Driver controller in outliner not properly working?

I’m trying to create a driver on a model where disabling / enabling a collection filled with clothing parts in the outliner would disable / enable the proper masks on the body mesh to prevent clipping.
Adding the driver works fine, but it simply doesn’t update at all when disabling the “Disable in viewports” button.

It will toggle the mask properly when clicking any of the 3 other buttons on the mask modifier afterwards, so then it does update the driver.
I’m not getting any errors, pretty confused right now.

Is his just straight up not yet supported or just a bug? I’m on v2.82.7