There appears to be an NTLM bug in OSX in how authentication is handled with our corporate proxy. On several Macs (and iDevices) Safari, iTunes, Software Updates, AppStore etc all crash when they attempt to authenticate. Unable to find a 'real' solution to this problem and without IT support (all windows/linux environment), my team has come up with a workaround that nearly works out perfectly ... we're using Squid and SquidMan to sit between the web requests and the proxy server. Squid handles the authentication rather than the OS and all is peachy except for 1 thing. I haven't been able to find a way to handle both http and https traffic with Squid at the same time. It appears that squid only handles a single parent proxy server/port.
Our hacky workaround so far has been to install 2 instances of squid on two different servers, 1 to handle http and the other to handle SSL traffic.
We would really like to have at most 1 instance of squid if possible - or better yet a more elegant workaround altogether but I would be very happy with the former. Thank you in advance.
Disclaimer - we are not networking gurus by any stretch and have no control of the proxy server or policies. OSX is not 'officially supported' in our organization but like many shops now find ourselves working on the iOS platform in an environment not conducive to this platform.