For whatever reason, MS has made it so Outlook 2016 or newer can't import Entourage data. Then from that conversion into the new version, which I presume you already have. As first mentioned, the easiest way by far is to get Entourage data into Outlook 365 or 2019 is to first import it into Outlook 2011. I'm going to assume you have the Mac version of Entourage.
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