Healthcare decision-makers are constantly challenged by growing healthcare needs in tandem with rising healthcare costs. Disinvesting in technologies and practices that are "low in value" is one strategy to re-allocate limited resources to the most effective, safe and cost-effective technologies. We put forward a health technology reassessment framework and examined the opportunities and challenges on technology disinvestment in Singapore and deliberated on possible solutions. We coordinated and supported a disinvestment programme in 2 hospitals, 1 specialist centre and 9 primary care institutions in the public healthcare sector. The key processes were identifying, prioritising and assessing low-value health technologies and practices, disseminating and implementing disinvestment recommendations, and post-implementation evaluation. Through case studies, we explored the barriers and enablers to the success of the programme. One of the barriers to disinvestment included difficulty in demonstrating a lack of benefit of in-use technologies from published studies. Differing viewpoint and priority might preclude a healthcare leader's support in such initiatives and that posed an unsurmountable hurdle. On the other hand, engaging the stakeholder throughout the evidence review process and striking a balance between rigour and timeliness of review were likely to assure success. Lastly, monitoring the impact on resources and patient outcomes can be diverse and methods need to be developed. Understanding barriers and enablers in health technology disinvestment can translate into improved opportunities for eliminating and minimising resource wastage.