to group by flag AND sort by date?

Solution 1:

In the "Customize View" window, "Group By" should be "Flag Status" (as you have it shown). However, try changing "Sort" to "'Flag Status' then 'Received'", as shown below:

Outlook Grouping and Sorting

This makes it show up the way I think you're expecting it to (see below):

Mail sorted properly