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Phishing: It’s Not Just for Pentesters
Using Phishing to Build a Successful Awareness Program
Intro
www.hackerhalted.com 2
• Enterprise Security Consultant at Sword & Shield Enterprise Security
• 2017 DerbyCon Social Engineering Capture the Flag (SECTF) winner
• Served in the US Navy, Navigating Submarines
• Holds the CISSP-ISSMP, GSNA, and GCIH certifications
• Frequent Guest Blogger
• AlienVault
• Tripwire
• ITSP Magazine
• Sword & Shield’s Blog
• Maintains blog and podcast at https://advancedpersistentsecurity.net
• Trains (spoken taps out a lot) in Brazilian Jiu Jitsu
www.hackerhalted.com 3
Goals
www.hackerhalted.com 4
• Open Source Intelligence (OSINT)
• Social Engineering
• Pretexting
• *ishing (Spear phishing,Vishing, and Smishing)
• Whaling
• Baiting
• Dumpster Diving
• Applied Social Engineering
• OSINT in enabling more effective social engineering
• Tools andTechniques for collecting OSINT
• OSINT and Social Engineering integration
• Mitigations of Social Engineering
• Training ofTeams
What is Social Engineering?
www.hackerhalted.com 5
• Human Hacking
• Exploits the human factor and often bypasses technology and
expensive equipment
Pioneers of the Art
www.hackerhalted.com 6
www.hackerhalted.com 7
Examples of Social Engineering
www.hackerhalted.com 8
• Phishing
• Spear Phishing
• Whaling
• Vishing
• Smishing
• Baiting
• Pretexting
• Dumpster Diving
• Tailgating
Psychology of Social Engineering
www.hackerhalted.com 9
• Everything goes back to Dr. Cialdini’s 6 Principles of Persuasion
1. Reciprocity
2. Commitment and Consistency
3. Social Proof
4. Liking (Likability)
5. Authority
6. Scarcity (Urgency)
Applicationof Social Engineering
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• Social Engineering aims to influence the users to:
• Provide some sort of data (ideally, sensitive data)
• Tell us something that is not online and readily available
• Tell us who could do something or tell us more (give us better targets)
• Tell us about the operating environment and issues within
• Perform an action
• Clicking a link
• Making a change to the firewall rules
• Open an email
What is OSINT?
www.hackerhalted.com 11
OSINT is drawn from publicly available material, including:
• The Internet
• Traditional mass media (e.g. television, radio,
newspapers, magazines)
• Specialized journals, conference proceedings, and think
tank studies
• Photos
• Geospatial information (e.g. maps and commercial
imagery products)
Where can one gather OSINT?
www.hackerhalted.com 12
Gathering OSINT
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• Public conversations (borderline HUMINT)
• Bars
• Malls
• Restaurants
• Family and Friends
• BackWindshields
• Mostly, the internet
• Forums
• Job Boards
• Search Engines
• Social Media
Goals of OSINT
www.hackerhalted.com 14
An example of OSINT
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Another Example
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…another…
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…last one…
www.hackerhalted.com 18
OSINT Demo
www.hackerhalted.com 19
Timing
www.hackerhalted.com 20
SE and OSINT Relationship
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• They share similar properties in terms of human psychology
• OSINT can be used to build a dossier or profile about a SE target
• This can provide context for the contact
• Better pretexting
• Better (spear) phishing
• Better “other” technical stuff like password guess (or even
passwords)
Attribution?
www.hackerhalted.com 22
Law Enforcement
www.hackerhalted.com 23
Sales and Retail
www.hackerhalted.com 24
…more examples…
www.hackerhalted.com 25
…even more…
www.hackerhalted.com 26
Is this one and done?
• Several rounds may be required.
• You may find something interesting towards the end that
causes you to look at everything again from a different angle.
www.hackerhalted.com 27
Collection Considerations
• What is the Endgame?
• Is what you’re doing ethical?
• Do you have an ethical obligation to do this a certain way?
• Is this legal?
• Does the state that I am doing this in require Private
Investigator Licensure?
• I have collected all this data, how do I protect it?
• How long do I retain it?
• How do I dispose of it?
• What value could be assigned to it?
www.hackerhalted.com 28
Weaponizing OSINT
• We can’t be like the South Park underpants gnomes…
www.hackerhalted.com 29
Social Engineering Demo
www.hackerhalted.com 30
Contact Me
Social Media
• Twitter: @C_3PJoe / @advpersistsec
• LinkedIn: linkedin.com/in/billyjgrayjr
• Facebook: facebook.com/joegrayinfosec
Email
• jgray@advancedpersistentsecurity.net
• bjg@swordshield.com
Blog and Podcast
• advancedpersistentsecurity.net
Podcast is also on iTunes, Stitcher, Google Play, and other fine platforms
www.hackerhalted.com 31
Future Speaking Engagements
October 17-18: EDGE Security Conference, Knoxville, TN
October 20-22: SkyDogCon, Nashville, TN
October 26-17: Lone Star Application Security Conference
(LASCON), Austin, TX
November 11: Bsides Charleston, Charleston, SC
November 15: Metro Atlanta ISSA Conference, Atlanta, GA
www.hackerhalted.com 32
Contacting Sword & Shield
www.hackerhalted.com 33
Questions?
www.hackerhalted.com 34
OSINT Resources
35
(All in no particular order; except the book section)
• Blogs:
• Automatingosint.com
• learnallthethings.net
• Osint.fail
• Podcasts:
• Complete and Privacy Security Podcast
• Social Engineer Podcast
• Book:
• Open Source IntelligenceTechniques (Michael Bazzell)
• Slack:
• Openosint.slack.com
• Aps-opensource.signup.team
OSINT Resources
36
(All in no particular order; except the book section)
• People to Follow:
• @beast_fighter
• @baywolf88
• @jms_dot_py
• @jnordine
• @upgoingstar
• @_sn0ww
• @sarahjamielewis
• @webbreacher
• @andrewsmhay
• @dutch_osintguy
• @infosecsherpa
• @sweet_grrl
• @inteltechniques
• @cybersecstu
• @jennyradcliffe
• @ginsberg5150
• @iv_Machiavelli
• @GRC_Ninja

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Phishing: It’s Not Just for Pentesters Using Phishing to Build a Successful Awareness Program

  • 1. Phishing: It’s Not Just for Pentesters Using Phishing to Build a Successful Awareness Program
  • 2. Intro www.hackerhalted.com 2 • Enterprise Security Consultant at Sword & Shield Enterprise Security • 2017 DerbyCon Social Engineering Capture the Flag (SECTF) winner • Served in the US Navy, Navigating Submarines • Holds the CISSP-ISSMP, GSNA, and GCIH certifications • Frequent Guest Blogger • AlienVault • Tripwire • ITSP Magazine • Sword & Shield’s Blog • Maintains blog and podcast at https://advancedpersistentsecurity.net • Trains (spoken taps out a lot) in Brazilian Jiu Jitsu
  • 4. Goals www.hackerhalted.com 4 • Open Source Intelligence (OSINT) • Social Engineering • Pretexting • *ishing (Spear phishing,Vishing, and Smishing) • Whaling • Baiting • Dumpster Diving • Applied Social Engineering • OSINT in enabling more effective social engineering • Tools andTechniques for collecting OSINT • OSINT and Social Engineering integration • Mitigations of Social Engineering • Training ofTeams
  • 5. What is Social Engineering? www.hackerhalted.com 5 • Human Hacking • Exploits the human factor and often bypasses technology and expensive equipment
  • 6. Pioneers of the Art www.hackerhalted.com 6
  • 8. Examples of Social Engineering www.hackerhalted.com 8 • Phishing • Spear Phishing • Whaling • Vishing • Smishing • Baiting • Pretexting • Dumpster Diving • Tailgating
  • 9. Psychology of Social Engineering www.hackerhalted.com 9 • Everything goes back to Dr. Cialdini’s 6 Principles of Persuasion 1. Reciprocity 2. Commitment and Consistency 3. Social Proof 4. Liking (Likability) 5. Authority 6. Scarcity (Urgency)
  • 10. Applicationof Social Engineering www.hackerhalted.com 10 • Social Engineering aims to influence the users to: • Provide some sort of data (ideally, sensitive data) • Tell us something that is not online and readily available • Tell us who could do something or tell us more (give us better targets) • Tell us about the operating environment and issues within • Perform an action • Clicking a link • Making a change to the firewall rules • Open an email
  • 11. What is OSINT? www.hackerhalted.com 11 OSINT is drawn from publicly available material, including: • The Internet • Traditional mass media (e.g. television, radio, newspapers, magazines) • Specialized journals, conference proceedings, and think tank studies • Photos • Geospatial information (e.g. maps and commercial imagery products)
  • 12. Where can one gather OSINT? www.hackerhalted.com 12
  • 13. Gathering OSINT www.hackerhalted.com 13 • Public conversations (borderline HUMINT) • Bars • Malls • Restaurants • Family and Friends • BackWindshields • Mostly, the internet • Forums • Job Boards • Search Engines • Social Media
  • 15. An example of OSINT www.hackerhalted.com 15
  • 21. SE and OSINT Relationship www.hackerhalted.com 21 • They share similar properties in terms of human psychology • OSINT can be used to build a dossier or profile about a SE target • This can provide context for the contact • Better pretexting • Better (spear) phishing • Better “other” technical stuff like password guess (or even passwords)
  • 27. Is this one and done? • Several rounds may be required. • You may find something interesting towards the end that causes you to look at everything again from a different angle. www.hackerhalted.com 27
  • 28. Collection Considerations • What is the Endgame? • Is what you’re doing ethical? • Do you have an ethical obligation to do this a certain way? • Is this legal? • Does the state that I am doing this in require Private Investigator Licensure? • I have collected all this data, how do I protect it? • How long do I retain it? • How do I dispose of it? • What value could be assigned to it? www.hackerhalted.com 28
  • 29. Weaponizing OSINT • We can’t be like the South Park underpants gnomes… www.hackerhalted.com 29
  • 31. Contact Me Social Media • Twitter: @C_3PJoe / @advpersistsec • LinkedIn: linkedin.com/in/billyjgrayjr • Facebook: facebook.com/joegrayinfosec Email • jgray@advancedpersistentsecurity.net • bjg@swordshield.com Blog and Podcast • advancedpersistentsecurity.net Podcast is also on iTunes, Stitcher, Google Play, and other fine platforms www.hackerhalted.com 31
  • 32. Future Speaking Engagements October 17-18: EDGE Security Conference, Knoxville, TN October 20-22: SkyDogCon, Nashville, TN October 26-17: Lone Star Application Security Conference (LASCON), Austin, TX November 11: Bsides Charleston, Charleston, SC November 15: Metro Atlanta ISSA Conference, Atlanta, GA www.hackerhalted.com 32
  • 33. Contacting Sword & Shield www.hackerhalted.com 33
  • 35. OSINT Resources 35 (All in no particular order; except the book section) • Blogs: • Automatingosint.com • learnallthethings.net • Osint.fail • Podcasts: • Complete and Privacy Security Podcast • Social Engineer Podcast • Book: • Open Source IntelligenceTechniques (Michael Bazzell) • Slack: • Openosint.slack.com • Aps-opensource.signup.team
  • 36. OSINT Resources 36 (All in no particular order; except the book section) • People to Follow: • @beast_fighter • @baywolf88 • @jms_dot_py • @jnordine • @upgoingstar • @_sn0ww • @sarahjamielewis • @webbreacher • @andrewsmhay • @dutch_osintguy • @infosecsherpa • @sweet_grrl • @inteltechniques • @cybersecstu • @jennyradcliffe • @ginsberg5150 • @iv_Machiavelli • @GRC_Ninja