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The DLP Add-On for Outlook on Macs is causing the “Send Later” option to disappear.
Article ID: 224838
Data Loss Prevention Enterprise Suite
While using DLP with Outlook on Mac OS the send later options is disabled
Microsoft has disabled this option in Outlook when an add-on that uses the onSend feature is installed. DLP uses onSend features.
Release : 15.8
Microsoft Outlook 15.x
At this time this is working by design. See the limitations shown here.