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CYBERSECURITY IN THE DIGITAL ERA WEBCAST SERIES
“HACK YOURSELF FIRST: HANDS ON ETHICAL HACKING”
SPEAKERS:WEBINAR HOST:
Ana Curreya
Marketing Director
DigitalEra Group
Ricardo Martinez
Director of Business
Development
DigitalEra Group
Jorge Orchilles
Professional Hacker
SANS
Thank you for joining our webinar today. We will begin shortly.
www.DigitalEraGroup.com ∣ (786) 621-8600 ∣
GUEST SPEAKER
Jorge Orchilles
Professional Hacker
SANS
@jorgeorchilles
• Led the offensive security team at large financial – 10 years!
• Published author with industry contributions including:
• Common Vulnerability Scoring System (CVSSv3.1)
• Threat-led penetration testing framework (GFMA)
• SANS Certified Instructor
• Author of SEC564: Red Team Exercises and Adversary Emulation
• NSI Technologist Fellow
• ISSA fellow
• Board of the ISSA South Florida since 2010
• Author of Windows 7 Administrators Reference
ABOUT @JorgeOrchilles
@jorgeorchilles
• A hacker is a skilled individual who uses their technical knowledge to
overcome a problem
• Permission differentiates between ethical and sinister, often called
White Hat and Black Hat respectively
• An Ethical Hacker is a person who hacks into a computer network in
order to test or evaluate its security, rather than with malicious or
criminal intent
https://medium.com/@jorgeorchilles/ethical-hacking-definitions-
9b9a6dad4988
Ethical Hacking
@jorgeorchilles
• Definition: Automated (tool-based) scanning against assets (IPs or -
applications)
• Goal: Identify low hanging, known vulnerabilities pre, or post-
authentication
• Effort: Small; requires tool investment
• Many vendors: Tenable Nessus, Rapid7 Nexpose, Qualys, AlientVault,
IBM AppScan, HP WebInspect, etc.
• Focus: Technology vulnerabilities, patches, configuration
• Frequency: Weekly to Monthly
• Customer: System owners and operations teams
Vulnerability Scanning
@jorgeorchilles
Vulnerability Scanning
Demo
@jorgeorchilles
• Definition: Automated and manual assessment of assets in scope to
find security vulnerabilities, which may or may not be used to get in or
steal data
• Goal: Identify ALL vulnerabilities from assets in scope
• Effort: ~30% tools based and ~70% manual testing
• Focus: Technology and Configurations. Assessments are broader and
often include explicit policy and procedure reviews
• Frequency: Once per year or once per certification of product/version
• Customer: System owners, operations, engineers, application
stakeholders
Vulnerability Assessments
@jorgeorchilles
Vulnerability Assessment
Demo
@jorgeorchilles
• Definition: exploit the vulnerabilities identified; in a professional, safe
manner according to a carefully designed scope and Rules of
Engagement; to determine business risk and potential impact
• Goal: Report all exploitable vulnerabilities under controlled
circumstances.
• Effort: ~10% tools based and ~90% manual testing
• Focus: technology and preventive controls
• Frequency: ~once per year
• Customer: System owners, operations, engineering, and application
stakeholders
PenetrationTesting
@jorgeorchilles
Exploitation Demo
@jorgeorchilles
• Common Vulnerability Scoring System (CVSS)
• Exploit Predictability Scoring System (EPSS)
• AttackerKB.com
• Tenable Vulnerability Priority Rating
• Rapid7 Real Risk Score
• Mandiant/FireEye Risk Rating
https://medium.com/@jorgeorchilles/vulnerability-management-is-hard-
how-do-you-prioritize-what-to-patch-1fc8e163d740
Prioritization is Hard!
@jorgeorchilles
• Common Vulnerabilities and Exposures (CVE)
• https://cve.mitre.org
• Tactics, Techniques, and Procedures (TTPs)
• https://attack.mitre.org
• Assume Breach
• You will get breached by an exploited vulnerability or a TTP
“I am convinced that there are only two types of companies: those that have been
hacked and those that will be.” – Robert Muller March 1, 2012 RSA
• Can you detect and respond to what comes after?
Evolve from CVE toTTP
@jorgeorchilles
• Definition: Red Team emulates Tactics, Techniques, and Procedures (TTPs) of
real adversaries to improve the people, processes, and technology in the
target environment. “The practice of looking at a problem or situation from
the perspective of an adversary” – Red Team Journal 1997
• Goal: Make Blue Team better. Train and measure blue teams' detection and
response policies, procedures, and technologies are effective.
• Effort: Manual; some Red Team Automation tools
• Focus: detective controls; testing the defenders
• Frequency: Intelligence-led (new exploit, tool, or TTP)
• Customer: Blue Teams
RedTeam
@jorgeorchilles
• Definition: the defenders in an organization entrusted with identifying
and remediating attacks. Generally associated with Security Operations
Center or Managed Security Service Provider (MSSP), Hunt Team,
Incident Response, and Digital Forensics. Really, it is everyone's
responsibility!
• Goal: identify, report the attack, contain, and eradicate attacks
• Effort: Automated and Manual. People are the best defenders
• Focus: identify, contain, eradicate, and recover from attacks
• Frequency: Every Day 24/7
• Customer: entire organization
BlueTeam
@jorgeorchilles
• Definition: A function, or virtual team, where red and blue work
together to improve the overall security of the organization. Red Team
does not focus on stealth as they normally would.
• Goal: Red Team emulates adversary TTPs while blue teams watch and
improve detection and response policies, procedures, and technologies
in real time.
• Effort: Manual
• Frequency: Intelligence-led (new exploit, tool, or TTP)
• Customer: Red Team & Blue Team
PurpleTeam
@jorgeorchilles
• Definition: A type of Red Team exercise where the Red Team emulates
how an adversary operates, following the same tactics, techniques, and
procedures (TTPs), with a specific objective similar to those of realistic
threats or adversaries.
• Goal: Emulate an end-to-end attack against a target organization.
Obtain a holistic view of the organization’s preparedness for a real,
sophisticated attack.
• Effort: Manual; more setup than a limited scope Penetration Test
• Frequency: Twice a year or yearly
• Customer: Entire organization
Adversary Emulation
@jorgeorchilles
EmulatingTTP Demo
• All these ethical hacking and offensive security offerings are meant to
provide value to the business (getting a shell is not business value)
• Understand the business requirements and communicate in business
terms
DigitalEra has partnered with AvanseCyber, where I am an advisor, to
deliver these services, contact us if you are interested in learning more or
if you would like an assessment
Provide Value
www.DigitalEraGroup.com ∣ (786) 621-8600 ∣ info@avansecyber.com
Provide Value
www.DigitalEraGroup.com ∣ (786) 621-8600 ∣ info@avansecyber.com
www.DigitalEraGroup.com ∣ (786) 621-8600 ∣
Q&A
www.DigitalEraGroup.com ∣ (786) 621-8600 ∣
THANKYOU

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Ethical Hacking Definitions Matter - Covering Vulnerability Scanning, Vulnerability Assessment, Penetration Testing, Red Team, Blue Team, Purple Team, and Adversary Emulation

  • 1. CYBERSECURITY IN THE DIGITAL ERA WEBCAST SERIES “HACK YOURSELF FIRST: HANDS ON ETHICAL HACKING” SPEAKERS:WEBINAR HOST: Ana Curreya Marketing Director DigitalEra Group Ricardo Martinez Director of Business Development DigitalEra Group Jorge Orchilles Professional Hacker SANS Thank you for joining our webinar today. We will begin shortly.
  • 2. www.DigitalEraGroup.com ∣ (786) 621-8600 ∣ GUEST SPEAKER Jorge Orchilles Professional Hacker SANS
  • 3. @jorgeorchilles • Led the offensive security team at large financial – 10 years! • Published author with industry contributions including: • Common Vulnerability Scoring System (CVSSv3.1) • Threat-led penetration testing framework (GFMA) • SANS Certified Instructor • Author of SEC564: Red Team Exercises and Adversary Emulation • NSI Technologist Fellow • ISSA fellow • Board of the ISSA South Florida since 2010 • Author of Windows 7 Administrators Reference ABOUT @JorgeOrchilles
  • 4. @jorgeorchilles • A hacker is a skilled individual who uses their technical knowledge to overcome a problem • Permission differentiates between ethical and sinister, often called White Hat and Black Hat respectively • An Ethical Hacker is a person who hacks into a computer network in order to test or evaluate its security, rather than with malicious or criminal intent https://medium.com/@jorgeorchilles/ethical-hacking-definitions- 9b9a6dad4988 Ethical Hacking
  • 5. @jorgeorchilles • Definition: Automated (tool-based) scanning against assets (IPs or - applications) • Goal: Identify low hanging, known vulnerabilities pre, or post- authentication • Effort: Small; requires tool investment • Many vendors: Tenable Nessus, Rapid7 Nexpose, Qualys, AlientVault, IBM AppScan, HP WebInspect, etc. • Focus: Technology vulnerabilities, patches, configuration • Frequency: Weekly to Monthly • Customer: System owners and operations teams Vulnerability Scanning
  • 7. @jorgeorchilles • Definition: Automated and manual assessment of assets in scope to find security vulnerabilities, which may or may not be used to get in or steal data • Goal: Identify ALL vulnerabilities from assets in scope • Effort: ~30% tools based and ~70% manual testing • Focus: Technology and Configurations. Assessments are broader and often include explicit policy and procedure reviews • Frequency: Once per year or once per certification of product/version • Customer: System owners, operations, engineers, application stakeholders Vulnerability Assessments
  • 9. @jorgeorchilles • Definition: exploit the vulnerabilities identified; in a professional, safe manner according to a carefully designed scope and Rules of Engagement; to determine business risk and potential impact • Goal: Report all exploitable vulnerabilities under controlled circumstances. • Effort: ~10% tools based and ~90% manual testing • Focus: technology and preventive controls • Frequency: ~once per year • Customer: System owners, operations, engineering, and application stakeholders PenetrationTesting
  • 11. @jorgeorchilles • Common Vulnerability Scoring System (CVSS) • Exploit Predictability Scoring System (EPSS) • AttackerKB.com • Tenable Vulnerability Priority Rating • Rapid7 Real Risk Score • Mandiant/FireEye Risk Rating https://medium.com/@jorgeorchilles/vulnerability-management-is-hard- how-do-you-prioritize-what-to-patch-1fc8e163d740 Prioritization is Hard!
  • 12. @jorgeorchilles • Common Vulnerabilities and Exposures (CVE) • https://cve.mitre.org • Tactics, Techniques, and Procedures (TTPs) • https://attack.mitre.org • Assume Breach • You will get breached by an exploited vulnerability or a TTP “I am convinced that there are only two types of companies: those that have been hacked and those that will be.” – Robert Muller March 1, 2012 RSA • Can you detect and respond to what comes after? Evolve from CVE toTTP
  • 13. @jorgeorchilles • Definition: Red Team emulates Tactics, Techniques, and Procedures (TTPs) of real adversaries to improve the people, processes, and technology in the target environment. “The practice of looking at a problem or situation from the perspective of an adversary” – Red Team Journal 1997 • Goal: Make Blue Team better. Train and measure blue teams' detection and response policies, procedures, and technologies are effective. • Effort: Manual; some Red Team Automation tools • Focus: detective controls; testing the defenders • Frequency: Intelligence-led (new exploit, tool, or TTP) • Customer: Blue Teams RedTeam
  • 14. @jorgeorchilles • Definition: the defenders in an organization entrusted with identifying and remediating attacks. Generally associated with Security Operations Center or Managed Security Service Provider (MSSP), Hunt Team, Incident Response, and Digital Forensics. Really, it is everyone's responsibility! • Goal: identify, report the attack, contain, and eradicate attacks • Effort: Automated and Manual. People are the best defenders • Focus: identify, contain, eradicate, and recover from attacks • Frequency: Every Day 24/7 • Customer: entire organization BlueTeam
  • 15. @jorgeorchilles • Definition: A function, or virtual team, where red and blue work together to improve the overall security of the organization. Red Team does not focus on stealth as they normally would. • Goal: Red Team emulates adversary TTPs while blue teams watch and improve detection and response policies, procedures, and technologies in real time. • Effort: Manual • Frequency: Intelligence-led (new exploit, tool, or TTP) • Customer: Red Team & Blue Team PurpleTeam
  • 16. @jorgeorchilles • Definition: A type of Red Team exercise where the Red Team emulates how an adversary operates, following the same tactics, techniques, and procedures (TTPs), with a specific objective similar to those of realistic threats or adversaries. • Goal: Emulate an end-to-end attack against a target organization. Obtain a holistic view of the organization’s preparedness for a real, sophisticated attack. • Effort: Manual; more setup than a limited scope Penetration Test • Frequency: Twice a year or yearly • Customer: Entire organization Adversary Emulation
  • 18. • All these ethical hacking and offensive security offerings are meant to provide value to the business (getting a shell is not business value) • Understand the business requirements and communicate in business terms DigitalEra has partnered with AvanseCyber, where I am an advisor, to deliver these services, contact us if you are interested in learning more or if you would like an assessment Provide Value www.DigitalEraGroup.com ∣ (786) 621-8600 ∣ info@avansecyber.com
  • 19. Provide Value www.DigitalEraGroup.com ∣ (786) 621-8600 ∣ info@avansecyber.com
  • 21. www.DigitalEraGroup.com ∣ (786) 621-8600 ∣ THANKYOU

Editor's Notes

  1. Introduce our Webinar Series Every Thursday Weekly Guest Speakers from Industry Leading Vendors Incentives for participating in each webinar, as well as incentives for participating in consecutive webinars One-on-one calls scheduled after each webinar where needed
  2. Reference: https://medium.com/@jorgeorchilles/ethical-hacking-definitions-9b9a6dad4988 More reading: https://github.com/redteamethics/redteamethics Petition: https://www.change.org/p/organizations-support-ethical-hackers
  3. Reference: https://archives.fbi.gov/archives/news/speeches/combating-threats-in-the-cyber-world-outsmarting-terrorists-hackers-and-spies