This paper aims to analyze the forms taken by digitally enabled ground campaigns for political elections in the last fifteen years in Anglo-Saxon countries. First of all I will develop a theoretical framework allowing a deeper understanding and the categorization of the different cases of digitally enabled ground campaigns. The first step is the revision of the categories of collective and connective action proposed by Bennet and Segerberg (2013), in order to develop the concept of connective campaigning. I will then turn to integrating Flanagin, Bimber and Stohl’s (2006, 2012) concepts of interactivity and engagement within Stromer-Galley’s (2014) controlled interactivity framework, to provide a new theoretical framework useful to compare different forms of digital management of interactions within connective campaigns. The article also develops the concepts of digital and human infrastructure, in order to distinguish the different components of connective ground campaigns. Once the theoretical frame is completed, the article analyses four case studies of connective campaigns: Howard Dean’s primary campaign; Obama’s presidential campaign in 2008; Bernie Sanders’ campaign for the Democratic Party primary in 2016; and finally Labour Party’s campaign for the general election of 2019, with a specific focus on the app My Campaign Map developed by Momentum. The comparative analysis shows that all these campaigns combine high personalizability in the level of individual involvement with a medium level of interactivity and tightly controlled engagement. This confirms the results of previous research by Stromer-Galley (2014), according to whom the constraints of electoral competition lead organizers to manipulate the affordances of digital technologies in order to reduce the participants’ margins of organizational autonomy; moreover this article adds to Stromer-Galley’s reading a specific focus on the interrelation between digital and human infrastructure as affecting both engagement and interactivity patterns.