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I tried you example and got some interesting results.

When I only have a Start Date & Time assigned 1/8/08 9:00AM. I get exactly what you said in your post. When set to Repeat from Assigned, the next Action would get set to Start on 1/8/08 9:01AM. When Assigned from Completion, the next Start Time would be 1/8/08 7:35PM (it's 7:34PM now for me). Okay, all good.

Now, let's set a Due Date and Time. Things get more interesting...
Let's set the Due Date and Time for 1/8/08 11:59PM (eat it _today_ right?).
Now the next Start Date/Time is 1/8/08 9:01AM and Due Date/Time is 1/9/08 12:00AM. Interesting - notice OF used the actual amount of time between the Start Date/Time and the Due Date/Time into the next assignments.

This is really weird, if I Assign from Completion, the next Start Date/Time is 1/8/08 4:40AM (what?) and the next Due Date/Time is 1/8/08 7:39PM (current time is 7:38PM). I'm clearly not telling the tool what I think I'm telling it.

Good Lord have I dug myself into a hole trying to get an Orange badge during the day and a Red badge tomorrow if the item isn't completed. (laughs!). I think my best bet is to not enter a time, then I get my default of 12:00AM and, for these Actions, Repeat from Assigned and Repeat from Completion are pretty much the same.

Pretty weird that the repetition uses the absolute time between Start Date and Due Date to make the next assignment times. I didn't expect that.

To continue your earlier analogy... I don't think I could ever get this confused using Text Edit - it's only when I got to Word that I start F**cking things up! ;-)

Thanks for the company while I figure out how to use this tool in public!