Cyber Security Penetration Testing

Penetration Testing & Social Engineering

Penetration testing serves as a pro-active measure to try identify vulnerabilities in services and organizations before other attackers can.

Penetration testing can be offered within many areas, for example:

  • Web applications. There are new web-applications developed and released.
  • Network and Infrastructure. Many applications are not a web-application, but instead uses other protocols. These organization applications can reside both externally and internally.
  • Inside testing / Infected computer simulation. What if a user receives malware on their system? This would be nearly equal to an attacker having hands-on-keyboard on that system, posing a serious risk to any organization.
  • External Organizational Testing. A test which holds within the entire organization as scope for the penetration testers. This is ideal, but often involves having their own internal penetration testing team to focus on this long-term, or high costs involving hiring an external team to do this test.
  • Stolen Laptop Scenario. Further described in our scenarios below.
  • Client Side Applications. Many applications exists in an enterprise written in different languages such as C, C++, Java, Flash, Silverlight or other compiled software. A penetration test could focus on these assets too.
  • Wireless networks. A test which serves to figure out if the WIFI can be broken into, if devices have outdated and vulnerable software, and if proper segmentation has been built between the wireless network and other networks.
  • Mobile applications (Android, Windows Phone, IOS). Mobile applications can have vulnerabilities in them, and also include connections and references to systems hosted inside the enterprise. Mobile applications can also hold secrets such as API keys which can easily be taken advantage of by attackers.
  • Social Engineering. Further described in our scenarios below.
  • Phishing and Vishing. Further described in our scenarios below.
  • Physical. A penetration testing team could try to see what happens if they show up at a location with a laptop and plugs into a network connection. Physical attacks can also include other kinds of covert attacks against locations.
  • ICS ("Industrial Control Systems") / SCADA ("Supervisory Control And Data Acquisition"). These systems typically controls some of the most vulnerable and critical assets in organizations, and as such they should receive scrutiny.

No-knowledge, Partial-knowledge and Full-Knowledge Penetration testing

Depending on the engagement, the organization can decide to give information to the team doing the penetration testing. A no-knowledge penetration, sometimes called a black-box, implies the attacker is given no-knowledge in advance. Partial-knowledge, sometimes called a grey-box test, means the attackers are given some knowledge, and with a full-knowledge penetration test, sometimes called white-box, the penetration testers have everything they need from source-code, network-diagrams, logs and more.

The more information an organization can give the penetration testing team, the higher value the team can provide.

Stolen Laptop Scenario

A great penetration test scenario is to prove the consequences of a stolen or lost laptop. Systems have privileges and credentials on them that attackers could use to get into the target organization.

The system might be protected with a password, but there exists many techniques which may allow the attackers to bypass this protection. For example:

  • The systems hard-drive might not be fully encrypted, allowing an attacker to mount the hard-drive on their own system to extract data and credentials. These credentials could in turn be cracked and re-used across many of the organizations login pages.
  • The user might have locked the system, but a user is still logged in. This user has applications and processes running in the background, even if it is locked. The attackers could try to add a malicious network card to the system via for example USB. This network card tries to become the preferred way for the system to reach the internet. If the system uses this network card, the attackers can now see the network traffic and attempt to find sensitive data, even change data.

As soon as the attackers have access to the system they can start to raid it for information, which can be used to further drive the attackers objectives.

Social Engineering

A system is only as strong as the weakest member, and that is often a human being. Social Engineering involves targeting users with attacks trying to fool them into doing actions they did not intend to. This kind of technique is very popular and many of the biggest hacks in the world has involved using social engineering techniques.

Social Engineering often tries to abuse certain aspects to make victims comply with actions, for example:

  • Most people have the desire to be polite, especially to strangers
  • Professionals want to appear well-informed and intelligent
  • If you are praised, you will often talk more and divulge more
  • Most people would not lie for the sake of lying
  • Most people respond kindly to people who appear concerned about them

When someone has been victimized with a good social engineering attack, they often do not realize they have been attacked at all.

Social Engineering Scenario: Being Helpful

Humans usually wants to be helpful to each other. We like doing nice things!

Consider a scenario where Eve runs into the reception of a big corporate office with her papers soaked in coffee. The receptionist can clearly see Eve in distress and wonders what is going on. Eve explains that she has a job interview in 5 minutes and she really needs her documents printed out for the interview.

In advance Eve has prepared a malicious USB stick with documents designed to compromise computers it is plugged into. She hands the receptionist the malicious USB stick and, with a smile, asks if the receptionist can print the documents for her. This might be what it takes for attackers to infect a system on the internal network, allowing them to compromise(pivot) more systems.

Social Engineering Scenario: Using fear

People often fear of failing or not do as ordered. Attackers will often use fear to try coerce victims into doing what the attackers need. They can for example try to pretend to be the company director asking for information. Perhaps a social media update revealed the director is away on vacation and this can be used to stage the attack.

The victim probably does not want to challenge the director, and because the director is on vacation, it might be harder to verify the information.

Social Engineering Scenario: Playing on Reciprocation

Reciprocation is doing something in return, like a response to someone showing you kindness.

If we consider someone holding the door for you to let you in the front-door of your office building. Because of this, you are likely to want to hold the next door for the person to reciprocate. This door might be behind access-control, needing employees to present their badges, but to offer the same kindness in return, the door is held open. This is called tailgating.

Social Engineering Scenario: Exploiting Curiosity

Humans are curious by nature. What would you do if you found a USB stick lying on the ground out-side the office building? Plug it in? What if the USB stick contained a document with the title "Salary Information - Current Updates"?

An attacker could deliberately drop many malicious USB sticks around the area where employees reside, hoping someone will plug them in.

Documents can contain malicious macros or exploits, or simply trick users into performing certain actions which makes them compromise themselves.


Phishing is a technique usually done through email. Attackers will try to coerce and trick employees into giving away sensitive details such as their credentials or have them install malicious applications giving attackers control of the system.


Phishing is a common technique for attackers to break in, something penetration testers also might try to exploit. It is important to never underestimate the human factor in cyber security. As long as humans involved, phishing will always be a possible way for attackers to gain access to systems.

Phishing should not be used to prove that humans make mistakes, but try prove the consequences of those mistakes. It can also be used to test the strength of anti-spam filters and user awareness.

A campaign of many phishing attempts can be done instead of a single round. A campaign of multiple phishing rounds can help determine the overall awareness of the organization and also let them know that not only attackers are trying to trick our users, but even the security department.


Vishing means to use phone calls to try get unsuspecting employees to perform actions for the attackers. If the employee believes they are in a phone call with someone they know, preferably someone with authority,  the employee can be tricked to performed unwanted actions.


Here is an example where Eve calls Alice:

Eve: Hello, this is Miss Eve calling. I was told to call you personally by the CEO Margarethe; she said you would be able to help.
Alice: Ok... What can I do for you?
Eve: Margarethe is travelling right now, but urgently requests her password to be reset so we can get on with a business meeting happening the moment she lands.
Eve: We urgently request for her email password to be reset so she can deliver the meeting.
Eve: Can you proceed to reset her password to Margareth123?
Alice: I am not sure...
Eve: Please, Margarethe asked for you personally to comply with this request. It must be done now, I don't want to think of the consequences if not...
Alice: Ok. Password is reset

Vishing could try get victims to do information disclosure revealing sensitive information. It could be an attacker asking for a copy of a sensitive document or a spreadsheet.

CS Penetration Testing &Social Engineering