Research libraries were among the first to embrace and exploit the potential of the World Wide Web after its debut in the 1990s. They quickly began constructing virtual information landscapes, including policies, services, and collections that not only shaped but also defined the realms of possibility within such terrain. In their roles as both terra-formers and cartographers of these spaces, libraries generally modeled the virtual terrains as electronic counterparts of physical libraries. In recent years, gaps have materialized in the virtual terrain, meaning the landscapes they constructed do not provide certain services, resources, or possibilities expected by emerging user populations like the millennial generation. These rifts often represent fundamental disconnects between the values of today's library users and the historical, core values of libraries that shaped the first generation of online information landscapes. In this article, the authors classify those disconnects into three categories--technology, policy, and unexploited opportunities--and discuss ways academic libraries can create next-generation landscapes to address these gaps. If academic libraries want to retain and expand their usefulness for online users in the next decade of the Web, these core disconnects must be addressed today. (Contains 4 endnotes.)