I just semi-randomly found this disseration by John W. Maxwell, Tracing the Dynabook: A Study of Technocultural Transformations, which has a good chapter about Squeak. Abstract:
The origins of the personal computer are found in an educational vision. Desktop computing and multimedia were not first conceived as tools for office workers or media professionals— they were prototyped as “personal dynamic media” for children. Alan Kay, then at Xerox’ Palo Alto Research Center, saw in the emerging digital world the possibility of a communications revolution and argued that this revolution should be in the hands of children. Focusing on the development of the “Dynabook,” Kay’s research group established a wide-ranging conception of personal and educational computing, based on the ideal of a new systems literacy, of which computing is an integral part.
Kay’s research led to two dominant computing paradigms: the graphical user interface for personal computers, and object-oriented programming. By contrast, Kay’s educational vision has been largely forgotten, overwhelmed by the sheer volume of discourse on e-learning and the Web. However, an historical analysis of Kay’s educational project and its many contributions reveals a conception of educational computing that is in many ways more compelling than anything we have today, as it is based on a solid foundation of educational theory, one that substantially anticipates and addresses some of the biggest civil/political issues of our time, those of the openness and ownership of cultural expression. The Dynabook is a candidate for what 21st-century literacy might look like in a liberal, individualist, decentralized, and democratic key.
This dissertation is a historical treatment of the Dynabook vision and its implementations in changing contexts over 35 years. It is an attempt to trace the development of a technocultural artifact: the Dynabook, itself partly an idealized vision and partly a series of actual technologies. It is thus a work of cultural history. But it is more than simply a looking back; the effective-history of the Dynabook, its various incarnations, and its continuing re-emergence and re-articulation mean that the relevance of this story is an ongoing question which needs to be recognized and addressed by educators, technologists, and learners today. This dissertation represents an introduction to this case.