Transparency

Always a good question, set the Proxy up as transparent?

Good

The justification I've generally used for creating a transparent proxy regime, is I don't want to go to each workstation and configure the proxy settings.

  • What happens we have legitimate new users on the network?
  • What happens when someone needs to reinstall their system
  • What happens when Windows 8 login requires Internet Access
    • note that in the 1st RTM of Windows 8, the first login to an 'internet microsoft account' will fail.

Alternative

Unfortunately, transparent proxies have problems with sites using SSL, it breaks my logins.

The better alternative? (No don't remove the proxy)

Web browsers have for a while now supported 'finding' what the proxy configuration is in a network.