Hi all, some one here must have had this issues before!
I have a school that is having issues with Apple Mac gear connecting to PFsense box running proxy.
PFsense needs a log in (each student has a log in).
The Mac's and having massive issues with the PFsense box and you can log in after that you will get a long lag time (compared to windows pc's) and may be a error.
Any thing would be of a lot of help.