Cybrary Penetration Tester Syllabus

Last Updated: 08-12-2019

General Information
Welcome! You have officially started your journey in becoming a Penetration Tester. Along the
way you will have the opportunity to connect with real world industry professionals to mentor
you along the way. As you work through the program you will open up highly in-demand job
opportunities; as well as, receive the appropriate knowledge, skills and abilities in order to earn
a new job. In addition, much of the curriculum will provide you the resources to sit for, ​and pass​,
industry recognized certification exams.

Welcome Checklist
1. Choose Career Path relevant to current cybersecurity/IT experience
2. Find your curriculum under “My Career Path” on your home page. (Click on
Cybrary logo to access)
3. Launch into your curriculum and fire up your first assignments (Start at top and
work downward)
4. Need to meet your mentor? You will communicate with them and other Cybrary
Insider Pro members on the community chat application Slack!
5. Visit the “Community” tab and click “Insider Pro Slack” to create an account and
get added to our community!
6. Once you have been added to Slack review the “Greetbot” message for a quick
intro and next steps!

Expectations and Goals

We have found that the students who are most successful in the program spend at least 30
minutes on learning. This includes time for engaging with your mentor and your community.
Communicating difficult concepts is a learned skill and our community provides a risk free for
you to test that skill. In addition our community will show you some of the learnings they have
gotten in the past as they have gone through their journey.

Your time is extremely valuable and so if there is a concept you already know do not hesitate to
skip that portion of the curriculum. This syllabus is meant as a guide for a completely new
person to the field.
The structure for the content is course, lab, assessment. By using the materials concurrently it
will provide you with a surrounding experience that will both enhance your chances of passing
the certification exam and give you the experience you need for the actual job role.

Penetration Testers are highly sought after in the cyber security industry, and this program will
prepare you to confidently apply for this job role and start a new career in cyber security.

Suggested Prerequisites Career Path Completion of one:

● Systems Admin
● Network Engineer
Or
● Network+ and Security+
○ video course and virtual lab

Lead Mentors Names in Slack:

@Mark Nibert

@Shane Markley

Function Provide guidance on:

● Career goals/planning,
● Cybersecurity industry knowledge,
● How to get into a cybersecurity work
role, what a “day in the life” is like,
● Career path content questions,
● All other topics around
cybersecurity/IT

Office Location & Hours EST +7, Manama, Bahrain

EST -3, Las Vegas, Nevada

Certifications You Will Be Prepared For EC-Council CEH

Course Schedule

Penetration Tester

Week Topic Length Format

(Hours)

Step 1 Meet your Mentor by joining 1 Slack Community Chat

Slack Community.

Step 2 Social Engineering 1 Course

Step 3 Kali Linux Fundamentals 1.75 Course

Step 4 Virtual Machine for

Kali Linux Sandbox 1 Practice

Step 5 NMAP 6 Course

Step 6 How to Use hping3 (BSWJ) 0.5 Course

Step 7 How to Use Unicornscan (BSWR) 0.5 Course

Step 8 How to Use Automater (BSWJ) 0.5 Course

Step 9 Malware Analysis 0.5 Course

Step 10 Malware Threats 1 Course

Step 11 Phishing 1.5 Course

Step 12 Phishing 1 Lab

Step 13 Red Team Guide 3 Course

Step 14 USB Drop Attack 2.5 Course

Step 15 Penetration Testing and Ethical

Hacking 10 Course

Step 16 Evasion 0.5 Course

Step 17 Being Stealthy 0.5 Course

Step 18 Pentest Basics: Scanning 0.5 Course

 Networks

Step 19 Network Discovery 1 Lab

Step 20 Open Source Collection 1 Lab

Step 21 Preliminary Scanning 1 Lab

Step 22 Additional Scanning Options 1 Lab

Step 23 Scanning and Mapping Networks 1 Lab

Step 24 Password Cracking 0.5 Course

Step 25 Open Source Password Cracking 1 Lab

Step 26 Use A Password Cracking Utility

in Linux 1 Lab

Step 27 How to Use THC-Hydra (BSWR) 0.5 Course

Step 28 Pentest Basics: Sniffing 0.5 Course

Step 29 Wireshark 1 Lab

Step 30 Use Tcpdump to Intercept

Network Traffic 1 Lab

Step 31 Certified Ethical Hacker (CEH) 20 Lab

Step 32 Identifying System Vulnerabilities

with OpenVAS 1 Lab

Step 33 Vulnerability Scan 1 Assessment

Step 34 Recon 1 Assessment

Step 35 Ethical Hacking Assessment 1 Assessment

Step 36 OWASP Top 10 2017 4.5 Course

Step 37 Web Application Penetration

Testing 4.5 Course

Step 38 Intro to Burp Suite Pro 1 Course

Step 39 SQl Injection 1 Course

Step 40 SQL Injection 1 Lab

Step 41 XSS Reflected 1 Lab

Step 42 XSS Stored 1 Lab

Step 43 Unrestricted File Upload 1 Lab

Step 44 Advanced Penetration Testing 14.5 Course

Step 46 Penetration Tester 1 Assessment

Step 47 Obtain root Credentials in Linux 1 Lab

Step 48 How to Use Armitage - Overview

(BSWJ) 0.25 Course

Step 49 How to Use Armitage - Host

Management (BSWJ) 0.25 Course

Step 50 How to Use Armitage -

Exploitation (BSWJ) 0.25 Course

Step 51 How to Use ExploitDB (BSWJ) 0.25 Course

Use PowerShell to Gather
Step 52 Computer Information in Windows 1 Lab

Step 53 Create a Basic Script using

PowerShell 1 Lab

Step 54 How to Use APT2 (BSWJ) 0.5 Course

Step 55 Intro to Python 3 Course

Step 56 Post Exploitation Hacking 7.75 Course

Step 57 Resume and Job Prep Session 7 Job prep

Cybrary Insider Pro FAQ:

GENERAL

What is the training format of Cybrary?

All of the training through Cybrary is on-demand and available 24/7:
● On-demand Video-Based Courses
● Virtual Hands On Labs
 ● Capture the Flag Assessments
● Monthly Live Webcasts

What is the benefit of Cybrary over other training providers?

Cybrary provides you premium access to innovative, experiential learning and skill
assessment technology. Over 300 tools are available for purchase in the catalog via the
Cybrary Vendor network. The Cybrary platform is an ecosystem, which brings together
the learner and the employer. This partnership allows the individual to develop a deep
understanding of a company, their services or products, and build the skills needed to
advance their career.

Are there any LIVE training courses?

We offer live training courses for certification prep and NICE cybersecurity workforce
education! See the LIVE tab on the Cybrary site for additional information! (Episodes
will be recorded and posted some time after they are recorded for those who were not
able to join in). We primarily use the 24/7 on-demand video-based training format to
provide the flexibility of self-paced learning. This option also allows learners to go back
through any training modules to help them retain information through repetition.

How do I get added to a Career Path channel?

When you chose a Career Path, you will receive a welcome message with instructions
on how to proceed. Please reach out to @Sam from our Customer Success Team for
further assistance.

Which is the best Career Path for me?

Check out the following two links for guiding on choosing a Career Path:
● https://www.cybrary.it/course-paths/
● https://www.cybrary.it/cyber-security-jobs/

CompTIA’s Career Path Roadmap might also help with you decision on how you want
to progress through training. As always, feel free to reach out to any of the Mentors or
Customer Success team for additional guidance.

Can I change Career Paths once I start one?

Of course! We want your learning experience to be exactly what you are looking for. If
you start a career path that you are not comfortable with, just let @Sam from our
Customer Success Team know and they will get you moved over.
How do I access my assignments?
Your assignments are located under your home tab on Cybrary.it under “My
assignments”:

Your assignments are listed from top to bottom base on the syllabus for each career
path. If any of the assignment hyperlinks are broken, please make sure to bring this to
the attention of the Mentors/Customer Success Team so it can be corrected. In the
meantime, you can also search for a specific assignment under the courses catalog -
https://www.cybrary.it/catalog/.

Do I have to follow all of my assignments in the exact order?

The assignments list and syllabus are there for guidance purposes on the best way to
progress through a career path, but they do not need to be followed exactly how they
are listed.

What is the deadline for assignments?

While we provide guidance on how to progress through the various Career Paths, there
are no hard deadlines for assignments. Cybrary’s teaching format is meant to be
self-paced so learners are able to go through the program as slow or as fast as they
chose. We encourage people to use Cybrary as a continuous learning tool as content is
consistently being updated which is very much needed in our ever changing industry.

Will there be any Final Projects?

Yes! We are currently developing this part of the program and we will be releasing
some beta Final Projects for testing.

Is there a mobile version of Cybrary?

Yes! There is a Cybrary.it app currently available for Android. We are still working on
usability testing on this app as well as providing it for different formats.

Who are my mentors?

@Mark Nibert , @Perry and @Shane Markley are the three Senior Mentors for all
Career Paths. There are also a handful of Assistant Mentors assigned to each channel
for additional assistance. Assistant Mentors are also very active in the ​public_chat
channel and will typically have “Assistant Mentor” description in their Slack profile.
@gina is the Mentor to reach out to for job placement assistance, resume building, and
interview skills.
Where can I find additional help with the CTF Exercises?
There is minimal help we can offer with the CTF Exercises/Assessments as those
scores are tracked. We are able to offer general guidance, but not give too much
information on how to answer the questions. If there are any technical issues with the
CTF Exercises or HOLs, please report this to support@practice-labs.com and also
notify your Mentors so they have visibility on the problems that are occurring. If you are
not getting a timely response from the Labs Support Team, please notify @Sam from
our Customer Success Team for escalation assistance.

What is the best certification for me to start with?

We will be doing a more detailed overview for specific certifications in the near future.
Our monthly live webinars also go into detail for certifications based on the specific
Career Path that is being covered. CompTIA’s IT Certification Roadmap is also a great
resource.

How do I become an Assistant Mentor?

Mentoring gives you the extraordinary opportunity to facilitate a protege's personal and
professional growth by sharing knowledge you learned through your experience. While
the primary intent of your mentoring role is to challenge the protege to think in new and
different ways, the protege is not the only one who gains from the arrangement. As a
mentor, there are various ways you can benefit as well:
• Enhance your skills. The experience you gain by mentoring someone can
facilitate your own professional growth, making you more of an asset to your
organization/industry. Mentoring allows you to strengthen your coaching and leadership
skills by working with individuals from different backgrounds and with different
personality types.
• Develop and retain talent in your organization. Your role as a mentor can
contribute to the success of your entire organization. As a Cybersecurity professional,
you know the importance of developing and retaining good employees.
• Create a legacy. By becoming a mentor, you create a legacy that has a
lasting impact on your protege and the Cybersecurity field.
• Opportunity to be promoted to a Junior Mentor for future cohorts.

Reach out to @Mark Nibert, @Shane Markley and @Perry for additional information.

Can I “test out” of any of my assignments?

If you have direct work experience or hold a current certification in a subject you may
skip the content and move to the next subject. The purpose of the career path is to
ensure you have all the Knowledge/skills/abilities associated with the program. If you
already have them there is no need to duplicate efforts.

Will any of the Career Paths prepare me to take any certifications?

Each career path has certification courses, these courses will prepare you to take the
certification it is teaching. If you feel like you need more training or other resources
please reach out to the mentors to get supplemental material. This material may be on
Cybrary but they can also make recommendations on things to use outside of Cybrary
to help you obtain that certification.

I am having trouble with <insert lab, course, assessment, CTF>? How do I find
help?
Our first recommendation is to post any questions you have in the cohort channel. If no
one responds you can also try the public chat. The assistant mentors and career
mentors are also here to help if those options do not work. Please remember that
investigation and research is a large part of the learning process and only becomes
more prominent as you move forward in your career.

TECHNICAL ISSUES

How do I troubleshoot general access issues with Labs?

First, always clear cache, cookies and allow all pop-ups.​ If it is a potential
access issue or glitch with the lab, it might be a good idea to restart the individual VMs
or log out and back into the lab environment. If you are able to recreate the issue in the
lab, then the problem might be with the actual lab itself and the issue should be
submitted. They can be contacted via the Help and Support tab within the labs or by
emailing support@practice-labs.com. It is always a good idea to post something to
your channel to see if anyone else is experiencing any issues and so that the Mentors
and Customer Success staff have knowledge that this is occurring. There is usually a
way to find a workaround, but if not, feel free to skip over that particular exercise and
continue forward for now so they do not get too far behind.

How do I troubleshoot issues with VMs not starting?

It is a good idea to try logging out and back into the lab environment to see if the issue
still exists. It is also a good idea to test from a different OS or computer if this option is
available. This will help to further troubleshoot the issue.

What do I do if I have issues with the CTF Assignments?

There is minimal help we can offer with the CTF Exercises/Assessments as those
scores are tracked. We are able to offer general guidance, but not give too much
information on how to answer the questions.

ADMINISTRATIVE QUESTIONS
Whom do I contact in regards to Accounting/Billing questions?
The Cybrary Customer Success Team can assist you with any questions regarding
billing/account in the chat icon on the Cybrary.it website. We have access to your
account information here so the process is as quick and seamless as possible.

Whom do I provide general feedback to?

Feedback is always encouraged and appreciated. The Cybrary Team logs all feedback
through the chat icon on your Cybrary.it website.

JOB PLACEMENT
Hiring managers are looking for cyber experience and I don’t have any. What
should I do?
This is an age-old issue that many new and transitioning job seekers face. We
encourage you to keep persisting in seeking experience. Everyone starts somewhere
and, odds are, someone will give you your “big break” at some point.
Additionally, here are a few ways to potentially acquire non-traditional experience: take
part in free hackathons and CTFs; join a Meetup that focuses on IT and Cyber issues
(although this won’t provide experience, it will show industry involvement and may be a
good place to network); consider doing volunteer work in your area of interest (if you
can afford to do so).

How do I add my Cybrary courses/career path to my resume?

We often recommend adding your courses/career path to the “Education” section on
your resume. Keep in mind that if you’ve not yet completed your courses or career path,
you might write something like this:

Does my resume need to be one page?

The short answer: No. Why? These days, job seekers (especially cyber and IT) have
many skills, certs, accomplishments, educational components, and experience they
should include on their resume; this info does not often fit on one page. Also, remember
that your resume may be loaded into a database, in which case the number of pages is
not relevant. Be aware, though, that you should aim to keep the MS Word version of
resume to three pages max.

How can I improve my interview skills?

Reading, researching, and practice can all help. Read articles (and watch free videos)
on how to be a better interviewee. Research the companies with whom you have
interviews. Learn everything you can about them. Practice interviewing with a friend or
the career mentor at Cybrary (via Skype).