The current focus on the quality of initial teacher education and effective preparation for the teaching profession requires an in-depth understanding of the challenges during professional experience placements. This qualitative study examined the perceptions of 179 pre-service teachers’ challenges prior to and during their professional experience placements. The online survey data were thematically analysed. The findings highlight challenges during two phases of placement: lived experiences prior to and during placements. An adaptation of Bronfenbrenner’s bioecological systems theory framed the participants’ perceptions of schools’ preparedness to engage with teachers before and during their placements. The theoretical framing of the investigation emphasises a context-conscious understanding of challenges such as open communication, well-structured guidelines, support, and management of multifaceted instructions from higher education providers. The key concerns identified were confidence, planning, behaviour management, time management, differentiation, and professional relationships. The paper concludes with suggestions to support pre-service teachers during placements.