Hello, i have the same question. Does this work? Can someone confirm if this is possible or not? Thanks

On a brand new supervised device with default apps, I am seeing that creating two simple web-content filters (plugins) profiles using Apple Configurator 2 and trying to install both of them, only one can be installed successfully at a time. If you try to install a second one via Apple Configurator, you get an error that the profile could not be installed. You can install each one in any sequence you want successfully - but when you try to install a second one while first one is installed, it does not work. Note, I have not even installed any content filter apps yet- just trying to install 2 content-filter plugin profiles at same time. Is this expected behavior?