Teacher agency in relation to assisting students with their aspirations is not well documented in research literature. This chapter will explore this aspect of student aspirations and draw attention to the work of teachers in this area. The conceptual framing for this chapter draws from a sociocultural understanding of agency, with an emphasis on the school ecology upon which the teachers were working. Data were collected in the form of 14 interviews in a Foundation to Year 12 school context in regional Victoria, Australia. In this case, teacher perceptions of the school culture both facilitated and hindered their ability to assist students with future pathways. Analysis shows how teachers were balancing competing interests of the students, families and the school to assist students with their future goals. Discussions that teachers may have held with previous students about their aspirations in informal ways had now changed due to complications of factors identified, intensifying the pressure on teachers in their ability to make agentic moves.