"Send Update Request" feature should be available at the Project and Milestone objects. If they are not, at least the contextual menu should make the option unavailable instead delivering the confusing "The Send Update Request on '<<object name>>' has failed for one of two reasons. Either it is not an active work item or else the user’s “Allow Email” property is turned off." message.
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Send Update Request is available for Milestones and Projects, but there has to be work inside of the Project or Milestone for an email to go out. For example, an empty milestone has no real work associated with it. Same if all the tasks inside of that object have been completed. A Project or Milestone need to contain at least one active task assigned to resources that have emails enabled in order for the request to trigger.
Thanks Josh! That's fair enough. I would then amend my request to allow the "Send Update Request" feature to work for Projects and Milestones whether or not they have active sub-objects. :-) Additionally or maybe instead, it would certainly be less confusing to have the item disable itself if it's not an available function in that context.
Unfortunately, this is a tricky one. If there are no active work items then the email would just be blank and there would be nothing to report on. If we hide the button dynamically, that would mean every single time you select any work item the system would have to analyze all sub items in the hierarchy and associated resources and then calculate whether or not the button should be enabled. It would be extremely performance intensive and likely slow down the UI/UX, especially on large projects. There might be another creative solution, but I'm drawing a blank right now.
Sounds like the simple answer would be to modify the outgoing message for the "Send Update Request" to provide information about the object (Project, Milestone or Task) and a link requesting that the user provide updates. Maybe I'm missing a deeper set of logic at play in the app.