Phishing is one of most common and effective attack vectors in modern cybercrime. Rather than targeting a technical vulnerability in a computer system, phishing attacks target human behavioral or emotional tendencies through manipulative emails, text messages, or phone calls. Through PyAntiPhish, I attempt to create my own version of an anti-phishing solution, through a series of experiments testing different machine learning classifiers and URL features. With an end-goal implementation as a Chromium browser extension utilizing Python-based machine learning classifiers (those available via the scikit-learn library), my project uses a combination of Python, TypeScript, Node.js, as well as AWS Lambda and API Gateway to act as a solution capable of blocking phishing attacks from the web browser.

Studies on underground forums can significantly advance the understanding of cybercrime workflow and underground economies. However, research on underground forums has concentrated on public information with little attention paid to users’ private interactions. Since detailed information will be discussed privately, the failure to investigate private interactions may miss critical intelligence and even misunderstand the entire underground economy. Furthermore, underground forums have evolved into criminal freelance markets where criminals trade illicit products and cybercrime services, allowing unsophisticated people to launch sophisticated cyber attacks. However, current research rarely examines and explores how criminals interact with each other, which makes researchers miss the opportunities to detect new cybercrime patterns proactively. Moreover, in clearnet, criminals are active in exploiting human vulnerabilities to conduct various attacks, and the phishing attack is one of the most prevalent types of cybercrime. Phishing awareness training has been proven to decrease the rate of clicking phishing emails. However, the rate of reporting phishing attacks is unexpectedly low based on recent studies, leaving phishing websites with hours of additional active time before being detected. In this dissertation, I first present an analysis of private interactions in underground forums and introduce machine learning-based approaches to detect hidden connections between users. Secondly, I analyze how criminals collaborate with each other in an emerging scam service in underground forums that exploits the return policies of merchants to get a refund or a replacement without returning the purchased products. Finally, I conduct a comprehensive evaluation of the phishing reporting ecosystem to identify the critical challenges while reporting phishing attacks to enable people to fight against phishers proactively.

Despite extensive research by the security community, cyberattacks such as phishing and Internet of Things (IoT) attacks remain profitable to criminals and continue to cause substantial damage not only to the victim users that they target, but also the organizations they impersonate. In recent years, phishing websites have taken the place of malware websites as the most prevalent web-based threat. Even though technical countermeasures effectively mitigate web-based malware, phishing websites continue to grow in sophistication and successfully slip past modern defenses. Phishing attack and its countermeasure have entered into a new era, where one side has upgraded their weapon, attempting to conquer the other. In addition, the amount and usage of IoT devices increases rapidly because of the development and deployment of 5G network. Although researchers have proposed secure execution environment, attacks targeting those devices can often succeed. Therefore, the security community desperately needs detection and prevention methodologies to fight against phishing and IoT attacks. In this dissertation, I design a framework, named CrawlPhish, to understand the prevalence and nature of such sophistications, including cloaking, in phishing attacks, which evade detections from the anti-phishing ecosystem by distinguishing the traffic between a crawler and a real Internet user and hence maximize the return-on-investment from phishing attacks. CrawlPhish also detects and categorizes client-side cloaking techniques in phishing with scalability and automation. Furthermore, I focus on the analysis redirection abuse in advanced phishing websites and hence propose mitigations to classify malicious redirection use via machine learning algorithms. Based on the observations from previous work, from the perspective of prevention, I design a novel anti-phishing system called Spartacus that can be deployed from the user end to completely neutralize phishing attacks. Lastly, inspired by Spartacus, I propose iCore, which proactively monitors the operations in the trusted execution environment to identify any maliciousness.

Mobile Augmented Reality (MAR) is a portable, powerful, and suitable technology that integrates 3D virtual content into the physical world in real-time. It has been implemented for multiple intents as it enhances people’s interaction, e.g., shopping, entertainment, gaming, etc. Thus, MAR is expected to grow at a tremendous rate in the upcoming years, as its popularity via mobile devices has increased. But, unfortunately, the applications that implement MAR, hereby referred to as MAR-Apps, bear security issues. Such are imaged in worldwide recorded incidents caused by MAR-Apps, e.g., robberies, authorities requesting banning MAR at specific locations, etc. To further explore these concerns, a case study analyzed several MAR-Apps available in the market to identify the security problems in MAR. As a result of this study, the threats found were classified into three categories. First, Space Invasion implies the intrusive modification through MAR of sensitive spaces, e.g., hospitals, memorials, etc. Then, Space Affectation means the degradation of users’ experience via interaction with undesirable MAR or malicious entities. Finally, MAR-Apps mishandling sensitive data leads to Privacy Leaks. SpaceMediator, a proof-of-concept MAR-App that imitates the well-known and successful MAR-App Pokémon GO, implements the solution approach of a Policy-Governed MAR-App, which assists in preventing the aforementioned mentioned security issues. Furthermore, its feasibility is evaluated through a user study with 40 participants. As a result, uncovering understandability over the security issues as participants recognized and prevented them with success rates as high as 92.50%. Furthermore, there is an enriched interest in Policy-Governed MAR-Apps as 87.50% of participants agreed with restricted MAR-Apps within sensitive spaces, and 82.50% would implement constraints in MAR-Apps. These promising results encourage adopting the Policy-Governed solution approach in future MAR-Apps.

Cyberspace has become a field where the competitive arms race between defenders and adversaries play out. Adaptive, intelligent adversaries are crafting new responses to the advanced defenses even though the arms race has resulted in a gradual improvement of the security posture. This dissertation aims to assess the evolving threat landscape and enhance state-of-the-art defenses by exploiting and mitigating two different types of emerging security vulnerabilities. I first design a new cache attack method named Prime+Count which features low noise and no shared memory needed.I use the method to construct fast data covert channels. Then, I propose a novel software-based approach, SmokeBomb, to prevent cache side-channel attacks for inclusive and non-inclusive caches based on the creation of a private space in the L1 cache. I demonstrate the effectiveness of SmokeBomb by applying it to two different ARM processors with different instruction set versions and cache models and carry out an in-depth evaluation. Next, I introduce an automated approach that exploits a stack-based information leak vulnerability in operating system kernels to obtain sensitive data. Also, I propose a lightweight and widely applicable runtime defense, ViK, for preventing temporal memory safety violations which can lead attackers to have arbitrary code execution or privilege escalation together with information leak vulnerabilities. The security impact of temporal memory safety vulnerabilities is critical, but,they are difficult to identify because of the complexity of real-world software and the spatial separation of allocation and deallocation code. Therefore, I focus on preventing not the vulnerabilities themselves, but their exploitation. ViK can effectively protect operating system kernels and user-space programs from temporal memory safety violations, imposing low runtime and memory overhead.

Utilities infrastructure like the electric grid have been the target of more sophisticated cyberattacks designed to disrupt their operation and create social unrest and economical losses. Just in 2016, a cyberattack targeted the Ukrainian power grid and successfully caused a blackout that affected 225,000 customers.

Industrial Control Systems (ICS) are a critical part of this infrastructure. Honeypots are one of the tools that help us capture attack data to better understand new and existing attack methods and strategies. Honeypots are computer systems purposefully left exposed to be broken into. They do not have any inherent value, instead, their value comes when attackers interact with them. However, state-of-the-art honeypots lack sophisticated service simulations required to obtain valuable data.

Worst, they cannot adapt while ICS malware keeps evolving and attacks patterns are increasingly more sophisticated.

This work presents HoneyPLC: A Next-Generation Honeypot for ICS. HoneyPLC is, the very first medium-interaction ICS honeypot, and includes advanced service simulation modeled after S7-300 and S7-1200 Siemens PLCs, which are widely used in real-life ICS infrastructures.

Additionally, HoneyPLC provides much needed extensibility features to prepare for new attack tactics, e.g., exploiting a new vulnerability found in a new PLC model.

HoneyPLC was deployed both in local and public environments, and tested against well-known reconnaissance tools used by attackers such as Nmap and Shodan's Honeyscore. Results show that HoneyPLC is in fact able to fool both tools with a high level of confidence. Also, HoneyPLC recorded high amounts of interesting ICS interactions from all around the globe, proving not only that attackers are in fact targeting ICS systems, but that HoneyPLC provides a higher level of interaction that effectively deceives them.

Despite an abundance of defenses that work to protect Internet users from online threats, malicious actors continue deploying relentless large-scale phishing attacks that target these users. Effectively mitigating phishing attacks remains a challenge for the security community due to attackers' ability to evolve and adapt to defenses, the cross-organizational nature of the infrastructure abused for phishing, and discrepancies between theoretical and realistic anti-phishing systems. Although technical countermeasures cannot always compensate for the human weakness exploited by social engineers, maintaining a clear and up-to-date understanding of the motivation behind---and execution of---modern phishing attacks is essential to optimizing such countermeasures.

In this dissertation, I analyze the state of the anti-phishing ecosystem and show that phishers use evasion techniques, including cloaking, to bypass anti-phishing mitigations in hopes of maximizing the return-on-investment of their attacks. I develop three novel, scalable data-collection and analysis frameworks to pinpoint the ecosystem vulnerabilities that sophisticated phishing websites exploit. The frameworks, which operate on real-world data and are designed for continuous deployment by anti-phishing organizations, empirically measure the robustness of industry-standard anti-phishing blacklists (PhishFarm and PhishTime) and proactively detect and map phishing attacks prior to launch (Golden Hour). Using these frameworks, I conduct a longitudinal study of blacklist performance and the first large-scale end-to-end analysis of phishing attacks (from spamming through monetization). As a result, I thoroughly characterize modern phishing websites and identify desirable characteristics for enhanced anti-phishing systems, such as more reliable methods for the ecosystem to collectively detect phishing websites and meaningfully share the corresponding intelligence. In addition, findings from these studies led to actionable security recommendations that were implemented by key organizations within the ecosystem to help improve the security of Internet users worldwide.

This dissertation studies three classes of combinatorial arrays with practical applications in testing, measurement, and security. Covering arrays are widely studied in software and hardware testing to indicate the presence of faulty interactions. Locating arrays extend covering arrays to achieve identification of the interactions causing a fault by requiring additional conditions on how interactions are covered in rows. This dissertation introduces a new class, the anonymizing arrays, to guarantee a degree of anonymity by bounding the probability a particular row is identified by the interaction presented. Similarities among these arrays lead to common algorithmic techniques for their construction which this dissertation explores. Differences arising from their application domains lead to the unique features of each class, requiring tailoring the techniques to the specifics of each problem.

One contribution of this work is a conditional expectation algorithm to build covering arrays via an intermediate combinatorial object. Conditional expectation efficiently finds intermediate-sized arrays that are particularly useful as ingredients for additional recursive algorithms. A cut-and-paste method creates large arrays from small ingredients. Performing transformations on the copies makes further improvements by reducing redundancy in the composed arrays and leads to fewer rows.

This work contains the first algorithm for constructing locating arrays for general values of $d$ and $t$. A randomized computational search algorithmic framework verifies if a candidate array is $(\bar{d},t)$-locating by partitioning the search space and performs random resampling if a candidate fails. Algorithmic parameters determine which columns to resample and when to add additional rows to the candidate array. Additionally, analysis is conducted on the performance of the algorithmic parameters to provide guidance on how to tune parameters to prioritize speed, accuracy, or a combination of both.

This work proposes anonymizing arrays as a class related to covering arrays with a higher coverage requirement and constraints. The algorithms for covering and locating arrays are tailored to anonymizing array construction. An additional property, homogeneity, is introduced to meet the needs of attribute-based authorization. Two metrics, local and global homogeneity, are designed to compare anonymizing arrays with the same parameters. Finally, a post-optimization approach reduces the homogeneity of an anonymizing array.

An examination of 12 darkweb sites involved in selling hacking services - often referred to as ”Hacking-as-a-Service” (HaaS) sites is performed. Data is gathered and analyzed for 7 months via weekly site crawling and parsing. In this empirical study, after examining over 200 forum threads, common categories of services available on HaaS sites are identified as well as their associated topics of conversation. Some of the most common hacking service categories in the HaaS market include Social Media, Database, and Phone hacking. These types of services are the most commonly advertised; found on over 50\% of all HaaS sites, while services related to Malware and Ransomware are advertised on less than 30\% of these sites. Additionally, an analysis is performed on prices of these services along with their volume of demand and comparisons made between the prices listed in posts seeking services with those sites selling services. It is observed that individuals looking to hire hackers for these services are offering to pay premium prices, on average, 73\% more than what the individual hackers are requesting on their own sites. Overall, this study provides insights into illicit markets for contact based hacking especially with regards to services such as social media hacking, email breaches, and website defacement.

Cyber-systems and networks are the target of different types of cyber-threats and attacks, which are becoming more common, sophisticated, and damaging. Those attacks can vary in the way they are performed. However, there are similar strategies

and tactics often used because they are time-proven to be effective. The motivations behind cyber-attacks play an important role in designating how attackers plan and proceed to achieve their goals. Generally, there are three categories of motivation

are: political, economical, and socio-cultural motivations. These indicate that to defend against possible attacks in an enterprise environment, it is necessary to consider what makes such an enterprise environment a target. That said, we can understand

what threats to consider and how to deploy the right defense system. In other words, detecting an attack depends on the defenders having a clear understanding of why they become targets and what possible attacks they should expect. For instance,

attackers may preform Denial of Service (DoS), or even worse Distributed Denial of Service (DDoS), with intention to cause damage to targeted organizations and prevent legitimate users from accessing their services. However, in some cases, attackers are very skilled and try to hide in a system undetected for a long period of time with the incentive to steal and collect data rather than causing damages.

Nowadays, not only the variety of attack types and the way they are launched are important. However, advancement in technology is another factor to consider. Over the last decades, we have experienced various new technologies. Obviously, in the beginning, new technologies will have their own limitations before they stand out. There are a number of related technical areas whose understanding is still less than satisfactory, and in which long-term research is needed. On the other hand, these new technologies can boost the advancement of deploying security solutions and countermeasures when they are carefully adapted. That said, Software Defined Networking i(SDN), its related security threats and solutions, and its adaption in enterprise environments bring us new chances to enhance our security solutions. To reach the optimal level of deploying SDN technology in enterprise environments, it is important to consider re-evaluating current deployed security solutions in traditional networks before deploying them to SDN-based infrastructures. Although DDoS attacks are a bit sinister, there are other types of cyber-threats that are very harmful, sophisticated, and intelligent. Thus, current security defense solutions to detect DDoS cannot detect them. These kinds of attacks are complex, persistent, and stealthy, also referred to Advanced Persistent Threats (APTs) which often leverage the bot control and remotely access valuable information. APT uses multiple stages to break into a network. APT is a sort of unseen, continuous and long-term penetrative network and attackers can bypass the existing security detection systems. It can modify and steal the sensitive data as well as specifically cause physical damage the target system. In this dissertation, two cyber-attack motivations are considered: sabotage, where the motive is the destruction; and information theft, where attackers aim to acquire invaluable information (customer info, business information, etc). I deal with two types of attacks (DDoS attacks and APT attacks) where DDoS attacks are classified under sabotage motivation category, and the APT attacks are classified under information theft motivation category. To detect and mitigate each of these attacks, I utilize the ease of programmability in SDN and its great platform for implementation, dynamic topology changes, decentralized network management, and ease of deploying security countermeasures.