Connected devices in the home represent a potentially grave new privacy threat due to their unfettered access to the most personal spaces in people’s lives. Prior work has shown that despite concerns about such devices, people often lack sufficient awareness, understanding, or means of taking effective action. To explore the potential for new tools that support such needs directly we developed Aretha, a privacy assistant technology probe that combines a network disaggregator, personal tutor, and firewall, to empower end-users with both the knowledge and mechanisms to control disclosures from their homes. We deployed Aretha in three households over six weeks, with the aim of understanding how this combination of capabilities might enable users to gain awareness of data disclosures by their devices, form educated privacy preferences, and to block unwanted data flows. The probe, with its novel affordances-and its limitations-prompted users to co-adapt, finding new control mechanisms and suggesting new approaches to address the challenge of regaining privacy in the connected home.