An SSL Stripping attack is a form of man-in-the-middle (MITM) attack where an attacker intercepts and alters the communication between a user’s browser and a web server to downgrade HTTPS connections (secure) to HTTP (unsecure). Here’s a step-by-step account of how this attack is typically executed:

Step 1: Target Identification

• Attacker’s Objective: Identify a target, typically a user or a group of users, who are accessing websites that initially start with an HTTP connection before redirecting to HTTPS.
• Tools and Techniques: Use network scanning tools to identify vulnerable websites and users.

Step 2: Network Positioning

• Attacker’s Objective: Position themselves in a location in the network where they can intercept traffic between the target user and the web server.
• Tools and Techniques: Common methods include connecting to the same public Wi-Fi network as the target or using techniques like ARP spoofing on local networks to intercept traffic.
• Understanding the Techniques
• Intercepting Traffic on Public Wi-Fi:
  • How It Works: When a user connects to a public Wi-Fi network, their data transmission may not be encrypted, making it possible for someone on the same network to potentially intercept this data.
  • Potential Tools: Wireshark (for packet analysis), network sniffing tools.
  • Legal and Ethical Use: Only perform network sniffing in a network you own or have explicit permission to analyse.
• ARP Spoofing on Local Networks:
  • How It Works: ARP (Address Resolution Protocol) spoofing involves sending fake ARP messages to a local network. This can allow an attacker to associate their MAC address with the IP address of another host, such as the default gateway, effectively intercepting any traffic meant for that IP address.
  • Potential Tools: Ettercap, dsniff, and ARPspoof.
  • Legal and Ethical Use: This should only be done in a test environment or a network where you have explicit authorization to conduct security tests.
• General Steps in a Controlled Environment
• Setup a Test Environment:
  • Create a controlled lab setting with network devices and machines where you have full permission to conduct tests.
• Select and Configure Tools:
  • Choose appropriate tools for the task. For packet analysis, Wireshark is commonly used. For ARP spoofing, tools like Ettercap can be employed.
  • Configure your tools according to the requirements of your test.
• Conducting the Test:
  • In the case of Wi-Fi sniffing, ensure your network interface is in promiscuous mode to capture traffic.
  • For ARP spoofing, set up your tool to send ARP replies to trick devices into sending traffic through your machine.
• Monitoring and Analysing:
  • Monitor the traffic and analyse it for educational purposes.
  • Understand the patterns and vulnerabilities associated with unsecured networks.
• Implementing Countermeasures:
  • Use this knowledge to implement security measures, such as strong encryption (WPA2/WPA3) for Wi-Fi and static ARP tables to prevent spoofing.

Step 3: Intercepting the Connection

• Attacker’s Objective: Intercept the initial HTTP request from the user to the web server.
• Tools and Techniques: Utilize packet sniffing tools (like Wireshark) to monitor and capture network traffic.

Step 4: SSL Stripping

• Attacker’s Objective: Modify the HTTP response from the web server to prevent the redirection to the HTTPS site.
• Tools and Techniques: Employ an SSL stripping tool or script that removes the HTTPS redirect commands from the server’s response, forcing the user to stay on an unencrypted HTTP connection.
• Nmap (Network Mapper)
  • Description: A powerful and versatile tool for network discovery and security auditing. Nmap is used to discover devices running on a network and the services they are running.
  • Acquisition: Available for free from Nmap’s official website.
• Wireshark
  • Description: A network protocol analyzer that lets you capture and interactively browse the traffic running on a computer network.
  • Acquisition: Can be downloaded for free from Wireshark’s official website.
• Angry IP Scanner
  • Description: A fast and friendly network scanner that is used for network monitoring and managing the connected devices on your network.
  • Acquisition: Available for free from Angry IP Scanner’s website.
• Advanced IP Scanner
  • Description: A free, fast, and powerful network scanner with a user-friendly interface, used for analysis of local networks.
  • Acquisition: Can be downloaded from Advanced IP Scanner’s official site.
• Zenmap
  • Description: The official Nmap Security Scanner GUI, Zenmap is suitable for beginners while providing advanced features for experienced Nmap users.
  • Acquisition: Downloadable from Nmap’s official website.
• Nessus
  • Description: Nessus is one of the most comprehensive and widely deployed vulnerability assessment tools. It scans for vulnerabilities and does compliance checks.
  • Acquisition: Available from Tenable, the Nessus developer.
• Netcat
  • Description: Known as the “Swiss-army knife” of networking, it is a versatile utility that reads and writes data across network connections.
  • Acquisition: Comes pre-installed on many Linux distributions; Windows version available at Netcat’s GitHub repository.
• Tcpdump
  • Description: A powerful command-line packet analyzer; used to capture or filter TCP/IP packets that are received or transferred over a network.
  • Acquisition: Pre-installed on most Unix/Linux systems; more information available at Tcpdump’s official website.
• SolarWinds Network Performance Monitor
  • Description: A comprehensive network performance monitor that can detect, diagnose, and resolve network performance issues.
  • Acquisition: Available from SolarWinds’ official website.
• Fing
  • Description: A network scanner that provides you with detailed information about the devices connected to your network.
  • Acquisition: Downloadable from Fing’s official website.

Step 5: Establishing Proxy Connection

• Attacker’s Objective: Create a proxy connection that allows the attacker to receive and modify the communication between the user and the web server.
• Tools and Techniques: Set up a proxy server to relay traffic between the user and the actual web server, modifying or capturing the data as needed.
• Setting Up a Proxy Server for Educational Purposes
• 1. Setting Up a Test Environment:
• Ensure you have permission to set up and use a proxy in your network.
• Use isolated network environments like a lab setup for testing.
• 2. Choosing a Proxy Server Software:
• Select a proxy server software suitable for educational purposes. Tools like Squid, Burp Suite (for web application testing), or OWASP ZAP can be used.
• 3. Installing the Proxy Server:
• Install the proxy server software on a machine that can intercept traffic. For example, for Squid:arduinoCopy codesudo apt-get install squid
• 4. Configuring the Proxy Server:
• Configure the proxy server settings according to your requirements. This includes setting up rules for handling incoming and outgoing traffic, access controls, and logging options.
• For educational purposes, you might want to set up the proxy to log traffic for analysis without modifying it.
• 5. Setting Up Client Machines:
• Configure client machines to route traffic through the proxy server. This is usually done by setting the proxy server’s IP address and port in the network settings of the client.
• 6. Monitoring and Analysing Traffic:
• Monitor the traffic passing through the proxy server. Use this opportunity to learn about network traffic patterns, HTTP requests and responses, and other networking concepts.
• 7. Implementing Security Measures:
• Learn how to implement security measures like SSL/TLS encryption to protect against MITM attacks in real-world scenarios.
• 8. Legal and Ethical Considerations:
• Remember, intercepting or modifying network traffic without proper authorization is illegal. Use this setup only in a legal and ethical manner.
• Step 1: Setting Up the Proxy Server
• Explanation: “First, an attacker sets up a proxy server. This server acts as an intermediary between the user’s device and the internet. Tools like Burp Suite or OWASP ZAP can be configured to act as proxies.”
• Step 2: Intercepting the Traffic
• Explanation: “With the proxy in place, the next step is traffic interception. This requires the attacker to be in a position to direct internet traffic through their proxy. Techniques like ARP spoofing or DNS poisoning in a local network can be used to achieve this.”

Step 6: Data Capture and Manipulation

• Attacker’s Objective: Capture sensitive data like login credentials, personal information, or financial data sent over the unencrypted HTTP connection.
• Tools and Techniques: Use custom scripts or tools to capture and log the data passing through the proxy server. The attacker can also manipulate data being sent to the server.
• Step 3: Capturing the Data
• Explanation: “Once the traffic flows through the proxy, the attacker can capture it. Tools like Wireshark can be used alongside the proxy to log the traffic. These tools capture packets that can be analysed later.”
• Step 4: Analysing the Captured Data
• Explanation: “Analysis involves inspecting the captured data for sensitive information like credentials, session tokens, or personal data. This step requires a good understanding of network protocols and data patterns.”
• Step 5: Data Manipulation (If Applicable)
• Explanation: “In some cases, an attacker may not only capture but also manipulate the data. This could be altering requests or responses to inject malicious code or to redirect users to fraudulent sites.”

Step 7: Maintaining Stealth

• Attacker’s Objective: Conduct the attack without being detected by either the user or the web server.
• Tools and Techniques: Employ various obfuscation techniques to hide malicious activity, including mimicking regular traffic patterns and using encryption to hide the attack traffic from network security tools.

Step 8: Ending the Attack

• Attacker’s Objective: End the attack without leaving traces.
• Tools and Techniques: Clean up any changes made to the user’s or network’s configuration, remove logs, and disconnect from the network.

Countermeasures

• For Users: Always verify the URL to ensure it’s HTTPS, particularly before entering sensitive information. Use browser extensions that force HTTPS connections.
• For Webmasters: Implement HTTP Strict Transport Security (HSTS) to ensure that browsers always establish a secure connection, even if the user initially requests HTTP.

Ethical and Legal Considerations

• Important Note: Conducting an SSL stripping attack without explicit permission is illegal and unethical.