The dual system of vocational education and training in Germany is characterized by the cooperation between different educational institutions as vocational schools and companies. Information and Communication Technologies (ICT), e.g. digital report portfolios, are used to organize and strengthen the cooperation between those involved in vocational education. The main question in this article is which factors influence the use of digital portfolios in vocational training. By presenting findings from an online survey, factors are examined that may improve the digitalization of collaborative learning between vocational schools and companies by using digital report portfolios – from the perspective of both apprentices and in-company trainers.