The main aim of this study was to measure the effectiveness of a brief generalisation intervention on teaching adolescents with disabilities to generalise specific social skills to two familiar environments. Participant and parent perceptions on friendship quality were examined. In addition, this study examined the attitudes and behavioural intentions of peers toward individuals with disabilities. Three participants participated in the intervention over a four-week period. Training session took place at the participant’s home and at a local social club and generalisation settings took place at the participant’s after-school activity and/or school. A single case multiple baseline design was employed for each participant across settings. One individual and group session was conducted each week over a four-week period and participants were trained in initiating interactions and conversational skills. Direct observations were conducting over a six week period in the participant’s generalisation settings. All three participants showed gains in social interactions in at least one generalisation setting. Observations showed all three participants generalised atleast one skill to generalisation settings. Participants and parents showed similarities and differences in their perceptions of friendship qulity. Peers showed positive attitudes and behavioural intentions towards individuals with disabilities. It can be concluded that adolescents with disabilities can generalise social skills to other familiar environments, however time and opportunities can influence social interactions, friendships and attitudes.