In 1997, the Government of Jamaica signed a three-year cooperative agreement with the Government of Cuba to support Jamaican education through the provision of teachers of Spanish, mathematics and the sciences. After several renewals, the programme is in its 26th year, with 76 Cuban teachers currently resident in Jamaica and serving at the primary, secondary and tertiary levels of the country's education system. Through focus group discussions with 32 teachers in the 23rd cohort, this article reports on the linguistic insertion of the teachers into their Jamaican classroom environments. It assesses the strengths and limitations of the linguistico-cultural preparation of the teachers for working in the Jamaican education system, and documents their sociolinguistic and cultural adjustment experiences. Results indicate that while the information and training sessions on pedagogy were useful and informative, the intergovernmental cooperative agreement programme could benefit significantly from the inclusion of a strong and targeted initiative designed to initiate teachers into Jamaican sociolinguistic realities.