This is a first-hand account of a head teacher's quest to bridge the digital divide in a school catchment of considerable disadvantage in the late 1990s and early 2000s. It describes the Microsoft Anytime Anywhere Learning project (AAL), which the school helped to pioneer in the UK. From this, the paper aims to provide some fresh perspectives on the deficit of IT provision which has inhibited home learning during the COVID-19 pandemic 'lockdown'. Through referencing the AAL project, the author also calls into question the notion that bridging the digital divide is the great educational panacea, a view which has become the received wisdom among certain politicians and educationalists.