Do mail agents start extracting messages beginning from the oldest or the newest message?
The behavior is by design.
Mail Source agent starts extracting messages beginning from the most recent message inside the mailbox. For example, if mailbox size is 200 MB, default PST size is 100 MB, then Mail Source Agent is going to extract the first 100 MB of data beginning from the most recent message. Once this PST arrives to the target and gets processed by the Mail Target Agent - the target mailbox will contain the most recent 100 MB of mail. The next PST file brought from the source is going to contain older messages.
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