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I'm glad I wasn't the only experienced hand who found that confusing! Why do you want a tickler context in addition to the perspective? I can see a reasonable case for using the tickler projects, if you want to have an easy way to see what is going into the main flow for any given month, for example. I can't see why a tickler context would be desirable, however; could you elaborate on your thoughts there? I'm always interested in seeing different approaches...

A further experiment that you could try, just to eliminate the possibility that the deselection is due to an unintended and unnoticed mouse click during the operation, would be to use the inspector or the contextual pop-up menu to set the context of the action being assigned a new context. If you don't see the funny behavior using those options, then the issue probably doesn't have anything to do with whether the actions are blocked, etc.