When using Caching Sites you should consider any supporting packages you might need to also have so that your primary packages can complete install or updates successfully.
3 common packages to include with your Approved Packages list should be:
chocolatey
chocolatey-compatibility.extension
chocolatey-core.extension
If you find that packages are failing to install or update then these may be a cause. Add them to your approved packages list and update the site cache for each location.
Afterwards select the chocolatey-core.extension package’s menu from Approved Packages list and click to install to all agents. You can also push chocolatey-compatibility.extension or allow auto installer to pick it up and install it during install cycle.
You will need chocolatey-core.extension for many of the packages you want to install or maintain from Chocolatey.org so don’t forget to add these to you Approved Packages list.