The rise of Instant Messaging (IM) across enterprise networks not only has changed the landscape we chat, but also poses serious challenges to network administrators who want to block or monitor the activities. IM came with a large varieties (from AIM to Yahoo Messenger) using different ports to communicate, and is gradually evolving (like the newer version of MSN: Windows Live Messenger, or MSN Shell) into the Skype model that uses not only 80 and others, but also the default secure port 443; It makes the packet sniffing of IM now extremely difficult, if not impossible. This ever-changing IM face of computer communications has forced one back to the origin, i.e., monitoring and control of the whole activities of an individual PC. TupEnterprise is just such an effort that uses the EIM (Employee Internet Management) base of TupSight, coupled with the EIA (Employee Intranet Administration) functions of TupView, with the emphasis on IM monitoring and control. TupEnterprise not only logs and captures the Internet communication data, but also records every meaningful activity of a computer host over a LAN; It can continuously track and play back the screenshots of every PC and generates statistical reports for a given period; It automatically acquires the system information of PC hosts for better management of information technology environment; It virtually backs up all kinds of IM chats such as Skype, Yahoo Messenger, and Google Talk.