CKB:Macro security setting
When starting Outlook you might get an warning dialog like shown below.
In case the macro security setting is activated, Outlook will only load add-ins which are listed in the trusted publisher certificate store.
To prevent the security warning and/or an unloaded add-in, the certificate has to be added to the trusted publisher store. This can be done manually or via GPO. Please make sure the certificate is added to Trusted Publisher as shown in the screenshot.
Download the Cryptshare for Outlook certificate that is applicable to your installer: