Background: Contemporary adolescents use e-mail for a variety of purposes, including peer communication and education. Research into these uses has focused on typically developing individuals; much less is known about the use of e-mail by exceptional youth. Aims: The present study examined the structure and form of e-mail messages sent by adolescents with and without a history of specific language impairment (SLI). Methods & Procedures: Thirty-eight adolescents with a history of SLI and 56 typically developing (TD) peers were assessed on measures of nonverbal abilities, core language skills and literacy skills (reading and spelling). The participants were asked to compose an e-mail reply to a standard e-mail sent by an experimenter. These reply e-mails were coded for linguistic structure, readability and spelling errors. Two adult raters, blind to the participants' language ability, judged how understandable the e-mails were, how grammatically correct the e-mails were, and also the sender's command of the English language. Outcomes & Results: Adolescents with a history of SLI produced e-mails that were similar to those sent by their TD peers in terms of structure and readability. However, they made significantly more spelling errors. Furthermore, the adult raters considered the messages from participants with a history of SLI to be of poorer standard than those sent by their TD peers. Conclusions & Implications: The findings suggest that the e-mail messages of adolescents with a history of SLI provide indicators of the sender's language and literacy skills. Implications for intervention and technology development are discussed. © 2011 Royal College of Speech and Language Therapists.