[Toadling]

I think there's some confusion in terminology here. The most-recently-entered task (newest) gets sorted at the top, and the oldest gets sorted at the bottom. In other words, it does a descending sort by timestamp.

I think rdjong wants it to do an ascending sort by timestamp.

Unfortunately, I don't have an answer for you, rdjong. My impression is that Omni Group picked the sort algorithm they thought most people would find most useful. OmniFocus generally seems to sort from most recent to most distant (future or past), so I think it's consistent across the app. Ideally, it would allow you to sort in either direction, perhaps toggling every time you re-sorted the list or maybe doing the opposite when the Option key key pressed.

As an aside, you mention that you're selecting the sort option from the contextual menu. Do you mean you're Control-clicking or right-clicking the selection and choosing the option from the resulting contextual menu?

If so, what version of OmniFocus are you using? The reason I ask, is that in the 1.0.2 sneakypeak version (rev 99863) that I'm running, the sort options no longer exist in the contextual menu. They only seem to be available from the menu bar at Edit -> Sort -> By Data Added. I'm wondering if they were removed on purpose or if this is a regression.