The study intended to unravel critical IT project showstoppers which tend to halt IT projects temporarily or permanently, and ultimately cause them to fail, by positioning them in the systems development life cycle (SDLC) framework. Interviewing 8 IT project and program managers of the banking and telecommunications industries in Ghana individually and in a group, 19 critical showstoppers were identified spanning the whole SDLC. Generally, it was observed that for the successful completion of IT projects, the expertise and availability of project managers and team members are critical. Again, the project manager must be able to prove that the project is in line with the objectives and strategic direction of the business, is being mounted to gain competitive advantage, and has a solid business case. Thirdly, funding is key at all stages of the cycle, as well as approval for continuation at various stages.