Outlook now showing all emails on Office365 portal
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Outlook does not display old messages, some strange attempt at trying to make Outlook handle large mailboxes.
You can change the amount of messages shown as follows.
Start Outlook. On the File tab, click Account Settings, and then click Account Settings. On the E-mail tab, double-click your Microsoft Exchange account. In the Change Account dialog box, drag the Mail to keep offline slider to the desired number of months or to All to synchronize all email messages.
More details here: https://support.microsoft.com/en-us/help/2733062/only-a-subset-of-your-exchange-mailbox-items-are-synchronized-in-outlook-2016-or-2013
Hope this helps