The Decentralised Web (DW) has recently seen a renewed momentum, with a number of DW platforms like Mastodon, PeerTube, and Hubzilla gaining increasing traction. These offer alternatives totraditional social networks like Twitter, YouTube, and Facebook, by nabling the operation of web infrastructure and services without centralised ownership or control. Although their services differ greatly, modern DW platforms mostly rely on two key innovations: first, their open source software allows anybody to setup indepen-dent servers (“instances”) that people can sign-up to and use withina local community; and second, they build on top of federationprotocols so that instances can mesh together, in a peer-to-peer fashion, to offer a globally integrated platform. In this paper, we present a measurement-driven exploration ofthese two innovations, using a popular DW microblogging platform (Mastodon) as a case study. We focus on identifying key challenges that might disrupt continuing efforts to decentralise the web, and empirically highlight a number of properties that are creating natural pressures towards re-centralisation. Finally, our measurements shed light on the behaviour of both administrators (i.e., people setting up instances) and regular users who sign-up to the platforms, also discussing a few techniques that may address some of the issues observed