The purpose of this descriptive survey was to assess and analyse the challenges and suggestions for improving the Out- segment supervision of colleges of education in the Ashanti region of Ghana. The study used 207 link tutors and 334 mentees with a semi-structured questionnaire as primary data collection instrument. Results of the items were analysed using content analysis approach. The study revealed that the Out-segment supervision was being carried out effectively however, there were some challenges that needed to be addressed. Generally, some of the findings were poor vetting of teaching notes, inadequate teaching and learning materials, lack of transportation from college to schools of practice, inadequate advanced preparation by mentees before teaching, poor remuneration, supervisors not arriving on time at mentees’ schools of practice. Management of colleges of education are advised to address these perennial problems until they are no longer teething challenges in the supervision of Out-segment programme.