In response to the demands of digital transformation, organizations increasingly rely on IT outsourcing to integrate advanced technologies and optimize operations. This study examines the challenges that IT vendors confront in outsourced IT development projects, with a specific focus on project initiation, execution, and implementation. Using a case study of a Danish IT consultancy firm, the research identifies relational and organizational factors, comprising client digital maturity, communication, relationship management, and contract clarity as essential for project success beyond the typical project constraints of time, resources, and deliverables. The initiation phase emerges as particularly critical, which underscores the need to assess client maturity and align expectations early. Moreover, strong client-vendor relationships foster trust, effective communication, and improved project continuity. The findings suggest a framework that combines both operational and relational factors, emphasizing that a holistic approach helps IT consultancies align more effectively with client expectations, achieve better project outcomes, and build lasting partnerships. This study contributes to the literature on IT outsourcing by highlighting the multifaceted nature of outsourced IT projects and by providing practical insights for IT vendors when navigating the complexities of client engagements.