Hi,
Outlook for Mac builds a local database of recently used addresses from email messages that are stored in the user's identity. This database is named "Recent Addresses" and is located in the following directory, depending on the version of Outlook
for Mac:
Outlook 2016 for Mac:
\Users\<username>\Library\Group Containers\UBF8T346G9.Office\Outlook\Outlook 15 Profiles\<Profiles name>\Data\Recent Addresses
Outlook for Mac 2011:
\Users\<username>\Documents\Microsoft User Data\Office 2011 Identities\<Identity Name>\Data Records\Recent Addresses\
You may consider to move the Recent Addresses database from the Outlook 2011 directory to the corresponding Outlook 2016 directory to see the result.
Regards,
Steve Fan
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