You can set this RegKey via group policy ( Specify wait time to evaluate sensitive content), script or other mechanism for configuring registry keys. *Software\Policies\Microsoft\office\16.0\Outlook\options\Mail* This registry key defines the amount of time to wait to evaluate sensitive content. You need configure the dlpwaitonsendtimeout Regkey (Value in dword) on all the devices you want to implement oversharing popups. When these conditions are met, the policy tip displays untrusted recipients while the user is writing the mail in Outlook, before it's sent.
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