Abstract. The CIAO (Chandra Interactive Analysis of Observations) software suite is approaching two decades of service**1 and CIAO remains the primary analysis package from the Chandra X-Ray Observatory. Despite the package's maturity, CIAO continues to undergo active development from a diverse group of developers using a multiple programming languages and build architectures. Keeping up with the ever evolving capabilities in hardware, software, version control systems and paradigm shifts in software development methodologies presents a challenge to both developers and configuration management teams. This paper provides an overview of how the CIAO software suite has evolved over the years with a particular emphasis on configuration management of the system. This paper examines CIAO's integration with various off the shelf software as well as CIAO's packaging and distribution system and how these have evolved. We will conclude with an outlook on the future direction of CIAO infrastructure including possible integration with modern package management systems such as Conda, plans for continuous integration, and use of tools such as pip for extending capabilities in CIAO. **1 CIAO version 1.0 was released October 1999
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