Adaptive collaboration scripting is the idea that computer-supported collaboration scripts can be adapted during run time in several of their aspects, to provide learning experiences tailored to individual and group characteristics. The pedagogical rationale of this idea is to bring together and reap the benefits of two important learning design approaches, namely adaptation of the learning environment and scripted collaborative learning. In this chapter we analyze some of the major pedagogical and technical issues related to the design and development of systems for adaptive collaboration scripting (ACS systems). At pedagogical level, we provide methodological steps on how to build systems for adaptive collaboration scripting, explaining why it is important to distinguish between “intrinsic” and “extrinsic” aspects of the script. At technical level we present a generalized architecture for systems that adaptively support learners during scripted collaboration sessions. The implementation of this conceptual framework is further illustrated by a case study on the design of a web-based system for supporting the adaptive operation of a “pyramid” type collaboration script.