Lifelong learning and career planning for the marginalized group of imprisoned persons and monitoring during and after serving the sentence (building the bridge:bridging the gap) is of key importance for successful integration of the target group into knowledge society and information society, which includes the possibility to control their career and their life path, a precondition for social independence that is of exceptional importance. Our project will, with the help of a web application, develop a comprehensive alternative mode of teaching – a bilevel tutorial system BRIDGE, which will interconnect activities taking place during imprisonment and will continue their implementation after prisoners' release. The combination of the tutorial system and the use of the web application will allow the individual to design and realize a personal educational and vocational path. The tutorial system will on the first level enable the acquirement of education content (communication skills, social skills, job-finding skills, ICT, learning techniques), and on the second level it will provide the persons during and after serving the sentence of imprisonment a link to competent educational guidance institutions. The web application will enable tutors and convicts to plan and monitor the education path of each individual in prison and outside it. It will also provide an overview of project progress in partner states. Monitoring and assisting individuals after release is of key importance to a successful reintegration into society. The project will strive towards unification, but also bearing in mind the data acquired through the analysis, thus adapting the system to each country's legal and educational system. The alternative aspect of the teaching approach refers to specific features of the target group, for it includes the same group in different social environments (in prison and after serving the sentence).