1. Introduction
Testing the security of a new Microsoft Windows Server 2019 system is crucial to ensure the protection of sensitive information and prevent potential breaches. There are several methods that can be employed to test the security of the system, including vulnerability scanning, penetration testing, configuration review, log analysis, and compliance testing. These methods use automated tools such as Nessus, Metasploit, and Splunk to identify vulnerabilities, simulate attacks, and monitor for suspicious activity.
2. Test the security of a new Microsoft Windows Server 2019 system
To test the security of a new Microsoft Windows Server 2019 system, some methods that can be employed include:
Vulnerability scanning: Using automated tools to scan the system for known vulnerabilities and weaknesses. This can include using software such as Nessus , OpenVAS, and Qualys to identify vulnerabilities in the system’s operating system, applications, and network configurations.
Penetration testing: Attempting to exploit vulnerabilities found during vulnerability scanning to assess the system’s overall security posture. This can include using software such as Metasploit , Core Impact , and Nmap to simulate an attack on the system and identify vulnerabilities that can be exploited by an attacker.
Configuration review: Reviewing the system’s configuration and settings to ensure that they are secure and comply with industry best practices. This can include reviewing settings such as password policy, firewall configuration, and user permissions, using tools such as Microsoft Security Compliance Toolkit and Microsoft Baseline Security Analyzer
Log analysis: Analyzing system and network logs to identify any suspicious activity that could indicate an attempted or successful attack. This can include using software such as Splunk , LogRhythm , and Elasticsearch to monitor logs for patterns of malicious activity.
Compliance testing: Testing the system to ensure that it complies with industry standards and regulations, such as HIPAA, PCI-DSS, and NIST. This can include using tools such as Nessus Compliance Checks, OpenSCAP , and Tenable.sc
Some examples of brute force or dictionary attacks seen in real-world scenarios include:
In 2020, a brute force attack was launched against a large number of WordPress sites, attempting to guess the admin password using a dictionary of common words and phrases.
In 2018, a brute force attack was launched against the login page of a popular online retailer, attempting to guess the password using a list of commonly used passwords.
In 2016, a dictionary attack was launched against a financial institution, attempting to guess the password of online banking users by using a list of commonly used words and phrases.
2. Methodology to be used
When testing the security of a new Microsoft Windows Server 2019 system, I would use a combination of both automated and manual testing methods to ensure a comprehensive assessment of the system’s security posture.
First, I would use automated vulnerability scanning tools such as Nessus, OpenVAS, and Qualys to identify vulnerabilities in the system’s operating system, applications, and network configurations.
Next, I would conduct a penetration test using tools such as Metasploit , Core Impact , and Nmap to simulate an attack on the system and identify vulnerabilities that can be exploited by an attacker.
I would also review the system’s configuration and settings to ensure that they are secure and comply with industry best practices. I would use tools such as Microsoft Security Compliance Toolkit and Microsoft Baseline Security Analyzer to check the configuration settings such as password policy, firewall configuration, and user permissions.
I would also analyze system and network logs using tools such as Splunk, LogRhythm, and Elasticsearch to identify any suspicious activity that could indicate an attempted or successful attack.
Compliance testing would be done using tools such as Nessus Compliance Checks, OpenSCAP, and Tenable.scto ensure that the system complies with industry standards and regulations such as HIPAA, PCI-DSS, and NIST.
The methodology I would use is known as the “Penetration testing execution standard (PTES)” which is a comprehensive framework for performing penetration testing. This methodology covers the entire process of penetration testing, from initial reconnaissance to reporting, with clear guidelines and best practices for each step. This approach allows for a consistent and thorough testing process that can identify vulnerabilities and provide actionable recommendations
3. Types of Attacks that can be modeled
When conducting a penetration test, I would model various types of attacks to simulate real-world scenarios and assess the system’s ability to defend against them. Some examples of attacks that I would model include:
External network attacks: These attacks target the system from outside the organization’s network, such as through the Internet. Examples include port scanning, network mapping, and exploiting vulnerabilities in web applications and services.
Internal network attacks: These attacks target the system from within the organization’s network, such as from an infected endpoint or a compromised user account. Examples include exploiting vulnerabilities in internal systems, privilege escalation, and lateral movement.
Social engineering attacks: These attacks target the users of the system, rather than the system itself, through tactics such as phishing, vishing, and baiting.
Wireless network attacks: These attacks target wireless networks and devices, such as Wi-Fi routers and access points. Examples include exploiting vulnerabilities in wireless protocols, cracking WPA/WPA2 encryption, and spoofing wireless access points.
Application-layer attacks: These attacks target specific applications and services running on the system, such as web applications and databases. Examples include SQL injection, cross-site scripting (XSS), and remote code execution (RCE)
Advanced persistent threat (APT) attacks: These attacks target a specific organization and are typically carried out by a skilled and well-resourced attacker, with the goal of maintaining long-term access to the system. Examples include spear-phishing, malware, and use of zero-day vulnerabilities.
4. Common Exploits
An attacker could exploit a system in several ways, some common methods include:
Exploiting known vulnerabilities: Attackers can use known vulnerabilities in the system’s operating system, applications, and network configurations to gain access or execute malicious code. To test for this, I would use automated vulnerability scanning tools such as Nessus , OpenVAS , and Qualys to identify these vulnerabilities.
Social engineering: Attackers can trick users into providing sensitive information or executing malicious code by using tactics such as phishing, vishing, and baiting. To test for this, I would conduct social engineering assessments, such as phishing campaigns, to evaluate the susceptibility of users to these types of attacks.
Remote code execution (RCE): Attackers can execute arbitrary code on the system by exploiting vulnerabilities in web applications, services, or operating systems. To test for this, I would use automated web application scanners such as Burp Suite or manual penetration testing techniques, such as injecting malicious code into user inputs.
Lateral movement: Attackers can move laterally within a network, once they have gained access to a system, by exploiting vulnerabilities in network protocols or by using stolen credentials. To test for this, I would use penetration testing tools such as Metasploit or Cobalt Strike to simulate lateral movement scenarios.
Advanced persistent threats (APT): Attackers can target a specific organization and maintain long-term access to the system by using techniques such as spear-phishing, malware, and zero-day vulnerabilities. To test for this, I would use advanced threat detection and response tools, such as Carbon Black or Crowdstrike
5. Conclusion
The security of a new Microsoft Windows Server 2019 system can be effectively tested by using a combination of both automated and manual testing methods. The methodology known as the “Penetration testing execution standard (PTES)” can be used as a comprehensive framework for performing penetration testing, covering the entire process from initial reconnaissance to reporting. By using the combination of these methods, it can identify vulnerabilities and potential weaknesses in the system, prevent potential breaches and ensure compliance with industry standards and regulations.
References:
- OWASP Testing Guide
- NIST Special Publication 800-115: Technical Guide to Information Security Testing and Assessment
- SANS Institute: Penetration Testing Methodologies
- Nessus: https://www.tenable.com/products/nessus
- OpenVAS: https://www.openvas.org/
- Qualys: https://www.qualys.com/
- Metasploit: https://www.metasploit.com/
- Core Impact: https://www.coresecurity.com/core-impact
- Nmap: https://nmap.org/
- Microsoft Security Compliance Toolkit: https://www.microsoft.com/en-us/download/details.aspx?id=55319
- Microsoft Baseline Security Analyzer: https://www.microsoft.com/en-us/download/details.aspx?id=7558
- Splunk: https://www.splunk.com/
- LogRhythm: https://www.logrhythm.com/
- Elasticsearch: https://www.elastic.co/
- Nessus Compliance Checks: https://www.tenable.com/compliance/nessus-compliance-checks
- OpenSCAP: https://www.open-scap.org/
- Tenable.sc: https://www.tenable.com/products/tenable-sc
- Burp Suite: https://portswigger.net/burp
- Cobalt Strike: https://www.cobaltstrike.com/
- Carbon Black: https://www.carbonblack.com/
- Crowdstrike: https://www.crowdstrike.com/