Schools have an important role in teaching students how to use Social Network Site (SNS) for career purposes. This involves the opportunity for students to practice online career skills. Different types of digital environments are available for schools. There are SNS designed to enable users to interact and network. In addition there are digital environments – like Virtual Learning Environments (VLE’s) – designed to support learning processes but with possibilities to network and interact as well. Little is known about how characteristics of these environments may support the development of online career skills. In this study the suitability of four digital environments – two SNS and two VLE’sto practice online career skills was investigated. The concept of affordances was used to relate the characteristics of the digital environments to how they may stimulate the practice of online career skills. Based on this concept a framework was developed to analyse the characteristics of each environment. In addition, these results were compared with the actual use of the SNS by students. The results show that, although the two SNS appear to offer a stronger environment for practicing online career skills, students do not show more online career behaviour in these environments. Implications are discussed.