Transparent proxies break horribly when you need to deal with HTTPS, and I’m not talking about “oh, you need to install the CA” because that’s necessary for a configured proxy as well.
Chrome in particular breaks on any Google domain because they pin keys as a security measure, when using WPAD or manual system proxy settings it will happily connect.
And before someone says “don’t intercept SSL”, I’ve got Sophos XG deployed on my home network to do content filtering to keep my five year old from accidentally pulling up things she shouldn’t online - she’s not at an age where she gets unsupervised access to the computer, she can’t type (or spell sometimes) properly, etc. but it lets me pull open Leapfrog Academy for her and know if she somehow managed to go to elsewhere by accident the chance of her running into age-inappropriate content is minimal.
Chrome in particular breaks on any Google domain because they pin keys as a security measure, when using WPAD or manual system proxy settings it will happily connect.
And before someone says “don’t intercept SSL”, I’ve got Sophos XG deployed on my home network to do content filtering to keep my five year old from accidentally pulling up things she shouldn’t online - she’s not at an age where she gets unsupervised access to the computer, she can’t type (or spell sometimes) properly, etc. but it lets me pull open Leapfrog Academy for her and know if she somehow managed to go to elsewhere by accident the chance of her running into age-inappropriate content is minimal.