The Personalized Integrated Educational System (PIES) design theory is a design recommendation regarding the function and features of Learning Managements Systems (LMS) that can support the information-age learner-centered paradigm of education. The purpose of this study was to improve the proposed functions and features of the PIES design theory such that it is compatible with the technological needs of the information-age, learner-centered paradigm of education. Four schools or educational systems that embodied all or some of the characteristics of the learner-centered, information-age paradigm were selected through a purposeful, theoretical sampling process. They were selected based on how useful they would be in extending and improving the design recommendations for PIES and the extent to which the naturalistic cases had transitioned into the learner-centered, information-age paradigm of education. Research participants within these schools were chosen through a non-probability sampling method. Twenty teachers agreed to participate and were interviewed and observed. Data collected in the form of interview transcripts and observation notes were analyzed to reveal functions and features that could be added and removed from the PIES design theory. Data were analyzed to also reveal factors that encouraged/discouraged technology use, implementation, and policy. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]