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Penetration Testing
Matthew O’Donnell
&
Sam Eaton-Rosen
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General goals of pentest
- increase sophistication required of
attacker
- quantify risk
- cyber roadmap
2
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General goals of pentest
3
Goals of a
given penetration test
- test defences or build defence
- trophy or coverage-driven
- post-engagement steps
- increase sophistication required of
attacker
- quantify risk
- cyber roadmap
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What pentesters do
4
- stay current on infosec
- simulate threat actors
- listen & communicate
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- stay current on infosec
- simulate threat actors
- listen & communicate
Simulated threat actors
- casual cybercriminal (CCC)
- advanced persistent threat groups
(APT)
- cyber-curious student (CCS)
What pentesters do
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Tiers & targets of pentest
- (un)credentialed
- maximum/minimum exploitation
- end-users
- applications
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Credentialed
7
- remote desktop
- breach simulation
- data sensitivity
- builds defences
- advanced threat simulation
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Credentialed
8
Uncredentialed
- casual cybercrime simulation
- tests defences
- vantage from Google & IP range
- Bring Your Own Device
- remote desktop
- breach simulation
- data sensitivity
- builds defences
- advanced threat simulation
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Whitelisted
9
- maximum coverage
- automation-friendly
- builds defences
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- maximum coverage
- automation-friendly
- builds defences
Blacklisted
- entirely manual
- time/coverage compromise
- tests defences
Whitelisted
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Maximum exploitation
11
- non-disruptive & non-destructive
- identify, confirm, exploit
- lateral movement
- tests defences
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Maximum exploitation
12
Minimum exploitation
- collaborative
- identify, notify, fix
- rapid remediation
- builds defences
- non-disruptive & non-destructive
- identify, confirm, exploit
- lateral movement
- tests defences
Insert footer 13
- social engineering
- spearphishing
- physical infiltration
- users are the perimeter
End-users
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End-users
14
- social engineering
- spearphishing
- physical infiltration
- users are the perimeter
Spearphishing
- levels of sophistication
- credential harvesting
- tests users & vendors
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Application
- commercial HR/finance
- in-house & SDLC
- ADFS & trust
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Reporting
16
- discoverability
- exploitability
- impact
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Reporting
17
- discoverability
- exploitability
- impact
Q & A ?

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