The acquaintance of Museums and Cultural Heritage (CH) institutions with the digital age challenges is of no question a matter of survival. Nevertheless, the dialogue between CH and Information and Communication Technologies (ICT) do not always lead to a harmonious symbiosis. Moreover, the question of if and how ICT could add value to collections, museums and cultural sites and enhance access and communication between stakeholders and users/visitors is a critical open question from many perspectives. In this paper we discuss the main types, obstacles, and benefits of such collaborations, based on interviews held with both CH stakeholders and technology providers, done in the frame of the European project eCultValue.