External Pentest Playbook

Learn to conduct an external network penetration test from start to finish.

Training for a team or organization? Contact us about group access.

External pentest playbook course logo

Inside the Course

Scroll down to explore the skills you’ll build, the techniques you’ll master, and the requirements to get started.

Start Learning This Course Today

The All-Access Membership gives you unlimited access to this course, hands-on labs, and a complete library of cybersecurity training. Everything you need to build real-world skills is included.

Questions?

If you need clarification on the course or its requirements, simply use the chat button below and our team will assist you.

  • Difficulty: Beginner
  • Duration: 3h 30m
  • Access: Included in Membership

Overview

This course focuses on external penetration testing tactics and techniques designed to help you improve your pentest game. Students should take this course if they are interested in the following topics:

 

  • Objectives of an External Pentest
  • Important Documents and Procedures
  • Scope Verification and Client Communication
  • Attack Strategies
  • Vulnerability Scanning
  • Common OSINT and Information Gathering Techniques
  • Attacking O365/OWA and Login Portals
  • Bypassing MFA and Escalating Access
  • Report Writing
  • Identifying Common Pentest Findings
  • Client Debriefs, Retests, and Attestations

Live Training Available for This Topic

Looking to go deeper? This course aligns with upcoming instructor-led sessions covering real-world applications and guided labs.

Objectives

Build an External Pentest Attack Methodology:

  • Gain a better understanding of the external pentest attack methodology and mindset.

Become a Better Penetration Tester:

  • Improve overall penetration testing skillset and client relations.

Get Hired:

  • Crush their next penetration testing job interview.

System Requirements

Students need a PC that runs Windows, Mac OSX, or Linux. No specific memory or space requirements exist for this course.

Prerequisites

  • Previous beginner pentest knowledge strongly preferred
  • Prior basic security knowledge strongly preferred

Course Curriculum

  • Introduction
    • Introduction
    • Course Discord
  • Before We Start
    • Objectives of an External Pentest
    • Checklists, FTW
    • Rules of Engagement
    • Verifying Scope
    • Client Communication
  • Kicking Off
    • Attack Strategy
    • Vulnerability Scanning
    • Reviewing & Extracting Information
  • Information Gathering / OSINT
    • Overview
    • Hunting Breached Credentials
    • Identifying Employees & Emails
    • Enumerating Valid Accounts (Pre-Attack)
    • Other Useful Information
  • Attacking Login Portals
    • Overview & Strategy
    • Attacking O365
    • Attacking OWA
    • Attacking Other Portals
    • Bypassing MFA
  • Escalating Access
    • Strategy & Walkthrough
  • Report Writing
    • Report Writing
  • Common Pentest Findings
    • Overview
    • Insufficient Authentication Controls
    • Weak Password Policy
    • Insufficient Patching
    • Default Credentials
    • Insufficient Encryption
    • Information Disclosure
    • Username Enumeration
    • Default Web Pages
    • Open Mail Relays
    • IKE Aggressive Mode
    • Unexpected Perimeter Services
    • Insufficient Traffic Blocking
    • Undetected Malicious Activity
    • Historical Account Compromises
  • Wrapping Up
    • Client Debriefs
    • Attestation Letters
    • Client Retests
    • Next Steps: The Practical Network Penetration Tester (PNPT) Certification
  • Conclusion
    • Course Conclusion

This Course Is Included in Your All-Access Membership

One membership gives you ongoing access to External Pentest Playbook, every other paid Academy course, and an active community of learners and mentors in Discord.

INSTRUCTORS

Meet Your Instructor

Learn from industry experts with real-world cybersecurity experience.

Instructor Heath Adams

Heath Adams

Hi everyone! My name is Heath Adams, but I also go by “The Cyber Mentor” on social media. I am the founder and CEO of TCM Security, an ethical hacking and cybersecurity consulting company. While I am an ethical hacker by trade, I love to teach! I have taught courses to over 170,000 students on multiple platforms, including Udemy, YouTube, Twitch, and INE.

I am currently OSCP, OSWP, eCPPTX, eWPT, CEH, Pentest+, CCNA, Linux+, Security+, Network+, and A+ certified.

I’m also a husband, animal dad, tinkerer, and military veteran. I hope you enjoy my courses.

FAQS

Common Questions

Here are a couple of our most commonly asked questions, contact us if you don’t find an answer!

Can I get a refund if I'm unhappy with my purchase?
2
3

Yes. All courses come with a 24-hour money-back guarantee.

Will I receive a certificate of completion when I finish a course?
2
3

Yes. All courses come with a certificate of completion.

Do the courses count as Continuing Education Units (CEUs)?
2
3

Yes. Every certificate of completion comes with the total CEUs earned listed on the certificate.

What is the All-Access Membership?
2
3

As of July 1st, 2023 TCM Academy transitioned to a monthly subscription model, where you now receive full access to all of the courses on our platform for as long as your subscription remains active.

What if you already own courses on TCM Academy?
2
3

If you already own a course on our platform, you will continue to own that course. Previously owned courses will not be affected by this change.

I can see the course, but it won’t load or play. What should I do?
2
3

We use Cloudflare to protect our course platform and unfortunately, it does not play nice with VPNs. If you are experiencing issues, turn off your VPN and try again. If that does not solve the issue, please contact our support team at support@tcm-sec.com and we will help you out.

This course is included in our All-Access Membership, starting at $29.99/month.

Get full access to this course and our full course catalog when you enroll in our All-Access Membership.

Ready to level up your Cybersecurity Career?

Get unlimited access to every TCM Security Academy course, hands-on lab, and certification pathway with an All-Access Membership. Learn at your own pace, build real-world skills, and take the next step toward a career in cybersecurity.

PWPA