This is a problem in Outlook when connected to Exchange. Unfortunatley its by design and needs Microsoft to change the system.

However if you change from searching “Current Mailbox” to “All folders” or “All Outlook Items” or “All Mailboxes” then you see all results.

You can change the default option by clicking File -> options -> search

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Outlook only shows recent items in search or only shows 24 items

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