Continuous professional development for workers is a sure way of keeping staff with up-to-date knowledge, skills and values for effective and efficient delivery on their jobs. The case of colleges of education, the trainers of teachers, cannot be underrated. Every major decision taken by the tutor on what to teach and how to teach it, when to teach could be positively impacted if the tutor is updated on trends of events at the sector. Even though the realization of importance of CPD is getting its root among stakeholders, a number of factors militate against successful hosting of the programmes. This research was therefore conducted in 2017 to unearth the challenges and to help discover their root cause. The study employed case study approach under qualitative design. Data were collected from four principals through semi structured interviews whilst four vice principals and twelve college tutors participated through open-ended questionnaire. Manual coding was adopted under thematic analysis. It was found among other things that training logistics /inadequate funding, limited time, poor attitude due to resistant to change among staff members, inadequate supervision and motivation are the challenges confronting college-based departmentalised programmes. It was concluded that multi factors come to play in challenging the success of any CPD programme organised for the staff of the colleges of education. It recommended that a holistic approach is adopted through involvement of all stakeholders and a comprehensive study initiated into ways of combating the challenges in order to ensure sustainability.