Technical, vocational education, and training has remained an explosive topic because it can create a divided society in terms of education and the benefits associated with it. Internationally, it has always been a complex and controversial topic compared to the general education strand. It has presented inconsistent arguments over the years, particularly in Sub-Saharan Africa were policies have too often prescribed it as the panacea to addressing youth unemployment. On the one hand, it seems logical means of addressing youth unemployment and on the other hand, vocationalization has never proven to be a straightforward solution or remedy to youth unemployment in Sub-Saharan Africa. It has not been able to address the mismatch between education and the labour market and equally it has failed to prepare the youth adequately for the specific occupations associated with it. Over the years, reality for individuals has been that general education has the promise of better career mobility and higher wages than vocational streams. Technical, vocational education, and training thus acquired the tag of being 'useless' education and only useful for those with less aspiration for better paying jobs. Yet to date such strong arguments against full acceptance of vocational education and training have not deterred African countries from continuing vocational education and training programmes in public education systems and there is a growing view that it is what is needed, and yet expansion and investment is never directed at the technical, vocational education, and training. Consequently, technical, vocational education, and training continues to maintain its inherently powerful but also paradoxical appeal in Sub-Saharan African education systems. This paper, using the cases of Kenya, Ghana, and Botswana will examine how policies have shifted over time, what has worked for technical, vocational education, and training and what has not worked and why. The paper is cast around the present theme on youth bulge in Sub-Saharan Africa and the potential demographic dividend associated with the bulge.