The Point-to-Point Tunneling Protocol (PPTP) is used to secure PPP connections over TCP/IP link. In response to [SM98], Microsoft released extensions to the PPTP authentication mechanism (MS-CHAP), called MS-CHAPv2. We present an overview of the changes in the authentication and encryption-key generation portions of MS-CHAPv2, and assess the improvements and remaining weaknesses in Microsoft’s PPTP implementation.