Penetration Testing | ICSS Student | Rakesh Mondal

Penetration Testing

Penetration testing, also known as a pen test, is a simulated cyberattack against your computer system to check for exploitable vulnerabilities. In the context of web application security, penetration testing is commonly used to augment a web application firewall (WAF).

Penetration testing can involve the attempted breaching of any number of application systems, (e.g., application protocol interfaces (APIs), frontend/backend servers) to uncover vulnerabilities, such as unsanitized inputs that are susceptible to code injection attacks.

Penetration testing project done by ICSS Student Rakesh Mondal. The full project discussed below:


Project Name: Penetration testing

Author Name: Rakesh Mondal

Publish Date:  12-07-2018


What is Penetration Testing?

  • An attack on a computer system with the intention of finding security weaknesses
  • Used to determine the feasibility of a set of attacks
  • Used to identity security vulnerabilities
  • Testing the ability of network defenders to respond to attacks
  • Can be used to help security
  • Used by security professionals to harden systems


Penetration Testing


Steps to Penetration Testing


  • Start with list of potential vulnerabilities
  • Possible open ports, old software, or week passwords
  • Rank the list in order of criticality.
  • Most damaging possible attack to least
  • Device a test for each possible vulnerability.
  • Port scans, password crackers, find software versions.
  • Run tests on possible vulnerabilities.
  • Fix issues that were found.




Penetration Testing Tools


  • Kali Linux
  • Nmap, Fragrouter, Fern Wifi Cracker, HydraGTK
  • Websites
  • Port scanners, web vulnerability checkers, DNS checkers
  • Metasploit
  • Exploit tester, GUI interface, test web apps and networks
  • Wireshark
  • Monitor network traffic, packets
  • W3af
  • Web attack and audit framework




What is Kali Linux?


  • Advanced penetration testing and security auditing linux distribution
  • 300+ build in penetration testing tools
  • Free / Open source
  • FHS (File Hierarchy Standard) compliant
  • Secure development environment
  • Spin off of Backtrack


Kali Linux


Using Kali Linux


  • Install to hard disk
  • 10 GB disk space
  • USB / CD-DVD
  • Live USB Install
  • 2GB capacity
  • Win32 Disk Imager
  • Android 2.1 + devices
  • 5 GB free space
  • Network install
  • Virtual Machine
  • Run in side another OS


hard disk


Included Kali Tools


  • Information Gathering
  • Dnsdict6
  • Nmap
  • Urlcrazy
  • IDS/IPS (Intrusion Detection/Protection System)
  • Fragrouter
  • Network Scanners
  • Dnmap
  • Netdiscover
  • Traffic Analysis
  • Intrace
  • Vulnerability Analysis
  • Cisco tools
  • Yersinia
  • Web Vulnerability Scanner
  • ProxyStrike
  • Cadaver
  • Wireless Attacks
  • Bluelog
  • Spooftooph
  • Wireless Tools
  • Aircrack








Information Gathering Tools DNSDICT6


  • Finds all sub-domains of a website or web server
  • Enumerates all IPv4 and IPv6 addresses to extract dumps
  • Sub-domains
  • IP information
  • Powerful for extracting sub domains that are restricted
  • Tutorials Online
  • Google
  • Youtube





Information Gathering Tools Nmap


  • Security Scanner
  • Gordon Lyon
  • Discovers hosts and services on a computer network and creates a map of the network
  • Special Packets
  • Analyzes reponses
  • Host discovery
  • Service discovery
  • Operating system detections





IDP / IPS Fragrouter


  • Intercepts, Modifies, and rewrites traffic destined for a specified host
  • Routes network traffic in a way that eludes IDS
  • Uses
  • Test IDS timeout and reassembly
  • Test TCP/IP scrubbing
  • Test firewalls
  • Evade Passive OS fingerprinting


IPS Fragrouter


Network Scanners DNMap


  • Framework for distributing nmap scans among many clients
  • Client/Server architecture
  • Server knows what to do
  • Clients do it
  • Clients work when server is offline
  • Real time statistics of the clients and their targets
  • Scans very large networks quickly





Traffic Analysis Intrace


  • Works along the same lines as Fragrouter
  •  Enumerates IP hops exploiting TCP connections to display the path of packets over the network
  • Network reconnaissance
  • Who is connected to who
  • Firewall bypassing





Vulnerability Analysis Cisco Auditing Tool


  • Perl script that scans cisco routers for common vulnerabilities
  • Default passwords, usernames
  • Easy to guess names and passwords
  • IOS bug history
  • Hijack a router
  • Test router security
  • Password
  • Username






Web Vulnerability Scanner ProxyStrike


  • Active web application proxy designed to find vulnerabilities while browsing a web application
  • Mainly javascript
  • Sql injection and XSS plugins
  • Listens to port 8008 and analyzes all the parameters of applications running in the port for vulnerabilities







  • Security focused Linux Distribution
  • 300+ security tools
  • Spin off of popular backtrack
  • Multiple ways to run
  • Hard drive
  • USB / Live CD
  • Virtual Machine
  • Detailed Look at some tools
  • To many to cover them all



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