In the following paper, the case of Experiments in Automatic Writing, a festival-project that took place in October 2011 at Fournos Centre for Digital Culture in Athens, Greece, and involved collabora-tive writing and performance with the use of digital media, is presented and discussed. The project lasted for 4 days and involved 42 writers, playwrights, journalists, artists, poets, chat users, performers, actors, musicians, a visual artist and a chat bot. The article reflects on the so-cial, theoretical, writing and performative circumstances that gave rise to the project as well as its intentions and outcomes. By analyzing in depth the project, a reflective contribution to the field of digitally enhanced performance and theatre gamification practices is intended, from the point of view of the designer of the event as well as that of the practitioner. Some suggestions are made with regards to possible future uses of the methodology developed within the project framework in the arts and education sectors.