Sunsama already keeps track of any alterations to a task, including resetting the due date. I've always wanted a task manager to give me a 'nudge' after I've put a task off a certain number of days so it doesn't fall into the dreaded black hole of good intentions + serial non-action. (Don't you hate that?)

What if Sunsama gave us an (optional) alert during daily/weekly planning. Maybe you'd just make procrastinated tasks a different color or perhaps give us an actual reminder during planning. Something like, "The flagged items have been postponed [x] times. Would you like to break them into smaller tasks or consider moving them to the Backlog?"

You, of all teams, would likely have even better wording, but the idea would be to help us notice when a task has become dead weight we're carrying forward. No one needs the anxiety!