Abstract: With the huge transformation in the development of digital screen technology and its consistently decreasing cost, digital billboards are progressively replacing traditional static, two-dimensional poster advertisements in our cities1. Previously, due to the substantial expenditure involved, they were only available to major international brands with vast promotional resources to build their brand fame. Today, however, they are being used increasingly by advertisers to deliver all kinds of messages from simple ones to more sophisticated, interactive storytelling. Soon, however, even newer ways of purchasing advertisements using computers will be introduced by the outdoor media industry to address the public, so potentially everybody will be able to rent out available advertising space and communicate the message. But are we ready for this next step? As there are no proper guidelines or regulations in place for this new medium in the urban realm, today we are facing issues such as no integration of the display’s location into the built environment, no specifications based on knowledge of human perception and the human centric design approach, no control over its content quality, and so called ‘display blindness’2 seems to be a common collective urban experience at night. Taking London as one of the most cutting-edge outdoor digital advertising environments in the world3 (with the largest number of these screens traditionally located in or in close proximity to Piccadilly Circus) this paper discusses various aspects of this new medium. Besides the layout and geometry of the space, it also focuses on navigation and attracting the visual attention of passers-by at night in a practical human oriented context. Additionally, questions regarding complex sensory, social, special and interactional issues and the necessity for interdisciplinary collaboration have been addressed.