As cyber attacks are an ever-increasing threat to many organizations, the need for controlled environments where cyber security defenses can be tested against real-world attacks is increasing. These environments, called cyber ranges, exist across the world for both military and academic purposes of various scales. As the function of a cyber range involves having a set of computers, virtual or physical, that can be configured to replicate a corporate network or an industrial control system, having an automated method of configuring these can streamline the process of performing different exercises. This thesis aims to provide a proof of concept of how the installation of software with known vulnerabilities can be performed and examines if the software is vulnerable directly after installation. The Cyber Range And Training Environment (CRATE) developed by the Swedish Defence Research Agency (FOI) is used as a testbed for the installations and FOI-provided tools are used for launching automated attacks against the installed software. The results show that installations can be performed without Internet access and with minimal network traffic being generated and that our solution can rewrite existing software packages from the package manager Chocolatey to work with an on-premises repository with an 85% success rate. It is also shown that very few publicly available exploits succeed without any manual configuration of either the exploit or the targeted software. Our work contributes to making it easier to set up environments where cyber security research and training can be conducted by simplifying the process of installing vulnerable applications.