OpenSmalltalk-VM is a virtual machine (VM) for languages in the Smalltalk family (e.g. Squeak, Pharo) which is itself written in a subset of Smalltalk that can easily be translated to C. Development is done in Smalltalk, an activity we call “Simulation”. The production VM is derived by translating the core VM code to C. As a result, two execution models coexist: simulation, where the Smalltalk code is executed on top of a Smalltalk VM, and production, where the same code is compiled to executable code through the C compiler. In this paper, we detail the VM simulation infrastructure and we report our experience developing and debugging the VM within it. We mention some of the limitations and how we worked around them. We discuss specifically how we use the VM simulator to develop and debug two core VM com- ponents, the garbage collector and the just-in-time compiler. Then, we discuss how we use the simulation infrastructure to perform analysis on the runtime, directing some design decisions we have made to tune VM performance.