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Vlad Styran
Next Generation Pentest
  Your Company Cannot Buy
why both consultants and customers
          are doing it
             wrong
Who’s that guy?
•   Security Consultant for BMS Consulting
•   Social Engineering researcher
•   InfoSec blogger
•   Podcaster
Why he is here?
• Pentesting since 2006
  – Web sites, banking systems, telecom,
• X commercial pre-sale presentations
  – Saw client’s eyes BEFORE the test
• X-Y pentest reports written
  – Saw client’s eyes AFTER the test
  – Writing reports is HELL
• Z pentest reports read
  – Reading others’ reports is FUN
• CISSP, CEH, CISA…
  – Because it rarely matters
Why are YOU here?
• This preso is for those who want a great
  pentest to be done
    – and someone to benefit from this pentest
       • usually it’s a company
•   You may be a customer
•   Or a consultant
•   Or both
•   And you should agree that there’s something
    wrong with pentesting industry
Some definitions
•   What is a Penetration Test?
•   What is a Vulnerability Assessment?
•   What is the difference?
•   Why should anyone bother?


               • And let’s make it quick and simple
Test
• Testing is deeply interactive
• A test is something a tester and what is tested
  do both
  – We act and see the reaction
  – Not just look, measure and record
  – We touch, push and kick
  – We challenge what we test
• Test has a goal
Penetration Test
• Penetration is getting through obstacles:
   – Security systems
   – User awareness
   – Physical barriers
• The pentest succeeds if we get through
   – And fails if we don’t
        • And this usually means right the opposite to client
• The goal is virtually anything, but
   –   Penetrate a system
   –   Pwnz0r everything: DBA, root, Domain Admin
   –   ‘Get’ the data to show it’s vulnerable
   –   Show that the business might be stopped
Vulnerability Assessment
• Find all vulnerabilities
   – Remove false positives (optional)
• And tell us how to fix them
   – Usually in couple of deferent ways
• Don’t try to break anything, it might… break!
• Come in few weeks (months?) and check how
  whether we fixed stuff
The Difference
• Deep interactivity:
   – Pentest is interactive to the very deep you can get
   – Vulnerability Assessment is superficial
• The goal:
   – Pentest aims at a narrow goal
   – Vuln Assessment is as broad as client can pay for
• The PenTest is focused and thorough
• The VA is a mile broad and a feet deep
• You can easily do VA yourself but PT isn’t easy
   – Not because it’s hard to do, because of conflict of interest
More Difference
• PT not just scans, it exploits
• Most pentest standards do multiple channels
  – Systems and network
  – Wireless and telecom
  – Human interaction
  – Physical stuff
• VA is purely technical
  – Systems and network
  – And maybe wireless… or telecom…
That was ‘what’ and ‘how’.
           What about ‘why’?
• And this is the most important and interesting
  part that everyone should know
• Vulnerability Assessment:
  “Let us know how we can fix what is presumably
  already broken”
• Penetration Test:
  “Try to break what is presumably unbreakable”*

   *Considering reasonable time and resources available
Now To Work
•   Why clients buy pentests?
•   How consultants do pentests?
•   Why clients get bad pentests?
•   What can we do to fix it?
    – Clients
    – Pentesters
How consultants do pentests?
• We set the scope
  – Systems, locations, people, contacts etc.
• We do recon
  – Short for ‘reconnaissance’
• We enumerate the targets
  – And search for vulnerabilities
• It is pretty much the VA until this point
How consultants do good pentests?
• We validate the vulnerabilities
  – ‘Validate’ stand for ‘exploit’ since business people
    don’t like hacker jargon
• We leverage access gained and pivot further
  – Into the network, into the sun, into the cookies…
• We collect evidence of your data compromise
  – Without actually compromising the data
  – But enough to make your bosses like OMG
How consultants do outstanding
            Pentest-NG?
• We meet your business people beforehand
  – To know how your business lives
  – And research on how someone can kill it
• We do all channels and vectors
  – We plan for HR interviews and local conferences
  – We write custom software and exploit code
• We do virtually anything to make you cry over
  your spent InfoSec dollars
Why clients buy pentests?
• Want to test the security
   – The only true reason which is really rare
• Compliance
   – That mandates pentests
• Want to know the risks
   – Although there are much better and safer tools
• False compliance
   – That does not mandate pentests
• We were hacked!!
• Have no idea how else to ‘fix it’…
Why clients get/do bad pentests?
     What clients cannot affect
• Bad pentesters
  – Some pentesters just suck
• Most methodologies suck too
  – Remember your high school lessons
• Time/cost relation in consulting business
  models
  – Pentests are quick
  – ‘Quick’ means ‘cheap’
Why people get/do bad pentests?
      Clients can and do affect
• Lack of understanding the difference
  – Most buy a plain VA dressed as a sexy pentest
• Lack of understanding the reason
  – PCI pentest not to find vulns, you have ASV scan
    for that
• Lack of quality assurance
  – It takes to buy 2-3 bad pentest to understand
    they’re bad
• Validation panic
How to clean this s fix this
• Learn and understand the difference
  – Read the PT standards – there are plenty
     • PTES, OSSTMM, NIST, ISACA, ETC.
     • Reason which are good for you
  – Ask pentesters you know are really good
     • Twitter, mailing lists, security conferences…
• Learn and understand the reason
  – Define why are you doing this before posting a PO
  – Reason about it and choose the best you need
     • PT or VA
How else can we fix this?
• Change the payment rules
  – Create the list of objectives
  – Pay a ‘standard’ price for reformatted Qualys
    report Vulnerability Assessment
  – Pay a bonus for each objective in the list
• Choose good pentesters
  – Ask for papers (sample reports, certs, references)
     • NDA excuse is bull s irrelevant
  – Arrange demo exercises
     • (Good) pentesters love exercises
     • Honeypots are for free
How else can we fix this?
              (dirty tricks)
• Have nerve
  – Stress on the need of PT over VA or vice versa –
    based on your need
• Push on compliance
  – PCI Information Supplement 11.3
     • Requires the vulns to be exploited
     • Requires channel diversity: social, network, WiFi etc.
• Learn some skill yourself
  – It really helps
  – And it’s really fun
Something to Think About and Discuss
• Vuln Assessment covers a small portion of preventive controls
• PenTest delves into each and every control you have
• Assume you have no need in testing
  preventive controls… Just assume
• How can you test reactive and
  corrective controls?
Thank you… in advance!




           vlad@styran.com
   https://secureglaxy.blogspot.com
               @saprand

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Владимир Стыран - Пентест следующего поколения, который ваша компания не может себе позволить

  • 1. Vlad Styran Next Generation Pentest Your Company Cannot Buy why both consultants and customers are doing it wrong
  • 2. Who’s that guy? • Security Consultant for BMS Consulting • Social Engineering researcher • InfoSec blogger • Podcaster
  • 3. Why he is here? • Pentesting since 2006 – Web sites, banking systems, telecom, • X commercial pre-sale presentations – Saw client’s eyes BEFORE the test • X-Y pentest reports written – Saw client’s eyes AFTER the test – Writing reports is HELL • Z pentest reports read – Reading others’ reports is FUN • CISSP, CEH, CISA… – Because it rarely matters
  • 4. Why are YOU here? • This preso is for those who want a great pentest to be done – and someone to benefit from this pentest • usually it’s a company • You may be a customer • Or a consultant • Or both • And you should agree that there’s something wrong with pentesting industry
  • 5. Some definitions • What is a Penetration Test? • What is a Vulnerability Assessment? • What is the difference? • Why should anyone bother? • And let’s make it quick and simple
  • 6. Test • Testing is deeply interactive • A test is something a tester and what is tested do both – We act and see the reaction – Not just look, measure and record – We touch, push and kick – We challenge what we test • Test has a goal
  • 7. Penetration Test • Penetration is getting through obstacles: – Security systems – User awareness – Physical barriers • The pentest succeeds if we get through – And fails if we don’t • And this usually means right the opposite to client • The goal is virtually anything, but – Penetrate a system – Pwnz0r everything: DBA, root, Domain Admin – ‘Get’ the data to show it’s vulnerable – Show that the business might be stopped
  • 8. Vulnerability Assessment • Find all vulnerabilities – Remove false positives (optional) • And tell us how to fix them – Usually in couple of deferent ways • Don’t try to break anything, it might… break! • Come in few weeks (months?) and check how whether we fixed stuff
  • 9. The Difference • Deep interactivity: – Pentest is interactive to the very deep you can get – Vulnerability Assessment is superficial • The goal: – Pentest aims at a narrow goal – Vuln Assessment is as broad as client can pay for • The PenTest is focused and thorough • The VA is a mile broad and a feet deep • You can easily do VA yourself but PT isn’t easy – Not because it’s hard to do, because of conflict of interest
  • 10. More Difference • PT not just scans, it exploits • Most pentest standards do multiple channels – Systems and network – Wireless and telecom – Human interaction – Physical stuff • VA is purely technical – Systems and network – And maybe wireless… or telecom…
  • 11. That was ‘what’ and ‘how’. What about ‘why’? • And this is the most important and interesting part that everyone should know • Vulnerability Assessment: “Let us know how we can fix what is presumably already broken” • Penetration Test: “Try to break what is presumably unbreakable”* *Considering reasonable time and resources available
  • 12. Now To Work • Why clients buy pentests? • How consultants do pentests? • Why clients get bad pentests? • What can we do to fix it? – Clients – Pentesters
  • 13. How consultants do pentests? • We set the scope – Systems, locations, people, contacts etc. • We do recon – Short for ‘reconnaissance’ • We enumerate the targets – And search for vulnerabilities • It is pretty much the VA until this point
  • 14. How consultants do good pentests? • We validate the vulnerabilities – ‘Validate’ stand for ‘exploit’ since business people don’t like hacker jargon • We leverage access gained and pivot further – Into the network, into the sun, into the cookies… • We collect evidence of your data compromise – Without actually compromising the data – But enough to make your bosses like OMG
  • 15. How consultants do outstanding Pentest-NG? • We meet your business people beforehand – To know how your business lives – And research on how someone can kill it • We do all channels and vectors – We plan for HR interviews and local conferences – We write custom software and exploit code • We do virtually anything to make you cry over your spent InfoSec dollars
  • 16. Why clients buy pentests? • Want to test the security – The only true reason which is really rare • Compliance – That mandates pentests • Want to know the risks – Although there are much better and safer tools • False compliance – That does not mandate pentests • We were hacked!! • Have no idea how else to ‘fix it’…
  • 17. Why clients get/do bad pentests? What clients cannot affect • Bad pentesters – Some pentesters just suck • Most methodologies suck too – Remember your high school lessons • Time/cost relation in consulting business models – Pentests are quick – ‘Quick’ means ‘cheap’
  • 18. Why people get/do bad pentests? Clients can and do affect • Lack of understanding the difference – Most buy a plain VA dressed as a sexy pentest • Lack of understanding the reason – PCI pentest not to find vulns, you have ASV scan for that • Lack of quality assurance – It takes to buy 2-3 bad pentest to understand they’re bad • Validation panic
  • 19. How to clean this s fix this • Learn and understand the difference – Read the PT standards – there are plenty • PTES, OSSTMM, NIST, ISACA, ETC. • Reason which are good for you – Ask pentesters you know are really good • Twitter, mailing lists, security conferences… • Learn and understand the reason – Define why are you doing this before posting a PO – Reason about it and choose the best you need • PT or VA
  • 20. How else can we fix this? • Change the payment rules – Create the list of objectives – Pay a ‘standard’ price for reformatted Qualys report Vulnerability Assessment – Pay a bonus for each objective in the list • Choose good pentesters – Ask for papers (sample reports, certs, references) • NDA excuse is bull s irrelevant – Arrange demo exercises • (Good) pentesters love exercises • Honeypots are for free
  • 21. How else can we fix this? (dirty tricks) • Have nerve – Stress on the need of PT over VA or vice versa – based on your need • Push on compliance – PCI Information Supplement 11.3 • Requires the vulns to be exploited • Requires channel diversity: social, network, WiFi etc. • Learn some skill yourself – It really helps – And it’s really fun
  • 22. Something to Think About and Discuss • Vuln Assessment covers a small portion of preventive controls • PenTest delves into each and every control you have • Assume you have no need in testing preventive controls… Just assume • How can you test reactive and corrective controls?
  • 23. Thank you… in advance! vlad@styran.com https://secureglaxy.blogspot.com @saprand