In the context of Outlook add-ins, the behavior regarding the ItemSend event and offline capabilities is influenced by the Outlook client's settings and the add-in's implementation.
- The Offline toggle is a significant factor in controlling the behavior of the add-in in the Windows client. When the Offline setting is ON, the email can be sent without the add-in's validation, as it does not attempt to reach the add-in. Unfortunately, there is no manifest or code way to override this behavior; it is primarily controlled by user or admin settings.
- Currently, there is no direct way to hook into the send/receive event that occurs when coming back online to run validation code on drafts. Since the add-in would not be in the Compose pane at that time, the Item context would not be available. Therefore, running the same add-in or another piece of code to validate the draft upon reconnecting is not a supported option.
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