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Social Engineering A Wolf in Sheep’s Clothing

Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

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Page 1: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Social Engineering

A Wolf in Sheep’s Clothing

Page 2: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 3: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Roberto Salgadou Programmer / Security Researcher / Pentester

u Co-founder of Websec

u Websec = Information Security Solutions

u Pen-testing, training, monitoring, etc…

Contact Infou @LightOS

u [email protected]

u http://www.websec.ca

Page 4: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Overviewu What is Social Engineering?

u Definition

u Brief History

u Trending Topic

u The Evolution of S.E.

u Different Forms of S.E.

u How is Social Engineering Performed?

u Performing OSINT (Open-source Intelligence)

u Selecting a Delivery Method for Payload

u Creating a Command & Control Center

u Making Payload FUD (Fully UnDetectable)

u Live Demo

u How to Defend Against Social Engineering?

Page 5: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Social EngineeringWhat is it?

Page 6: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Definition

u S.E. is an attack vector which involves tricking the human element into breaking security procedures.

u Generally requires very little to NO technological or security knowledge. The very strongest security can be overcome by a clever social engineer.

u Comes in many shapes, forms & colors.

u ALL of us have been victims of it at some point throughout our lives. Affects both end-users and businesses.

Page 7: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Brief History of S.E

u Doesn’t have a defined starting moment.

u Has probably been around since the beginning of humanity.

u Countless examples of S.E. throughout history.

Page 8: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Brief History of S.E - Examplesu Adam & Eve - 4000-6000 BC

u The Trojan Horse - 1188 BC

u George Parker – Early 1900s

u Charles Ponzi – 1920s

u Victor Lustig (“The man who sold the Eiffel Tower”) – 1925

u Frank Abagnale (Catch Me If You Can) – 1960s

u Kevin Mitnick – Around 1980-1995

u Thomas Katona (treasurer of Alcona County, Michigan) – 2007

u Bernie Madoff - 2008

u RSA SecurID Breach – 2011

u AP Twitter Hacked – 2013

u Target (HVAC contractor) - 2013

Page 9: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Brief History of S.E – Personal Examplesu Myself (Gypsies) – 2003?

u Close Friend - 2013

u My Roommate – 2015

u ?

Page 10: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

#SocialEngineering is Trending…

Page 11: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

The Evolution of S.E.u S.E. is no longer confined to the physical realm.

u Technology has made some fraud more difficult to commit, however it's created all sorts of new opportunities for adaptable fraudsters.

u Nigerian phishing scams still work, however not as well as before.

u Attackers have gotten more clever with their techniques.

Page 12: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

The Evolution of S.E.u Receiving an EXE file via e-mail is a thing of the past.

u Ever suspect that an Office document (Word, PowerPoint, Excel) could hack you?

u Heard of HTA? Supported by Windows since 1999.

u Like EXE, but currently undetectable by AV and can run PowerShell

u Unicode magic!

Page 13: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Unicode Magic!

uLeft-To-Right Override

u+U202D

uRight-To-Left Override

u+U202E

Page 14: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Live Demo!

Page 15: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 16: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Different forms of S.E.

u Baiting

u Phishing

u Pretexting

u Tailgating

u Quid Pro Quo

u Shoulder Surfing

u Dumpster Diving

Page 17: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Baiting

u Refers to leaving “bait” for the target to pick up, relying on the curiosity or greed of the person being targeted.

u The Trojan Horse is one of the greatest mythological examples of baiting.

u Modern day example is throwing USBs “Executive Salary Summary Q1 2016”.

u Free Music/Movies for downloading a “game” or providing personal info on a form.

Page 18: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 19: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Baiting

u Send Secretary a bouquet of USB flowers.

u Pretend to be from romantic lover/admirer.

u Curiosity will inevitably lead to the USB flower been plugged in.

u This scenario makes the target be less suspicious of an attack.

Page 20: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Baiting

u According to research, 76% of people plug in an unknown USB to their office computer.

Page 21: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Baiting

u USBs exist that can FRY your computer by just plugging in.

Page 22: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

u Involves fake emails, websites, ads designed to impersonate real systems with the tricking the user.

u One of the more prevalent forms of Social Engineering seen today.

u Fake Anti-Virus infection warning (Scareware), Paypalphishing sites, offers for free music, etc…

Page 23: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

Page 24: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

Page 25: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

Page 26: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

Page 27: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

u Fake SMS message from “Rogers”

u Number 7000 can be spoofed

u Website http://rogers-clients.com/login/

Page 28: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Phishing

Page 29: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Pretextingu Invented scenario to trick victim to perform actions that

normally be unlikely (human equivalent of Phishing)

u Impersonate trustworthy figure: fake IT support needing to do maintenance, false investigator performing a company audit, co-workers, police, tax authorities, etc...

Page 30: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 31: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Pretexting

Page 32: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Quid Pro Quou Means “something for something”.

u A malicious actor calls several IT companies claiming to be

IT service.

u Eventually the attacker will encounter a company that

actually requires the service offered.

Page 33: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Shoulder Surfing

u Looking over someone's shoulder to obtain personal access information.

u Someone's ATM/Smartphone PIN, computer passwords.

u Can be done from a distance too with cameras.

Page 34: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Dumpster Diving

u Involves going through a person/company’s garbage to obtain confidential information.

u Can find bank statements, credit card numbers, contracts, corporate policies, etc..

Page 35: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Social EngineeringHow is it done?

Page 36: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Open-Source Intelligence

u Intel gathered from publically available sources.

u Many platforms available: Google, Facebook, LinkedIn, etc…

u Software available to help: Maltego, theHarvester, creepy, etc…

Page 37: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Delivery Method for Payload

u Several forms: In person, phone, email, website, USB drops.

u E.g.: Pretend to work for their ISP and claim you’ve detected malware installed on their computer.

u Consider what we know about the target.

u Which method would seem the least suspicious?

u Identify your strengths and weaknesses. Practice.

Page 38: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Picking a Domain

u Character omission, repetition, swapping, replacement,

insertion

u Missing dot

u Singularize or pluralize

u Bit flipping

u Homoglyphs

u Wrong TLD

u URLCrazy tool

Page 39: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 40: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Command & Control Center

u Server to host: Load an AWS instance

u Amazon = affordable + trusted IP address

u Different open-source and commercial tools available:

u Metasploit Framework

u PowerShell Empire Framework

u Wide variety of RATs

Page 41: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

MSF C&C

u Free (community edition) & reliable.

u Constantly being improved and added to, has a community contributing stuff.

u Multiplatform.

u Resource Scripts (neat feature to automate).

u Developed and maintained by Rapid7.

Page 42: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Making Payload FUD

u There are many publicly available crypters, packers and code obfuscators.

u Crypters & RATs are shared in online communities, e.g. indectectables.NET

u Mini-Challenges to obtain crypters so they remain FUD for longer.

u Few attack vectors still aren’t well detected (macros, HTAfiles, PowerShell)

Page 43: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 44: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 45: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 46: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Making Payload FUD

Page 47: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

LIVE DEMO

Page 48: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Social EngineeringHow to defend against it?

Page 49: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Am I a target?

u Most definitely!

Page 50: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Heard of Ransomware?

Page 51: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Tips For Staying Safe!

First we have to ask ourselves, why are these techniques so effective?

Carelessness or lack of awareness? Maybe a bit of both…

Page 52: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Tips For Staying Safe!

From Kevin Mitnick’s book “The Art of Deception”:

u People inherently want to be helpful and therefor are

easily duped.

u They assume a level of trust to avoid conflict.

u It’s all about gaining access to information that people

think is innocuous when it isn’t.

u Hear a nice voice over the phone and we want to be

helpful.

Page 53: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Tips For Staying Safe!

u Training & Awareness

u Reminders (Posters)

u Security Hygiene in Office

u Have Policies In-place

u Testing, Testing & More Testing!

u Follow Best Security Practices

u AV?

Page 54: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Tips For Staying Safe!

u Don’t trust what the link shows as the URL, it can be spoofed. Same with file extensions.

<a href="https://www.google.com/" onmousedown="this.href='http://websec.ca'">https://www.google.com/</a>

Page 55: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Don’t Re-use Passwords

u If an attacker obtains your credentials, they may be able to access multiple systems.

u I wrote a tool called “credmap” to test for credential re-use.

u Available at: https://github.com/lightos/credmap

Page 56: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!
Page 57: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Continuity

u Remember it takes patience, time and continuity.

u But keep on fighting off those pesky attackers and you’ll eventually get there!

Page 58: Roberto Salgado Wolf Sheeps Clothing · Brief History of S.E - Examples! Adam & Eve - 4000-6000 BC! The Trojan Horse - 1188 BC! George Parker – Early 1900s! Charles Ponzi – 1920s!

Questions?

Contact Infou @LightOS

u [email protected]

u http://www.websec.ca

Don’t be shy!