We would say yes.

We are using the iBoss connector for the first time this school year for our 1-to-1. It was a little rough in the beginning. I, myself, was troubleshooting for about 2-3 months on different issues. Now we believe it is in a good spot and working correctly. We did run into some issues where we believe information was conflicting with itself on the support site and reached out to support to let them know. You should definitely reach out to a support rep and schedule time with them to go over everything. And we do mean everything. If you have the slightest hesitation on something, ask them. And always make sure to have a test device to work with and a second test configuration that mirrors your deployment.

Thank you, I think we're going to hold off on a real deployment until it's been improved. It's currently just too brittle.

We are going through an iboss deployment to K-8 ipads now and running into many of the same issues. Can I ask what you found to alleviate the proxy password issue? We are also running into the issue of when trying to use Self Service it says unable to connect to the server and I can't get around it.

Bypassing the websites the apps connected to usually fixed the proxy authentication issue. We added them to the allow list, we used the ssl bypass, and also bypassed it in the pac file. If you bypass it in the pac file, it will not be filtered and or logged for everyone. We also added the jamf server url to the bypass lists to make sure it was always accessible.

Using this for a few months on ipads and macbooks. It seems mostly fine. We are not seeing slowness. PAC and SSL bypasses seem important for things to work. I get the authentication prompt if I deploy the configuration profile without the connector app. Consequently, if I hide the iboss connector app after it is installed, the ipad works temporarily as intended before the prompt shows up as if there was no app. So I guess the hide method disables the app's functionality and doesn't only remove the icon from the home screen. I ended up pushing the app automatically to everyone and pushing the config profile selectively after that.
Settings > VPN is locked in, but General > VPN > iBoss cloud connector 2020 i > Connect On Demand is not and it seems to allow disabling the former as well... So it was never locked in and 'connect on demand' just flips that switch on. Haven't found out how to prevent that one yet despite ticking the boxes in jamf.

edit: must've been some sort of propagation issue. The Connect On Demand switch now appears locked in my configuration. It didn't happen until the device wiped, though.

So we're looking at the jamf parent app now, and there is an app lock feature. If we app lock to safari, it goes into single app mode and works as expected. If we restart the device while it is in this state, then it seems like iboss connector fails to initialize a subroutine and the ipad cannot receive the unlock command. The mode never times out. I wipe the ipad from a laptop to try again.
This seems like something that must be set for a PAC bypass, but skipping the sub+domains of jamf.com jamfcloud.com jamfpro.com and jamfschool.com did not seem to help so far. Just a heads up for anyone heading that direction.

Hi Emmert,

Did you ever find a fix or work around to remedy your iboss cloud connector 2020 app for iboss filtering issues?  We are having the same issues.

Thank you