The ubiquity of mobile devices, social media and live-streaming platforms have changed the way individuals forge social connections to community. As “networked individuals” these technologies allow us to have community when we want it, on our own terms. This chapter explores two diverging trends in the observance of the Jewish sabbath among non-Orthodox Jews in the United States. The increased practice of live-streaming worship services on the sabbath represents a trend towards engagement with technology to connect to tradition. On the other hand, the increasing popularity of the “digital detox” represents a trend towards technological disengagement as a means of connection. Viewed through the lens of networked individualism, I conclude that both practices facilitate personal choice in negotiating the sabbath as a cornerstone of Jewish practice.