The project focuses on evaluation of web-based systems for on-line tutoring of project courses within two international engineering master’s program, Robotics and Simulation of manufacturing processes. Sharing and communication of advanced information stresses the demand for evaluation of new web-based technologies that can be used in different organizational contexts cross-country. Both programs consist of work-integrated learning projects with industry, international students and academy collaborating on distance. Cohesive for these projects are that they deal with visualization of complex technical information on post-graduate level. The challenge is to support on-line interaction, sharing of applications and information and on the same time solve actual industrial problems in collaboration with industry partners and professional institutions. How can web-based communication tools for application sharing, support problem solving and learning within work-integrated-learning environments? There has been extensive research done on online tutoring in higher education (De Smeet et. al., 2008; Hawkridge and Wheeler, 2009), but there is still a lack of high qualitative online-tools for sharing of complex technical information. In this research we evaluate standard systems for screen sharing, integrated voice and video, information and application sharing such as WebEx, Adobe Connect, Remote Assistance, SharePoint and Skype among many more systems. An overall evaluation of more than 40 systems shows that only a few can accomplish advanced application sharing. Through interviews and participatory observations in real-time settings of teachers on campus tutoring students at companies sharing and discussing advanced constructing 3D-models for manufacturing, show that we have to re-consider standard web-based tools. Problems like connection disturbance, not coming through firewalls, lack of good sound and pedagogical issues during the sessions stresses the need for further evaluation of reliable technologies. It also raises issues about how to emphasize learning in collaborative engineering contexts. The view of learning is that it is constructed through communication and socialisation and must also be supported online (see for example Säljö, 2000; Wenger, 2000). The continuous evaluation will result in a representation of requirements for didactical and generic scenarios and high technology web-conferencing systems adjusted for industrial engineering project courses when collaborating and solving advanced problems.