Is there a way to stay within a Task and communicate privately with an individual collaborator? Or blind a message within a Task to only certain collaborator’s?
You can’t have multiple discussions within a task but you can create a dedicated task, for example using “Create follow-up task” button and have the discussion there 
You could also have a subtask in the task to hold another discussion, but it could not be private to the main task collaborators.
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@Ryan_Kowal, You can have the private access you’re looking by making the task in question a child of a new parent task accessible only to those you give access to. Those with access to the child task won’t be able to access the parent task; it will appear as “Private task” to them. This might work well in some use cases.
Larry
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