When Outlook is used with an Exchange (or Microsoft 365) account, sent emails are stored in the Sent Items folder in a special Microsoft-specific format: a MAPI object. Unlike received emails, these messages do not have a full MIME format and do not contain internet headers.
This means that:
Information such as the sender, recipient, or message ID is not included as headers in the message.
This information exists, but in the form of internal properties (MAPI), which are not accessible via a simple drag-and-drop.
Thus, when an email is dragged from Outlook to another application (like timeSensor LEGAL), Outlook does not transfer all metadata, because the raw message does not contain internet headers. In other words, timeSensor LEGAL cannot analyze the headers, because they are missing, and automatic classification fails or produces unexpected results.