This is an EU-funded project related to cross boarder collaboration for educational purposes supported by information and communication technologies between Danish, Norwegian and Swedish schools. The project started in 2011 and extends to 2014 so this empirically dominated paper reports on early findings related to cross-border collaboration challenges. The aim of the project is to develop innovative cross-border teaching models by the means of user-driven, practice-based co-design processes between practitioners and researchers. In the first year, 18 classes from 13 schools in Denmark, Norway and Sweden in the Öresund-Kattegatt-Skagerack region participated. Organized in so called Nordic class-match groups (consisting of students and teachers from one class in each country) new cross-border teaching models are co-created, tested and evaluated in an iterative process. Since teaching models are subject dependent, the project develop teaching models in several subject domains, i.e. math, language, science and social studies / history. Heretofore findings show, however, that organizational and technical issues have superseded and squeezed out subject-oriented discussions due to surprisingly many practical issues that needed to be handled first. We have identified three major thresholds to overcome. The first is related to technical difficulties in schools when diverse IT systems are to be synchronized. The second threshold concerns scheduling coordination difficulties in order to allow synchronous cross boarder collaboration. The third threshold concerns linguistic and communication difficulties rooted in participants communicating in their respective Nordic language. Being able to communicate within Nordic languages are explicit learning goals in all three schools systems, and therefore part of the project aim and consequently all participants are expected to use their native languages when communicating. The next phase of the project is therefore to find solutions to these technical, organizational and linguistic barriers, and already now we see some barrier breaking models taking shape in the active network of Nordic teachers, students, school leaders, IT support teams and researchers.