Following two successful events in May 2018 and November 2019, the Cultural Informatics workshop was held again in June 2019. Aiming at bringing together projects working on the field as well as researchers and research groups, the workshop provides an opportunity to discuss issues beyond a strict, academic fashion. There are numerous issues that affect all of us working in Cultural Informatics that often remain unsaid or discussed within a controlled environment of collaborators. However, silos needs to brake since the field seems mature enough to proceed with admitting challenges, common problems and even failures. The academic opportunities we often have to come together and discuss, usually allow us to present our breakthroughs and our (significant) research results. However, we all know that our work is a lot more than that. What happens to our work after the end of projects? How do we deal with unwilling organizations and organizational resistance to change? How can we find participants for our necessary studies? How do we build new collaborations and involve a wider public? Issues like these are a big part of our work, nevertheless are rarely discussed in the open. In addition, there is often a feeling that many of us work on very similar topics and we time and gain “re-invent the wheel”. Not only do we need to exchange know-how and tools to save us all effort, but we also need to evaluate and re-set the main goals of our domain. In this manner, we allow the field to evolve in an effective manner and we save valuable resources for meaningful research. This is the gap we wished to fill with the regular organization of Cultural Infomatics workshops.