Thumbnail images are discreet, yet central navigational tools in increasingly complex visual information environments. Indeed, without thumbnail images there would be no image search: they are an inherent part of the information architecture of most digital information platforms. Yet, how might we understand the role of the thumbnail as an attention technology in the digital economy? And what kind of aesthetic does it produce? This paper examines the legal negotiations of the thumbnail image and the ensuing decision to conceptualize the thumbnail as a functional image against the cultural history of visual attention technologies and the aesthetics of their connective function. Such an endeavour, we propose, allows us to understand and appreciate the significant digital economy and particular aesthetic of the thumbnail image despite its apparent subtlety.