Information Gathering #1

Domains and Subdomains:

IP ranges

When not limited to a strictly defined scope, the goal in reconnaissance is to uncover as much information about the target as possible. Identifying additional IP ranges owned by the target can reveal new domains and subdomains, broadening the potential attack surface. This process involves gathering extensive data on the target’s digital footprint, which could lead to uncovering more assets that are relevant for assessment. By expanding the search beyond the initially identified domains, you can uncover a richer set of targets, potentially revealing overlooked or undersecured assets that could be vulnerable to attack. This holistic approach to information gathering is vital for a comprehensive security assessment, allowing for a more effective and thorough evaluation of the target’s security posture.

Infrastructure

To conduct a comprehensive security assessment, it’s crucial to learn as much as possible about the target’s technology stack. Understanding the technologies in use can help identify potential vulnerabilities and plan appropriate attack strategies. Here are key aspects to investigate:

1. Web Application Frameworks:

Determine if the target uses common web frameworks such as ASP.NET, Django, PHP, Flask, etc. Different frameworks have distinct security considerations and potential vulnerabilities.

2. APIs/Web Services:

Identify the types of APIs or web services the target employs. This could include RESTful services, SOAP, GraphQL, and others, each with unique security implications.

3. Content Management Systems (CMS):

Check for the use of CMSs like WordPress, Joomla, Drupal, or DotNetNuke. These platforms often have well-documented vulnerabilities and misconfigurations that can be exploited.

4. Web Servers:

Knowing the web servers (IIS, Nginx, Apache, etc.) and their version numbers is crucial. Outdated servers can contain unpatched vulnerabilities that may be exploited.

5. Back-end Databases:

Identify the databases in use (MSSQL, MySQL, PostgreSQL, SQLite, Oracle, etc.) to understand the possible attack vectors. Each database system has its set of vulnerabilities that can be targeted.

Gathering this information involves a combination of passive and active reconnaissance techniques. Passive methods might include analyzing publicly available information without directly interacting with the target systems, while active methods may involve sending requests to the target and observing the responses to identify technologies and configurations. Tools such as web scanners, network scanners, and specialized frameworks can automate the discovery of technologies and vulnerabilities, aiding in a thorough and efficient assessment process.

Virtual Hosts

Enumerating virtual hosts (vhosts) is a critical step in understanding a target’s infrastructure, particularly when multiple applications are hosted on the same web server. Vhosts allow a single server to host multiple domain names or applications, each potentially having its own distinct web root and configuration. This setup is common in shared hosting environments or when an organization wants to efficiently use server resources.

Vhost enumeration involves identifying these hosted applications and domains, which can reveal additional facets of the target’s online presence that might not be apparent through domain and subdomain enumeration alone. By uncovering vhosts, attackers can expand their understanding of the target’s attack surface, discovering more entry points and potentially vulnerable applications that are not directly linked to the primary domain name.

This enumeration process can uncover applications that are in development, staging versions of live sites, or services that are not intended to be publicly accessible but are inadvertently exposed. Each of these findings presents different angles of attack or areas for further exploration.

Techniques for vhost enumeration may include analyzing DNS records, inspecting web server headers for clues about hosted domains, and employing specialized tools designed to automate the discovery process. Additionally, exploring inconsistencies in web server responses to various host headers can also yield valuable information about the hosted applications.

We’ll delve deeper into the specifics of vhost enumeration techniques and tools later in this module, providing a comprehensive guide to effectively identifying and analyzing virtual hosts as part of a thorough reconnaissance effort.

We can break the information gathering process into two main categories:

Passive information gathering

At this initial stage of reconnaissance, the focus is on passive information gathering, which involves collecting data without directly interacting with the target’s systems. This approach minimizes the risk of detection since it relies on publicly available sources. Here’s how to conduct passive information gathering effectively:

Search Engines: Utilize search engines to find information posted about the target on forums, news articles, job postings, and technical documentation. Advanced search operators can help uncover specific details.

WHOIS Records: WHOIS databases provide registration details of domain names, including the registrant’s contact information, registration dates, and hosting provider. This can help map the target’s online footprint.

Certificate Transparency Logs: SSL/TLS certificates are publicly logged, providing information about subdomains and associated domains. Tools and websites that index these logs can reveal previously unknown domains tied to the target.

DNS Records: Analyzing DNS records, such as A, AAAA, MX, and NS records, can uncover IP addresses, mail servers, and name servers associated with the target, offering insights into their infrastructure.

Social Media and Professional Networks: Profiles and posts on social media and professional networking sites can reveal information about the organization’s employees, technologies in use, and internal projects.

Archived Web Pages: Services like the Wayback Machine allow you to view historical versions of websites, which might contain information that’s no longer available on the current version of the site.

Public Code Repositories: Platforms like GitHub may host source code, configuration files, or documentation that could reveal sensitive information or details about the target’s technology stack and internal processes.

The collected information serves as a foundation for the active information gathering phase, where direct interactions with the target’s systems are performed to validate, expand upon, and exploit the information obtained during passive reconnaissance. By starting with a comprehensive passive phase, you ensure that the active phase is more targeted, efficient, and effective.

Active information gathering

Active information gathering involves directly interacting with the target’s systems to collect data. This phase is more intrusive than passive gathering and can potentially alert the target to the reconnaissance efforts if not conducted carefully. The goal is to confirm, refine, and expand upon the information collected during the passive phase. Here are key techniques used in active information gathering:

1. Port Scanning: Tools like Nmap are used to scan the target’s IP addresses to identify open ports and services running on those ports. This can reveal web servers, mail servers, database services, and other applications that are accessible over the network.

2. Web Server Fingerprinting: This involves sending requests to web servers to determine the server software and version, which can help identify known vulnerabilities. Tools like Wappalyzer or BuiltWith can automate this process.

3. Network Mapping: Beyond identifying open ports, tools can be used to understand the network structure, including firewalls, routers, and other network devices. This helps in planning potential attack vectors.

4. Vulnerability Scanning: Automated tools scan for known vulnerabilities in web applications, server software, and network services. This can highlight weak points in the target’s security posture that could be exploited.

5. Enumeration: Techniques such as DNS zone transfers (if misconfigured), SNMP sweeps, or LDAP queries can provide more details about the network infrastructure, including device names, user accounts, and roles within the network.

6. Web Application Testing: Tools and techniques are used to probe web applications for common vulnerabilities such as SQL injection, cross-site scripting (XSS), and file inclusion vulnerabilities. This also includes testing for misconfigurations and security flaws in custom web applications.

7. Social Engineering: While often considered a separate phase, initial groundwork for social engineering attacks can be part of active gathering. This includes pretexting, phishing simulations, or vishing to gather more information or gain access to systems.

When conducting active information gathering, it’s crucial to have permission from the target organization to avoid legal and ethical issues. This phase is typically more regulated and is part of a sanctioned penetration test or vulnerability assessment.

Properly conducted, active information gathering provides a detailed view of the target’s vulnerabilities and security posture, enabling a more focused and effective penetration testing or security assessment phase.