Migration legacy systems to cloud platforms is a knowledge intensive process. There is an ever increasing body of knowledge reporting empirical scenarios of successful and problematic cloud migration. Reusing this body of knowledge, dispersed and fragmented over the academic/multi-vocal literature, has practical values to mitigate costly risks and pitfalls in further projects of legacy to-cloud and cloud-to-cloud migration. In line with this, knowledge management systems/platforms pertinent to cloud migration are a prime prerequisite and a strategic imperative for an organization. We have conducted a qualitative exploratory study to understand the benefits and challenges of developing Knowledge Management Systems (KMS) for cloud migration in real trials. Whilst our prototype system demonstration supported the importance and bene-fits of developing Cloud Migration KMS (CM-KMS), our semi-structured industry interview study with 11 participants highlighted challenging impediments against developing this class of KMS. As a result, this study proposes nine significant challenges that cause the abandon of the design and maintenance of CM-KMS, including continuous changes and updates, integration of knowledge, knowledge granularity, preservation of context, automation, deconstruction of traditional knowledge, dependency on experts, hybrid knowledge of both vendor-specific and vendor-neutral cloud platforms, and parsimony. Our results inform cloud architects to pay attention to adopt CM-KMS for the legacy-to-cloud migration in their organizations.