This article shares case studies from in-depth research that investigates Latino immigrant families' use of technology, focusing on family technology practices that were interest-driven, cross-setting, and in some cases also collaborative among family members. Three cases illustrate ways that families--all of whom included elementary school-age children--were innovative in their use of technology to learn, as well as how digital resources served to help children and parents explore content across settings. Beyond documenting families' existing practices, the study also examined what happened when each family received a tablet device with curated language- and literacy-related content. We focus on three types of connections that families made: 1) aligning access to rich content at home and school leading to more exploration of academically relevant material; 2) expanding parents' roles as collaborative learners of English as a second language among other topics; and 3) digital production that connects civic, STEM, and language practices. We highlight ways in which families used innovative approaches to get the most out of the devices and content they had access to. We also explore how factors including technology infrastructure, opacity of the app marketplace, and cost can constrain families' opportunities to learn with technology.