Adaptive Hypermedia (AH) can be considered the solution to the problems arising from the “one-size-fits-all” approach to information delivery prevalent throughout the WWW today. Adaptive Educational Hypermedia (AEH) aims to deliver educational content appropriate to each learner, adapted to his or her preference and educational background. The development of AEH authoring tools has lagged behind that of delivery systems. Recently, AEH authoring has come to the fore, with the aim of automating the complex task of AEH authoring, not only within a system but also porting material between different AEHs. Advances in intra-system automation are described using the LAOS framework, whereby an author is only required to create a small amount of educational material that then automatically propagates throughout the system. Advances in inter-system conversions are also described; the aim is to move away from a “create once, use once” authoring paradigm currently in force with most AEH systems, towards a “create once, use many” paradigm. The goal is to allow authors to use their content in the AEH delivery system of their choice, irrespective of the original authoring environment. As a step along this road, we describe the usage of a single authoring environment (MOT) to deliver content in three independently-designed Educational Hypermedia systems—AHA!, WHURLE and SCORM-compliant Blackboard. Therefore, this chapter describes advances in automatic authoring and conversion towards a simple and flexible AEH authoring paradigm.