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Based on the current situation (thanks to Rubén), I have drawn the following flow chart.


Gmail and Outlook mailboxes work very differently. While Outlook has folders and allows to add any email to the sent folder, Gmail has views and labels. Users can't add emails to Sent because it is a view that contains all emails where the Mailbox owner's email address can be found in the From field. Workaround: In Outlook create a custom folder (i.e. name ...

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