Your Guide to Ransomware Penetration Testing -PlutoSec - Cyber Security Canada
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Ransomware Penetration Testing
Ransomware has raised crisis-level concerns for businesses worldwide. The frequency of ransomware attacks has surged in recent years, with this trend expected to persist over the next decade. In 2021, ransomware damages were estimated at around $20 billion USD, a nearly 60-fold increase from 2015. Damages are projected to reach a staggering $250 billion USD by 2031. The number of ransomware attacks grew by 13 percent compared to 2020, representing 25% of all successful cyber breaches. While healthcare, financial services, and IT were the most affected sectors, ransomware has impacted all industries, including national governments and critical infrastructure.
This guide includes:
The basics of Ransomware Penetration Testing
In response to the escalating ransomware threat, new regulations have been introduced to protect consumer privacy, and there is increased pressure on organizations to demonstrate IT security compliance. This has heightened the demand for evidence of ongoing cybersecurity operations, particularly for obtaining cyber insurance coverage.
Organizations are now reevaluating their IT security measures to find more effective ways to safeguard their assets and ensure operational resilience. A revised approach should include testing an organization’s ability to withstand ransomware attacks. Simulating real-world cyber-attacks that replicate the tactics, techniques, and procedures (TTP) of known ransomware actors provides the most accurate evidence of an organization’s cybersecurity strength. Ransomware-specific penetration testing services identify which systems and data are most likely to be targeted and assess an organization’s ability to defend against and recover from ransomware attacks.
By understanding the threat landscape and exploring strategies to enhance defenses against ransomware, leaders can make more informed decisions about the need for Ransomware Penetration Testing services.
Who Will Benefit From This Guide?
This guide can also assist other IT professionals, including MSPs, IaaS, PaaS, and SaaS providers.
What Is Ransomware Penetration Testing?
Penetration testing involves simulating cyber-attacks on an organization to ensure the effectiveness of security controls, identify and address vulnerabilities within an environment, and provide a detailed attack narrative to evaluate the environment’s cyber-resilience. Penetration testing activities are commonly classified by their objectives into the following types:
Objective-based Penetration Testing – Objective-based Penetration Testing is centered around achieving specific goals, such as gaining access to unauthorized systems or stealing sensitive data. This type of testing mimics an attack by an external threat actor, beginning with an assessment of the security controls that safeguard external attack surfaces.
Infrastructure Penetration Testing – Infrastructure Penetration Testing is aimed at identifying how an attacker might navigate within a LAN, including which sensitive data could be accessed or compromised. This type of testing focuses on tactics such as lateral movement, privilege escalation, and maintaining persistent command and control (C2).
Application Security Testing – Focuses on web, mobile, and native desktop applications to identify exploitable vulnerabilities and safeguard against cyber-attacks.
Ransomware Penetration Testing encompasses a comprehensive penetration test along with both technical and non-technical assessments. These assessments evaluate an organization’s cybersecurity maturity, identify gaps in people, processes, and technology, and test the organization’s ability to respond to and recover from a ransomware attack.
Full Penetration Test – Incorporates relevant activities from PlutoSec’s Objective-Based Penetration Testing (OBPT), Infrastructure Penetration Testing (IPT), and Application Security Testing (AST) service offerings.
Technical Ransomware Assessment – Evaluates the current IT infrastructure to identify potential attack surfaces that ransomware attackers might exploit. This involves a thorough examination of on-premises network and endpoint configurations, cloud application settings, and authentication and encryption protocols. The outcome is a comprehensive list of security vulnerabilities and weaknesses that could make critical systems and data susceptible to ransomware attacks.
Non-technical Ransomware Assessment – Assesses an organization’s administrative policies, controls, and risk strategy, comparing them to industry best practices to gauge its cybersecurity readiness and ability to respond to and recover from ransomware attacks. This evaluation produces a list of observations and recommendations for enhancing defenses against ransomware.
Combining the full penetration test, technical assessment, and non-technical assessment helps estimate the potential impact of known tactics, techniques, and procedures (TTPs) commonly used by ransomware attackers. This approach offers insights that can be directly applied to enhance security policies and controls.
Why is Ransomware Penetration Testing Essential?
Ransomware represents the most significant cyber threat today. Large enterprises have faced financial losses reaching tens of millions of dollars, while small and medium-sized businesses have a high failure rate, with 75% anticipating closure after a successful attack.
Cybersecurity programs rely on security products like malware scanners, next-gen firewalls, content proxies, network intrusion detection and prevention systems (NIDS/NIPS), and endpoint detection and response (EDR) solutions to prevent malware from infiltrating internal networks and executing on endpoints. Ransomware Penetration Testing provides an opportunity to verify that these products are correctly configured to defend against ransomware threats.
Ransomware Penetration Testing offers invaluable evidence-based insights into an organization’s people, processes, and technology, helping to enhance cyber resilience. It ensures that the organization can effectively recover from ransomware attacks, meeting target recovery time objectives (RTO) and recovery point objectives (RPO) to maintain uninterrupted business operations.
What Does Ransomware Penetration Testing Include?
PlutoSec’s Ransomware Penetration Test comprises a comprehensive penetration test, a non-technical ransomware assessment, and a technical ransomware assessment. The full penetration test can be tailored to incorporate relevant elements from PlutoSec’s Objective-Based, Infrastructure, and Application Penetration Testing services. Below, we will outline the non-technical and technical ransomware assessments and explain how they enhance an organization’s security posture against ransomware attacks.
Non-Technical Ransomware Evaluation
The non-technical aspect of a Ransomware Penetration Test adheres to the NISTIR-8374 Ransomware Risk Management framework to gauge an organization’s readiness based on industry best practices and evaluate the potential impact of a ransomware attack. This assessment provides value by engaging a qualified external third party to thoroughly review whether current policies and controls offer adequate protection to meet the organization’s risk objectives. It also examines if these measures effectively minimize the likelihood of a ransomware attack and ensure a robust response and recovery plan if an attack occurs.
The non-technical ransomware assessment involves administrative activities that evaluate the maturity of an organization’s cybersecurity program’s policies and planning:
Technical Ransomware Assessment
The technical component of a Ransomware Penetration Test provides a thorough evaluation of an organization’s ransomware readiness. It assesses whether an attacker can gain access to the target’s systems and data.
Technical assessment activities include:
A Ransomware Penetration Test provides a report detailing the findings of the penetration test, along with additional sections covering the results of the technical and non-technical ransomware preparedness assessments.
What Is RaaS – Ransomware As A Service?
Ransomware as a Service (RaaS) is a criminal enterprise model involving collaboration between two parties: ransomware operators who create and deploy ransomware, and affiliates who target networks, gain initial access, and then pass this access to the operators for ransomware deployment.
RaaS enhances the attackers’ chances of success by splitting the ransomware attack into two distinct phases: the initial phase of gaining access to the target network, and the subsequent phase of encrypting data and demanding a ransom. This division allows each party to specialize and optimize their skills, tools, and operations for their specific stage of the attack process.
The two most common RaaS models are:
Profit sharing model – The ransomware operator deploys the ransomware attack, collects the ransom, and shares a portion of the proceeds with the affiliate who provided initial access to the victim’s network.
Subscription / Flat fee model – Affiliates pay a subscription or one-time fee for a customized ransomware payload, known as a ransomware kit. The affiliate then carries out the attack on their selected target and retains the ransom collected.
Double and Triple Extortion Ransomware
Ransomware typically coerces payment by encrypting a victim’s critical data and demanding a ransom for its decryption. However, this tactic has evolved to include additional forms of extortion, known as double and triple extortion.
**Double extortion** involves not only encrypting the data but also threatening to publicly release the stolen information, which could damage the company’s competitive position or customer trust. **Triple extortion** takes this further by subjecting the organization to ongoing denial-of-service (DOS) attacks, making its websites or other online services inaccessible.
Safeguarding Your Data from Ransomware – Steps You Can Take
Protecting an organization from ransomware relies on robust IT security programs that not only adhere to industry-standard best practices to ensure the Confidentiality, Integrity, and Availability (CIA Triad) of all systems and data but also utilize all available defensive measures. Here are some essential activities to help safeguard your organization from ransomware.
User Awareness Training
Phishing attacks account for over 90% of initial access breaches. Awareness training is crucial in helping employees recognize the tactics and techniques used to infiltrate an organization’s network, which can lead to successful ransomware attacks. This training includes information and exercises designed to help staff identify social engineering tactics, such as malspam, phishing, and spear-phishing, that aim to trick them into executing malware. It is also an opportunity to clarify policies and review standard operating procedures for handling suspicious communications or security incidents.
Network Security Practices
Implementing IT industry standards and best practices throughout an organization’s entire network environment significantly reduces the likelihood of a successful ransomware attack. The NIST Cybersecurity Framework (CSF), NIST Risk Management Framework (RMF), and relevant NIST Special Publication 800 series (SP 800) offer a strong foundation for developing robust and resilient IT infrastructure. Additionally, NISTIR 8374 provides a ransomware-specific guide for enterprises with established cybersecurity programs. For smaller businesses, NIST’s Small-Business Cybersecurity Corner offers an accessible starting point for initiating cybersecurity measures and includes essential ransomware-specific cybersecurity information.
A Bulletproof Backup Strategy
The core backup strategy in the IT industry is the “3-2-1” backup approach. This strategy recommends maintaining at least three copies of all critical files: the original file, a local backup, and an offsite backup. This setup facilitates quick local recovery under typical conditions and provides additional security with offsite backups for emergencies such as ransomware attacks. Additionally, it is crucial to safeguard access to backups with essential security measures, including strong authentication, the principle of least privilege, and multi-factor authentication.
Ongoing Vulnerability Management and Penetration Testing
Vulnerability management is a crucial cybersecurity practice focused on the continuous assessment and tracking of vulnerabilities throughout the network environment. Its primary goal is to identify, remediate, and minimize the window of opportunity for attackers by proactively and consistently uncovering vulnerabilities before they can be exploited. Continuous vulnerability management can be enhanced with a high level of automation to lessen the workload on internal IT teams. Penetration testing provides an additional layer of defense by simulating real-world cyberattacks against the organization. To ensure a comprehensive and reliable assessment, it should be performed by a trusted external third party.
Cyber Insurance and Penetration Testing
Cyber insurance is a method for transferring cyber-risk away from an organization. In the event of a successful attack, it can help cover costs associated with system recovery, business interruption, and legal expenses. Due to the rise in cybercrime, cyber insurance is sometimes required to establish new business partnerships.
Cyber insurance policies often require proof that IT security best practices are implemented, such as firewalls, intrusion detection systems, backups, and encryption. Additionally, policies frequently depend on documented evidence of ongoing cybersecurity measures, including vulnerability management and penetration testing. Penetration tests should be conducted by an independent external service provider to ensure a truly impartial assessment, free from conflicts of interest with the organization’s existing service providers.
However, cyber insurance does not eliminate all risk and responsibility. Recently, cyber insurers have imposed stricter limits on coverage, resulting in higher premiums, increased deductibles, and reduced coverage. Given that completely avoiding responsibility is not feasible, companies should take all possible measures to minimize their attack surface by proactively identifying and addressing security vulnerabilities before attackers can exploit them.
Ransomware Payments: Should You Pay or Not?
In 2021, ransomware payments averaged $100 million per month, and it’s likely that some of this amount is reinvested into developing more sophisticated cyber-attack strategies. Consequently, the FBI and the US Department of Homeland Security advise against paying ransoms. However, if an organization lacks adequate Data-Loss Prevention (DLP) or Disaster Recovery Plans (DRP), paying the ransom might be the only feasible way to recover encrypted files.
Additionally, when attackers use double or triple extortion tactics, companies face heightened risks, even if they manage to recover encrypted data independently. These risks include potential reputational damage, fines due to the exposure of customer data, loss of competitive advantage from published sensitive information, and revenue losses from downtime caused by denial-of-service (DOS) attacks. Such factors can make paying the ransom seem like a viable option.
Other considerations influencing the decision to pay a ransom include whether the organization has sufficient cybersecurity insurance to cover the costs of engaging a third party for recovery and whether there are any sanctions or national security policy embargoes that prohibit making ransom payments to certain entities.
How Does Ransomware Penetration Testing Differ from Other PlutoSec Service Offerings?
PlutoSec’s Ransomware Penetration Testing service encompasses a comprehensive penetration test along with specialized assessments to evaluate an organization’s risk concerning ransomware attacks. This includes both a non-technical ransomware assessment and a technical ransomware assessment. The non-technical assessment is a distinctive component that is exclusively available through the Ransomware Penetration Testing service.
A Ransomware Penetration Testing audit evaluates:
What Is the Cost?
The cost of a penetration test can vary significantly based on the scope and complexity of the engagement. However, the typical range for a high-quality professional service is between $30,000 and $60,000.
The primary factors influencing the cost of a Ransomware Penetration Test include the duration of the engagement, the size and complexity of the target organization’s infrastructure, and the extent of manual testing involved. These aspects are discussed formally between the organization and the penetration testing provider before testing starts.
Organizations considering the value of Ransomware Penetration Testing might initially opt for a narrowly scoped test to evaluate the benefits of penetration testing or include a ransomware assessment as part of an Objective-Based Penetration Test.
The Return on Security Investment (ROSI) The appropriate method for calculating the ROI of penetration testing is the ROSI metric. ROSI (Return on Security Investment) is an alternative ROI calculation tailored to the specific nature of security-related investments. It compares the total avoided costs of potential security breaches to the expenses incurred from penetration testing. A general form of the ROSI equation is:
ROSI = (Security expense avoided – prevention cost) / prevention cost
For instance, if your company anticipates avoiding a minor security breach costing $100,000 over the next year, and the cost of a penetration testing engagement is $10,000, the ROSI calculation would be:
ROSI = ($100,000 – $10,000) / $10,000 = 9
This means the ROSI is 9 times the cost of the penetration test.
What Is Included In A Report?
A Ransomware Penetration Test report is the final deliverable provided by the penetration testing consultant once testing is complete. This report includes a comprehensive overview of findings from any Objective-Based, Infrastructure, or Application Penetration Testing elements, as well as additional sections detailing the results of both technical and non-technical ransomware preparedness assessments.
The report can be used to enhance cybersecurity by addressing identified vulnerabilities and increasing security awareness within the organization by providing context on how these vulnerabilities were exploited.
Reports are organized with identified vulnerabilities prioritized by severity, including evidence of successful exploits such as exfiltrated data, cracked passwords, or screenshots of unauthorized system access.
Following receipt of the pentest report, organizations have the opportunity to ask questions for clarification. They may choose to request further testing or begin the remediation process immediately. It is recommended to conduct additional penetration tests after remediation to ensure that security gaps have been effectively closed.
Who Will Conduct This Test?
The role of a pentester, also known as an ethical hacker, is a specialized IT security position that demands specific training and certification. Ethical hackers can be generalists, with broad skills in various penetration testing techniques, or specialists, with deep expertise in particular areas of the pentesting process. Specialists may focus on specific exploitation frameworks, protocols, operating systems, or types of exploits.
The Offensive Security Certified Professional (OSCP) is a leading and globally recognized certification for ethical hacking, offered by Offensive Security. While Offensive Security provides several certifications, the OSCP is the most comprehensive and well-known. At PlutoSec, our team of skilled ethical hackers holds the industry’s most advanced certifications, with all pentesters required to have at least the OSCP. Many of our team members further enhance their expertise by obtaining additional certifications, including:
This enables our team of OSCP-certified penetration testing professionals to showcase leading-edge, hands-on expertise in penetration testing.

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