In theory, collaboration is a key component of education in Aotearoa New Zealand. In practice, however, cross sector collaborative relationships are not so easily established or maintained, even when collaboration is 'mandated' through government policy. This research explores the perspectives of nine teachers from one Kahui Ako/Community of Learning (Kahui Ako), who discussed the successes and challenges they experienced when collaborating across sectors. With commitment to collaborative work, the research participants were able to cross the borders that exist within and extend beyond the education sectors, exploring exciting new frontiers of leadership and learning. The teachers' experiences were analysed using a social learning theory lens, highlighting the complex nature of cross-sector collaboration. It is hoped this research will support other education communities to evaluate the effectiveness of their own collaborative endeavours.