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You have kind of a confusing arrangement. Basically, you have a "tickler" context, which is what you are marking these tickler actions, until you move them into other contexts. You are finding that sometimes when you drag and drop an action from the tickler context to another context, the tickler context becomes deselected, sometimes not. I can't discern any relevant difference between these actions that would cause the context to become deselected. If you hit undo and drag that same action again, does the tickler context become deselected again?