This study examined school counsellors’ and parents’ experiences of a school-based digital mental health service (Smooth Sailing) that screened students’ mental health and provided automated psychological care. The Smooth Sailing service was offered to 4 secondary schools in New South Wales, Australia, for a 6-week trial period with 59 students taking part. The participating school counsellors (n = 4) completed a semi-structured interview to explore their experiences. Parents of students who had consented to being contacted (n = 37/59) were invited to complete an anonymous online survey about their child’s participation. Six parents completed the survey. The school counsellors expressed overall support for the service and cited the ease of service use, its ability to identify students at-risk, and the provision of psychoeducation to students as clear benefits. They identified some barriers to the service, such as parental consent and suggested strategies to improve uptake and engagement, such as incentives, more frequent screening and use with older students. Parents also reported positive experiences with the service, expressing appreciation for mental health screening in schools and a new system to connect them and their child to school counselling services. Taken together, these findings provide initial support for delivering the Smooth Sailing service in secondary schools. Trial registration: This trial was registered with the Australian and New Zealand Clinical Trial Registry (ACTRN12617000977370).