Your All Categories view (in the Tasks area) is your main context view. It shows you all tasks for all categories, grouped by category, including 1-1 contexts. Right click any category group header and select Collapse All to see all the headers. Click + next to the 1-1 context category header to expand it and see its tasks.

You must customize the Simple View before you can use it for this.

Check Sorting & Grouping

If you don’t see: 1) tasks grouped by Category, 2) High Priority at the top of each group, and 3) normal Priority sorted by Due Date, oldest at the top, then you probably clicked a column header. (Outlook breaks the sort when you do that.) To fix it:

  • Right click on one of the column titles (like Due Date).
  • Select Customize Current View… (Sometimes it appears as Customize…).
  • Click Sort.
  • Select the following sort order:
    • Sort items by Priority, Descending
    • Then by Due Date, Ascending
    • All others should be (none)
  • Click and drag the Categories column title to the Group By box.
  • Click the Group By box if needed to fix the Categories sort order.