As automotive diagnostic systems evolve, proprietary software like Mercedes-Benz Xentry imposes strict hardware and operating system requirements. This paper investigates the viability of running Xentry inside a VMware virtual machine (VM) while maintaining direct communication with a vehicle’s Controller Area Network (CAN) via a J2534 PassThru device. We analyze the latency, driver compatibility, and stability of USB passthrough for devices such as the Tactrix OpenPort 2.0, Mongoose JLR, and Bosch Mastertech. The findings indicate that with specific configuration parameters (USB arbitration, kernel DMA protection, and CPU affinity), a VMware-hosted Xentry environment achieves diagnostic reliability comparable to a bare-metal installation.