While upgrading the MacOS DLP you may be wondering what's the correct path to upgrade both the DLP Agent and the Web Add-in for Outlook - in particular in what order you should update both. This may be a concern as for the period of the upgrade the environment will be running on a mix of older and newer agents.
This KB focuses on the MacOS Web Add-in for Outlook 1.0.0.0 and 1.0.0.3 as these are the versions of the add-in that are supported by the oldest supported DLP version 16.0 and the latest available DLP version 25.1
DLP 16.0+
Based on that the order in which the add-in or DLP Agent are upgraded is not a concern. Either the add-in can be upgraded first, or the DLP Agent can be upgraded first. In both situations the detection should not be affected.
Note that even though the add-ins and MacOS DLP agents are cross compatible eventually everything should be upgraded and the state where agents and add-ins are not the on latest versions should be a temporary situation during the upgrade process.
More information about deploying and upgrading the add-in:
Deploying the Web Add-in for Outlook on Windows and macOS Endpoints