The challenging task of establishing meaningful translanguaging in multilingual classrooms necessitates negotiation between different stakeholders. Such negotiation requires investigation of the contexts and ways in which translanguaging may be implemented as a suitable teaching strategy. The aim of the current study was to elicit practical and pedagogical issues of translanguaging in the classroom via interviews with three different groups of stakeholders: language education researchers, teachers, and multilingual learners. We visited four differently composed multilingual high schools from which concrete examples were recalled in semi-structured interviews on the topic of translanguaging with the selected stakeholders. Adopting an iterative study design, interviewees were presented with daily life examples from the school visits as well as statements from other stakeholder interviews. Their statements and reactions to the statements of others were recorded, qualitatively analysed and categorised. Overall, seven distinct pedagogical challenges concerning a translanguaging pedagogy emerged from the interview analysis: (1) Side effects; (2) Goal formulation; (3) Learning the language of schooling; (4) English and other semiotic resources; (5) Affective functions; (6) Effort; and (7) Confusion. These palpable pedagogic issues may be helpful in understanding how translanguaging in multilingual contexts can be implemented, thus bridging the gap between theory and practice.