Verify the Updater, "Mac System Updates" is turned on in Rules > Software Rules > Updaters.
Move the Agent into a Policy that has the Control Mode turned off.
Begin the Operating System upgrade.
After the upgrade has completed, move the Agent back into the relevant Policy.
Additional Information
More information on this can be found in the User Guide chapter, "Managing Computers".
The Agent will go through Initialization after being moved back into a Policy that has the Control Mode turned on.
To ensure compatibility with the Agent new Operating Systems will undergo final validation once it is released for General Availability. VMware Carbon Black's support for new Operating Systems varies:
Maintenance Releases (service packs) - Target 30 days
Minor Releases (Red Hat 6.6 to 6.7, Mac OS 10.10.4 to 10.10.5) – Target 30 days
Major Releases (Windows 8.x to Windows 10, Mac OS 10.10 to 10.11) – Target 90 days