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Designers of interactive technologies have long prioritized user engagement, and today's popular end-user products are irresistibly engaging. Modern technology offers enormous value and convenience, but it has also led to widespread feelings of dissatisfaction, and users report wishing they had a different relationship with the technologies they use. Though families are avid technology users, this eager adoption has come with concerns about the impact of technology on family life and child development, and limit-setting is a salient topic in family contexts. This conversation is complicated by social narratives that pressure families to limit exposure to technology. My dissertation examines how families choose to integrate technology into daily life, how they wish they integrated technology into daily life, and what designers can do to help close the gap between the two. By building tools that families find easy to dynamically use and not use, as it suits their shifting needs, designers can support them in both making technology a meaningful part of daily life and also keeping it within bounds they feel good about. Here, I report first on a series of formative studies to understand families' practices and values related to using technology. Across three investigations, I report on observational, interview, diary, and survey data from both parents and children. These studies show, for example, that many parents feel guilty when using personal devices in front of their children (even when they use them for only brief periods of time), children have a harder time complying with rules that ban technology in certain contexts (e.g., no phones at the dinner table) than rules that ban certain types of technology altogether (e.g., no social networking), and young children find it easier to transition away from screen media when the technology itself encourages them to do so than when parents encourage them to do so without the support of technology. Based on this background work, I next examine how designers might create systems that promote intentional usage behaviors. I present the design, development, and evaluation of two such systems: "MyTime," created for adults, and "Plan & Play," created for children. MyTime is a system-level persuasive technology for intentional smartphone use, and my deployment results indicate that it is effective in changing users' habits in the short-term. Plan & Play translates evidence-based techniques for teaching self-regulation to preschoolers into a digital setting, and a lab study with parent-child pairs suggests that it supports children in engaging with tablets with intention. Across these studies, I examine how motivation, autonomy, family dynamics, and situated activities shape the ways in which families engage with and push back against technology. I argue that today's parental controls, the primary design mechanism for limit-setting in family contexts, undermine children's likelihood of self-regulating their own technology use and do not attempt to support families in mentoring children in becoming thoughtful consumers of technology. In a world where technology is available at every moment, managing one's own media consumption has become an essential life skill. I hope that this work will shed new light on how designers can support users in engaging with technology with intention and leave them feeling more satisfied with their own behaviors. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]