After over 6 highly successful years on orbit, the Chandra X-ray Observatory continues to deliver world class science to members of the X-ray community. Much of this success can be attributed to an excellent space vehicle, however; the creation of several unique software tools has allowed for extremely efficient and smooth running operations. The Chandra Flight Operations Team, staffed by members of Northrop Grumman Space Technology, has created a suite of software tools designed to help optimize on-console operations, mission planning and scheduling, and spacecraft engineering and trending. Many of these tools leverage COTS products and Web based technologies. We describe the original mission concepts, need for supplemental software tools, development and implementation, use of these tools in the current operations scenario, and efficiency improvements due to their use.