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Handheld computers will become an increasingly compelling choice of technology for K-12 classrooms because they will enable a transition from occasional, supplemental use to frequent, integral use. Early evaluations suggest teachers and students respond to handhelds favorably. At the same time, these devices will become communication enabled, through wireless technologies such as infrared beaming or radio-based local area networks. This current research base, however, is insufficient to unlock the value of wireless Internet learning devices (WILDs). An important issue, hinted at but not fully explored in prior work, now must become our central focus of attention. The issue is the nature of the coupling between social and informatic worlds, and within the social and informatic worlds. We articulate three coupling issues: (1) curricular activity spaces versus personal learning connections; (2) integrated vs. synchronized educational databases; and (3) broad vs. narrow technological mediation of discourse.