Trained security experts can be a mitigating factor to sophisticated cyberattacks that aim to violate the confidentiality, integrity, and availability of information. Reproducible sessions in a safe training environment is an effective way of increasing the excellence of security experts. One approach to achieving this is by using cyber ranges, which essentially is a set of hardware nodes that can virtually represent a large organization or system. The Swedish Defense Research Agency (FOI) develops and maintains a fully functioning cyber range and has the ability to automatically deploy sophisticated attacks against organizations and systems represented in this cyber range through a system called SVED.

In this thesis, the capability to deploy different types of cyberattacks through SVED against virtual organizations in a cyber range, CRATE, is investigated. This is done by building a dataset of publicly disclosed security incidents from a database and attempting to represent each of them in SVED, and subsequently instantiating these attack representations against organizations in CRATE.

The results show that the prevalence of at least one CVE-entry (Common Vulnerabilities and Exposures) in the incident description is a key factor to be able to represent an attack in SVED. When such an entry does exist, SVED is likely able to implement a representation of the attack. However, for certain type of attacks a CVE-entry is not enough to determine how an attack was carried out, which is why some attacks are harder to implement in SVED. This was the case for Denial of Service (DoS) attacks, which are too reliant on infrastructure rather than one or more vulnerabilities, and SQL injections, which are more reliant on the implementation of database access.

Finally, CRATE is able to handle almost all attacks implemented in SVED, given that the correct vulnerable application software is installed on at least one machine in one of the organizations in CRATE.