There are some things we've been doing to make this process smoother. Unfortunately, there's really nothing we can do beyond providing information on how to get the system extension installed and set up in the easiest possible way. The requirements, and changing series of steps with different versions of macOS, are set by Apple.

There is more information available for various deployment methods in the misconfigured agents page in the portal (click the link in the macOS Fleet Readiness widget in the Command Center). If you're deploying manually or via RMM, you can open the Huntress app once it's installed on the endpoint and it will walk you through the process.

Marking this as closed, though we're still continuing to iterate on improvements.

We feel your pain Tyson. If you are able to, an MDM would be the best method for deployment, you could automatically provision the needed apple system settings without having to surface them up to end users. If performing installations via RMM or manually would love to sync up with you to learn more about your environment, tools, and how we can ensure smooth installation and configuration. Please feel free to reach out at russ.bashaw@huntresslabs.com