Ransomware presents a significant and increasing threat to individuals and organizations by encrypting their systems and not releasing them until a large fee has been extracted. To bolster preparedness against potential attacks, organizations commonly conduct red teaming exercises, which involve simulated attacks to assess existing security measures. This paper proposes a novel approach utilizing reinforcement learning (RL) to simulate ransomware attacks. By training an RL agent in a simulated environment mirroring real-world networks, effective attack strategies can be learned quickly, significantly streamlining traditional, manual penetration testing processes. The attack pathways revealed by the RL agent can provide valuable insights to the defense team, helping them identify network weak points and develop more resilient defensive measures. Experimental results on a 152-host example network confirm the effectiveness of the proposed approach, demonstrating the RL agent's capability to discover and orchestrate attacks on high-value targets while evading honeyfiles (decoy files strategically placed to detect unauthorized access).

Honeyfiles are a particularly useful type of honeypot: fake files deployed to detect and infer information from malicious behaviour. This paper considers the challenge of naming honeyfiles so they are camouflaged when placed amongst real files in a file system. Based on cosine distances in semantic vector spaces, we develop two metrics for filename camouflage: one based on simple averaging and one on clustering with mixture fitting. We evaluate and compare the metrics, showing that both perform well on a publicly available GitHub software repository dataset.

Honeyfiles are security assets designed to attract and detect intruders on compromised systems. Honeyfiles are a type of honeypot that mimic real, sensitive documents, creating the illusion of the presence of valuable data. Interaction with a honeyfile reveals the presence of an intruder, and can provide insights into their goals and intentions. Their practical use, however, is limited by the time, cost and effort associated with manually creating realistic content. The introduction of large language models has made high-quality text generation accessible, but honeyfiles contain a variety of content including charts, tables and images. This content needs to be plausible and realistic, as well as semantically consistent both within honeyfiles and with the real documents they mimic, to successfully deceive an intruder. In this paper, we focus on an important component of the honeyfile content generation problem: document charts. Charts are ubiquitous in corporate documents and are commonly used to communicate quantitative and scientific data. Existing image generation models, such as DALL-E, are rather prone to generating charts with incomprehensible text and unconvincing data. We take a multi-modal approach to this problem by combining two purpose-built generative models: a multitask Transformer and a specialized multi-head autoencoder. The Transformer generates realistic captions and plot text, while the autoencoder generates the underlying tabular data for the plot. To advance the field of automated honeyplot generation, we also release a new document-chart dataset and propose a novel metric Keyword Semantic Matching (KSM). This metric measures the semantic consistency between keywords of a corpus and a smaller bag of words. Extensive experiments demonstrate excellent performance against multiple large language models, including ChatGPT and GPT4.

Deception is rapidly growing as an important tool for cyber defence, complementing existing perimeter security measures to rapidly detect breaches and data theft. One of the factors limiting the use of deception has been the cost of generating realistic artefacts by hand. Recent advances in Machine Learning have, however, created opportunities for scalable, automated generation of realistic deceptions. This vision paper describes the opportunities and challenges involved in developing models to mimic many common elements of the IT stack for deception effects.