In Infrastructure-as-a-Service (IaaS) clouds, the development process of a ready-to-use and reliable infrastructure might be a complex task due to the interconnected and dependent services that are deployed (and operated later on) in a concurrent way on virtual machines. Different timing conditions may change the overall initialisation method, which can lead to abnormal behaviour or failure in the non-deterministic environment. The overall motivation of our research is to improve the reliability of cloud-based infrastructures with minimal user interactions and significantly accelerate the time-consuming debugging process. This paper focuses on the behaviour of cloud-based infrastructures during their deployment phase and introduces the adaption of a replay, and active control enriched debugging technique, called macrostep, in the field of cloud orchestration in order to provide support for developers troubleshooting deployment-related errors. The fundamental macrostep mechanisms, including the generation of collective breakpoint sets as well as the traversal method for such consistent global states, have been combined with the Occopus cloud orchestrator and the Neo4J graph database. The paper describes the novel approach, the design choices as well as the implementation of the experimental debugger tool with a use case for validation purposes by providing some preliminary numerical results.