This paper is an attempt to explore educational issues in a school operating in a prison in the hope that findings will be useful in further and larger-scale research. The objective of the study was to investigate the attitudes of inmates attending the Second Chance School, Domokos prison, Greece, towards the use of computers with the help of the research scale, Computer Anxiety Rating Scale (CARS) by Heinssen, Glass & Knight (1987). The research took place in February 2014. Thirty eight inmate students, from different countries, aged 21 to 45 who were enrolled in the 1st and 2nd year of the Second Chance School were the subjects of the study. The research showed that respondents were very enthusiastic about learning about computers but most were anxious that large amounts of data could accidentally be erased. The learners believed that computers are essential in education and the workplace and also believed that they were able to acquire relevant skills. The final result of the research revealed increased anxiety about computers probably because inmate students have limited access to them. This could be an obstacle in the learning process as a reluctance to use computers could hinder computer assisted learning.