The article examines current challenges in teaching Vulgar and Late Latin (LVLT) at the University of Helsinki, the institution with the longest tradition of teaching LVLT in Finland. Based on structured interviews with researcher-teachers and doctoral students, as well as the author’s own didactic experience, the study identifies institutional, teaching-related, and learning-related challenges for effective LVLT instruction. The key institutional challenges stem from significant reductions in degree requirements and teaching staff, limiting students’ exposure to LVLT. Teaching-related challenges emphasise the need for improved alignment between teaching methods and intended learning outcomes, while learning-related challenges concern declining Latin proficiency and academic skills among graduate students. Despite the difficulties, interdisciplinary and student-centred approaches have proven effective in LVLT teaching. The study highlights the importance of the linguistic, philological, and historical contextualisation of LVLT texts, especially original documents, as well as the necessity of independent study to supplement formal instruction.