[needles27]

I should clarify that the extra windows open up not when I select from the OF menu, but rather from the notification in the menu bar, near the clock. I haven't replicated this problem with Due Dates since it occurred sometime in the past with one of the Sneaky Peek versions because I am careful to be only working with one open window. It hasn't happened since. (Although maybe it is and I don't know!)

[abh19]

Ah, I see. I forgot about that menu.

I tested it that way and the due soon item updates normally for me. Maybe it was a problem with an older Sneaky Peek version & you can go back to using multiple windows now.

[bluerings]

Thanks very much for all of your help. Some information to add: first, I've only had one*OF window open when I've had this problem, so I don't believe the number of windows pertains to the problem that I'm having. Second, I ran a similar experiment where I created an action due in 48 hours and 2 minutes (due soon preferences set to 2 days). When the minute struck, there was no change in styling. Waited one more minute and still no change in styling. Switched to "due soon" perspective and back and the styling was there. Ran experiment again (auto styling failed again) and changed "due soon" preferences to 3 days and back to 2 and got the styling again.

So at least the problem is reproducible.

EDIT: Now the auto-styling works automatically and I can't reproduce the problem. I'll keep playing around and look for conditions that consistently produce it.