In the context of changes to the educational settlement (Vickers 2008) and an increasing overlap of education and work, this research project concerns the learning that happens on the part of teachers and students ‘around’ workplace learning initiatives associated with the senior years of second level schooling across the island of Ireland. The field research was undertaken in two schools in the Republic of Ireland and four schools in Northern Ireland during the period between September and November 2013. Further data was generated by way of desktop research of policy documents and extant research, and through the circulation of online surveys with the support of the Institute of Guidance Counsellors in the Republic of Ireland and the Northern Ireland Schools’ Careers Association. The researchers make a number of recommendations around resourcing, timetabling and management; professional development; collaboration; communication and assessment.