There is a way via installing an additional Microsoft plugin to undelete hard deleted mail (ie. Shift + Del) from Outlook.

It can be found in the Microsoft KB246153 article.  It is fairly straight forward, even a little too much as after installing it I couldn’t tell if it installed correctly.  After you run it, start or restart outlook and then to start using it, all you need to do is right click on the folder and run the “Deleted Items Recovery” either from right clicking or going to Tools > Deleted Items Recovery.
Should you need to be trying to recover mails that were hard deleted you might heave a chance to get them back here before the server wipes them permanently.  It also save the hassle if having to go to archive or backup to try and retrieve the missing file.