I am running into issues where some Macs are not installing a package that is set to deploy upon enrollment completion, yet marking it complete in the policy log. To combat this, I created a Smart Group that checks for the application and if missing, runs an ongoing policy to deploy the package again. Has anyone run into this and found a better way around it? The biggest pitfall with my cobbled-together solution is that apps will more than likely install and then get reinstalled. Perhaps there's a way to trace it to the root cause so that I am sure that required apps are deployed upon enrollment?
I’d be interested in knowing the nature of the package...For example does it install any kernel extensions? Where does the package lay files down to otherwise? With the continuous enhancements to operating system security, some locations which were formerly acceptable may not be any longer. With each new release of macOS, I find myself having to reformulate packages to go to correct spots or in some rare cases I have it go to different spots based on different versions. One big change in Catalina is that the user template is no longer in the same location. That along with Catalina putting the core is in read only mode. For instants I used to have a package that laid down some core internal only documentation to the root of the hard drive and that is no longer a viable option exactly as I did it in Mojave. I have since had to rework that package just a bit.