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I just started using OmniFocus, and I love it. That said, I've never read a single thing about GTD, but I've used TaskPaper for several months before deciding I needed something with a bit more muscle to manage university assignments/other tasks.

Many people have made excellent points in regards to why multiple contexts can make you more efficient, and I happen to agree with them that it should be a supported feature. But my reasons for wanting it implemented are a bit more pragmatic.

I've come to the conclusion OmniFocus needs multiple contexts, if for no other reason than that iCal syncing is apparently dependent on context to figure out what goes in which calendar.

I've got a calendar for Law School Assignments and a calendar for Law School Events (meetings, etc.). In OF, I've got a Folder for my Law School related projects. I've also got projects and tasks outside that folder that have nothing to do with Law School. I find it very intuitive to set a context for an action (e.g.: "email," "website," etc.). However, I also need to be able to indicate a context for which iCal calendar this action belongs to (possible calendars: Law School, Law School Events, Personal, Medical, etc.). I can't simply tell it to throw all my email-context actions into my Law School calendar, for instance. Duplicating contexts hierarchically is also a terrible idea.

Either the way things are synced to iCal needs to change, and I'm not really sure how it could, because in theory the context-to-calendar idea is very efficient, or at the very least OF needs to support a minimum of two contexts, with the second being used to indicate a calendar. So you might have a task that has the primary context "email" and the secondary context "Legal Writing." The user can then use the iCal pref pane to tell OF that Legal Writing context actions go into a specific specified calendar.