Install Umbrella Root Certificate On MAC OS Install the Cisco Umbrella Root Certificate in All Browsers on Mac OS X In Umbrella, navigate to Deployments > Configuration > Root Certificate and click Download Certificate. Double-click the file or drag and drop it on top of the Keychain Access icon in the Applications | Utilities folder. The Add Certificate window appears. Click Always Trust. Double-click the Cisco Umbrella root certificate to open its properties window. Change the When using this certificate pulldown to Always Trust.