Re: Penetration Testing

[Velislav K Pavlov <VelislavPavlov () FERRIS EDU>]

There may not be a one-size fits all solution. Perform gaps analysis between your needs and what you have in place:

·        Why are you doing this? Good stewardship? Make sure to also review your data classification and compliance 
requirements (HIPAA, PCI DSS, FERPA, etc.).

·        Where is the data?

o    Identify your scope. We employ sampling approach for the sake of time and resource utilization.

o   All devices configured the same way are likely to have the same vulnerabilities. We learned that through PCI DSS 
assessments.

o   Identify your attack surface: externally vs internally visible assets, services/ports. Do all of your assets 
(ports/services) need to be publically visible? The smaller the surface, the less we will have to assess, remediate, 
and defend. We started with outside-in approach (blackbox) then inside-out (grey/white) until we reached the maturity 
of holistic approach that covers both.

o   Are you testing the people, processes, and/or technology?

·        How are you doing the assessment?

o   Identify the type of your assessment. There are differences between risk assessment/audit, vulnerability 
assessment, and pen test.

o   My go to guideline for pen test is PTES http://www.pentest-standard.org/index.php/Main_Page

o   What tools will you use? We use commercial and open source products. Pick a tool or two (primary and secondary) 
that do the job reliably and accurately. Become proficient with them. Automate as much as you can, but always verify 
the results for accuracy. We use a tool to automate the finding of low hanging fruits on all of our assets. We then use 
complimentary tools to pick the low-hanging fruits and probe further as needed.

o   How are you tracking the remediation progress? Creating a simple spreadsheet, risk register, with identified 
vulnerabilities (including service, port, etc), severity, team assignments, remediation recommendation, and remediation 
progress can go a long way. Sometimes you can use your commercial vulnerability lifecycle management tool to create 
tickets and track risk lifecycle. Record the results as they become available. Don’t wait until you have to write a 
report. We moved away from writing long reports. Executive summary with risk register, spreadsheet format, that can 
easily filtered, sorted, and graphed may be just enough reporting to get the job done.

·        What are the end-goals/objectives? Everyone and everything is vulnerable and can be eventually exploitable. 
What are you trying to prove? The assessment should not be used to point fingers at other people and departments.

o   Prove that a known vulnerability exists?

o   Prove that zero-day vulnerability exists?

o   Prove that exploit exists?

o   Prove that systems uses default credentials or configuration?

o   Determine your preparedness to detect and react to threats and vulnerabilities?

o   Address compliance requirements?

o   Pivot to ERP, file servers, DA, servers with PCI, HIPAA data?

o   Improve/validate your security posture?

·        When are you going to do it?

o   Timing is everything. We found out that we have to navigate the academic calendar along with the calendar and 
priorities of the IT operations so we can work on timely remediation. Finding the problems is just part of the 
equation. Remediating takes the most time and effort. Consider also when you are doing the assessments what day of the 
week and time of the day you are doing them. Resource intensive assessments can cause performance degradation.

·        Who is trained or will be trained to do the assessment?

o   If the scope is PCI, there are some requirements for the internal staff; review the PCI DSS Pen Testing Guidelines 
https://www.pcisecuritystandards.org/documents/Penetration_Testing_Guidance_March_2015.pdf


We started with risk assessment based on HIPAA and PCI DSS, then converted to ISO27001/27002 as it translates to any 
major risk framework and regulation. We created vulnerability lifecycle management program where all ITS managed assets 
are scanned weekly. Assets are broken down by support admin, each with their own visualization dashboard. The cycle 
helps to address vulnerabilities and track changes before and after maintenance. We eventually matured to validating 
the known vulnerabilities during each weekly scan. Remediation is the biggest hurdle. What helps us is standardization 
on prioritization and timelines for remediation driven by CVSS overall severity score, risk classification, 
vulnerability age, data classification, remote code execution vs local, availability of exploit, available fix, attack 
surface/visibility, availability of compensating controls, etc. We still do at least yearly vendor delivered pentest. 
This is done to validate our internal efforts and address compliance and data handling requirements. I find that purple 
team engagement where you look over the pentesters can help train the internal staff or at least validate their 
practices. The more you scan, the more you can fix and address. Eventually, the assessments becomes standard 
operational procedure and it becomes easier to spot deviations from the known standard. If you are interested in 
discussion about tools and specific techniques, my email is provided below. Take care.


Vel Pavlov | Coordinator, IT Security
M.Sc. ISM, CISSP, C|HFI, C|EH, C)PTE,
Security+, CNA, MPCS, ITILv3F, A+
VelPavlov () ferris edu<mailto:VelPavlov () ferris edu>

From: The EDUCAUSE Security Constituent Group Listserv [mailto:SECURITY () LISTSERV EDUCAUSE EDU] On Behalf Of Barton, 
Robert W.
Sent: Wednesday, May 31, 2017 12:46 PM
To: SECURITY () LISTSERV EDUCAUSE EDU
Subject: Re: [SECURITY] Penetration Testing

**Notice** This message is from a sender outside of the Ferris Office 365 mail system. Use caution when clicking links 
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We have done a POC here (I was not the professor).  The students were asked to “look around”, and try to think like a 
hacker as part of individual class projects.  The best three did find some interesting things, but I would say there 
focus would need to be refined to make it a better project, make it a team project, and the time given needs to 
increase (e.g. what is a good item to attack; the wireless network you found, or the web site, based on 
time/resources?).  Maybe too much freedom for somebody beginning this type of discovery…?  Send me an email privately 
if you want to talk more about it.

The Bradley course did a large scale attack; enumeration through social engineering.  It was a full semester long.

Robert W. Barton
Director of Information Security
Lewis University
One University Parkway
Romeoville, IL  60446-2200
815-836-5663

From: The EDUCAUSE Security Constituent Group Listserv [mailto:SECURITY () LISTSERV EDUCAUSE EDU] On Behalf Of Mike 
Cunningham
Sent: Wednesday, May 31, 2017 11:35 AM
To: SECURITY () LISTSERV EDUCAUSE EDU<mailto:SECURITY () LISTSERV EDUCAUSE EDU>
Subject: Re: [SECURITY] Penetration Testing

Have you ever had your own students do a penetration test against the University systems?  Both inside and out?


Mike Cunningham
VP of Information Technology Services/CIO
Pennsylvania College of Technology



From: The EDUCAUSE Security Constituent Group Listserv [mailto:SECURITY () LISTSERV EDUCAUSE EDU] On Behalf Of Barton, 
Robert W.
Sent: Wednesday, May 31, 2017 12:18 PM
To: SECURITY () LISTSERV EDUCAUSE EDU<mailto:SECURITY () LISTSERV EDUCAUSE EDU>
Subject: Re: [SECURITY] Penetration Testing

Bradley University has a class on penetration testing; they did a “red team” attack against an outside company.  The 
idea was to do outside and inside the following year (they had to get people on-board).  They did a presentation at 
ForenSecure this year.

Robert W. Barton
Director of Information Security
Lewis University
One University Parkway
Romeoville, IL  60446-2200
815-836-5663

From: The EDUCAUSE Security Constituent Group Listserv [mailto:SECURITY () LISTSERV EDUCAUSE EDU] On Behalf Of David 
Santos
Sent: Wednesday, May 31, 2017 11:03 AM
To: SECURITY () LISTSERV EDUCAUSE EDU<mailto:SECURITY () LISTSERV EDUCAUSE EDU>
Subject: [SECURITY] Penetration Testing

Hi All,

We do one every couple years by an outside vendor but we would like to start doing more on our own; possibly every 6 
months.  So, I’m looking for any penetration testing plans or the process used for conducting pen testing on your own. 
Any thoughts or ideas welcomed, thanks again.

Looking forward to your responses.

Have a Great Day!

David Santos
IT Security & Helpdesk Manager,
Information Technology

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Felician University
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