© 2018 Denim Group – All Rights Reserved
Building a world where technology is trusted.
Reducing Attack Surface in Budget
Constrained Environments
John B. Dickson, CISSP #4649
@johnbdickson
© 2018 Denim Group – All Rights Reserved
Background
• AFCERT Analyst
• 20+ Year Security Professional
• Denim Group Principal
• ISSA Distinguished Fellow
• Security Conference Speaker
• Dark Reading Columnist
© 2018 Denim Group – All Rights Reserved
Denim Group | Company Background
• Trusted advisor on all matters of software risk
• External application & network assessments
• Web, mobile, and cloud
• Software development lifecycle development (SDLC) consulting
• Network and infrastructure where applications reside
• Managed security services
• Developed
© 2018 Denim Group – All Rights Reserved
The Conventional Network
4
© 2018 Denim Group – All Rights Reserved
The Evolving Enterprise
5
© 2018 Denim Group – All Rights Reserved
The New Network
6
© 2018 Denim Group – All Rights Reserved
Increasing External Pressures & Threats
There are two types of organizations in the world…
1. Targeted
2. Targets of Opportunity
1. 2/3 of all attacks go undetected
2. Leading cause: inadvertent activity
If you are not #1, your challenge is to not become #2
7
© 2018 Denim Group – All Rights Reserved
Increasing External Pressures & Threats
Commercialization and Specialization of the Threat
• Sophisticated marketplace of underground suppliers
• Increased specialization of threat actors
• Malware developers
• Call centers
• Card scammers
• “Verticalization” of the Threat
• Ability to adapt and capitalize on current events more quickly
8
© 2018 Denim Group – All Rights Reserved
Increasing External Pressures & Threats
Sophisticated Malware and Ransomeware
• Sophisticated marketplace drives more responsive attacks
able to adapt and scale
• Ability to highly automate attacks expands attack footprint
• Sophisticated attacks no longer the worry of the largest
organizations
• Focus back on availability for the SMB, which has always
been a challenge
9
© 2018 Denim Group – All Rights Reserved
Security Budgets: The Starting Point
• Some have lost the game before getting on the
field
• Competing Against:
• Company pet projects
• Legacy support requirements
• Current events
• Information security as the “silent service” –
Rich Baich, Wells Fargo CISO
• Source: “Winning as a CISO,” Rich Baich
© 2018 Denim Group – All Rights Reserved
Getting Your Security Budget
Approved Without FUD
• Exploit Pet Projects
• Account for Culture
• Tailor to Your Specific Vertical
• Consciously Cultivate Credibility and Relationships
• Capitalize on Timely Events
• Capture Successes & Over-Communicate
Source: RSA 2014 “Getting Your Security Budget Approved Without FUD
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• Two Dimensions:
• Perception of Software Attack Surface
• Insight into Exposed Assets
12
Perception
Insight
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• As perception of the problem of attack surface widens the
scope of the problem increases
13
Perception
Insight
Web
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• As perception of the problem of attack surface widens the
scope of the problem increases
14
Perception
Insight
Web
Applications
Client-Server
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• As perception of the problem of attack surface widens the
scope of the problem increases
15
Perception
Insight
Web
Applications
Client-Server
Applications
Desktop
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• As perception of the problem of attack surface widens the
scope of the problem increases
16
Perception
Insight
Web
Applications
Client-Server
Applications
Desktop
Applications
Cloud
Applications
and Services
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• As perception of the problem of attack surface widens the
scope of the problem increases
17
Perception
Insight
Web
Applications
Client-Server
Applications
Desktop
Applications
Cloud
Applications
and Services
Mobile
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• Discovery activities increase insight
18
Perception
Insight
Web
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• Discovery activities increase insight
19
Perception
Insight
Web
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• Discovery activities increase insight
20
Perception
Insight
Web
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• Over time you end up with a progression
21
Perception
Insight
Web
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• Over time you end up with a progression
22
Perception
Insight
Web
Applications
Client-Server
Applications
© 2018 Denim Group – All Rights Reserved
Desktop
Applications
Client-Server
Applications
Attack Surface: The Security Officer’s Journey
• Over time you end up with a progression
23
Perception
Insight
Web
Applications
© 2018 Denim Group – All Rights Reserved
Desktop
Applications
Client-Server
Applications
Attack Surface: The Security Officer’s Journey
• Over time you end up with a progression
24
Perception
Insight
Web
Applications
Cloud
Applications
and Services
© 2018 Denim Group – All Rights Reserved
Desktop
Applications
Client-Server
Applications
Attack Surface: The Security Officer’s Journey
• Over time you end up with a progression
25
Perception
Insight
Web
Applications
Cloud
Applications
and Services
Mobile
Applications
© 2018 Denim Group – All Rights Reserved
Attack Surface: The Security Officer’s Journey
• When you reach this point it is called “enlightenment”
• You won’t reach this point
26
Perception
Insight
Web
Applications
Client-Server
Applications
Desktop
Applications
Cloud
Applications
and Services
Mobile
Applications
© 2018 Denim Group – All Rights Reserved
27
• Understand your Attack Surface -
General
• …and where your company’s most sensitive
client data lives
• Tailor rigorous testing to agreed-upon threat
• Don’t forget mobile/cloud/social media
• Regularly conduct penetration tests mimicking
your most likely threat
Suggested Strategy #1
© 2018 Denim Group – All Rights Reserved
28
• Understand your Attack Surface - External
• Conduct monthly (or quarterly) network and
application vulnerability tests to eliminate most
obvious vulnerabilities
• Consider quarterly phishing campaigns using
context from firm clients
• Review DNS registry & shared secret
• Conduct social engineering exercise with firm
leadership buy-in
• Identify 3rd
-party network connections or
federated trust relationships
Suggested Strategy #1
(Continued)
© 2018 Denim Group – All Rights Reserved
29
• Protect Information at Rest and in Transit
• Tailor DLP to organization’s needs
• Implement at desktop, gateway, or federated entry points
• Disable USBs through technology acquisition or
Active Directory (AD) Group Policy Objects (GPO)
• Example: IEEE 802.1X-authenticated wired connections
through Group Policy
• Implement trusted sys logging for admins
• Test portal authorization implementation with manual
testing
• Secure 3rd
-party FTP or mail service for most
sensitive documents (obviously)
Suggested Strategy #2
© 2018 Denim Group – All Rights Reserved
30
• Protect Information at Rest and in
Transit
• Rollout mobile device management for all
mobile devices implementing:
• Remote wipe, OTA Updates, Containers etc.
• Deploy full disk encryption on ALL laptops
• Rollout next-generation anti-virus and
malware detection
• Enable alerting for key events
Suggested Strategy #2 (Continued)
© 2018 Denim Group – All Rights Reserved
31
• Protect Information at Rest and in
Transit
• Consider 2-factor authentication or tokens for:
• Administrative accounts
• Particularly sensitive client documents
• And don’t forget! Implement encrypted email
at all times!
Suggested Strategy #2 (Even more!)
© 2018 Denim Group – All Rights Reserved
32
• Reduce your External Attack Surface
• Implement organization-wide patching
• Understand risks of 3rd-party risks of CMS or
portal software
• Catalog trusted entry points from 3rd parties
• Ensure your web-facing sites are devoid of
SQL injections/XSS vulnerabilities
• Start to build a “defense in depth” approach to
your organization
Suggested Strategy #3
© 2018 Denim Group – All Rights Reserved
33
• Be Able to Identify an Attack
• Deeply understand your “base” network and
application operations tempo
• Do you regularly monitor network stats?
• Build the competency to regularly review key
events via logging
• IPS/IDS + SEM if you’re big enough to
warrant capability
• Exfiltration logging for after the fact
Suggested Strategy #4
© 2018 Denim Group – All Rights Reserved
34
• Don’t go it alone!
• Gain and maintain a trusted relationship with
an organization that understands firm risk and
can conduct knowledge transfer
• Particularly given the broad technology stack
• Consider a Managed Security Services
Provider (MSSP) for 24/7 coverage
• Have a relationship with an IR and crisis
communication firm.
Suggested Strategy #5
© 2018 Denim Group – All Rights Reserved
Why Is this Important to You?
• Budget will remain constrained
• Threats adapting and metastasizing faster than defenders
can respond
• Attack surface is constantly in flux
© 2018 Denim Group – All Rights Reserved
John B. Dickson, CISSP
@johnbdickson
www.denimgroup.com
Questions and Answers

Reducing Attack Surface in Budget Constrained Environments

  • 1.
    © 2018 DenimGroup – All Rights Reserved Building a world where technology is trusted. Reducing Attack Surface in Budget Constrained Environments John B. Dickson, CISSP #4649 @johnbdickson
  • 2.
    © 2018 DenimGroup – All Rights Reserved Background • AFCERT Analyst • 20+ Year Security Professional • Denim Group Principal • ISSA Distinguished Fellow • Security Conference Speaker • Dark Reading Columnist
  • 3.
    © 2018 DenimGroup – All Rights Reserved Denim Group | Company Background • Trusted advisor on all matters of software risk • External application & network assessments • Web, mobile, and cloud • Software development lifecycle development (SDLC) consulting • Network and infrastructure where applications reside • Managed security services • Developed
  • 4.
    © 2018 DenimGroup – All Rights Reserved The Conventional Network 4
  • 5.
    © 2018 DenimGroup – All Rights Reserved The Evolving Enterprise 5
  • 6.
    © 2018 DenimGroup – All Rights Reserved The New Network 6
  • 7.
    © 2018 DenimGroup – All Rights Reserved Increasing External Pressures & Threats There are two types of organizations in the world… 1. Targeted 2. Targets of Opportunity 1. 2/3 of all attacks go undetected 2. Leading cause: inadvertent activity If you are not #1, your challenge is to not become #2 7
  • 8.
    © 2018 DenimGroup – All Rights Reserved Increasing External Pressures & Threats Commercialization and Specialization of the Threat • Sophisticated marketplace of underground suppliers • Increased specialization of threat actors • Malware developers • Call centers • Card scammers • “Verticalization” of the Threat • Ability to adapt and capitalize on current events more quickly 8
  • 9.
    © 2018 DenimGroup – All Rights Reserved Increasing External Pressures & Threats Sophisticated Malware and Ransomeware • Sophisticated marketplace drives more responsive attacks able to adapt and scale • Ability to highly automate attacks expands attack footprint • Sophisticated attacks no longer the worry of the largest organizations • Focus back on availability for the SMB, which has always been a challenge 9
  • 10.
    © 2018 DenimGroup – All Rights Reserved Security Budgets: The Starting Point • Some have lost the game before getting on the field • Competing Against: • Company pet projects • Legacy support requirements • Current events • Information security as the “silent service” – Rich Baich, Wells Fargo CISO • Source: “Winning as a CISO,” Rich Baich
  • 11.
    © 2018 DenimGroup – All Rights Reserved Getting Your Security Budget Approved Without FUD • Exploit Pet Projects • Account for Culture • Tailor to Your Specific Vertical • Consciously Cultivate Credibility and Relationships • Capitalize on Timely Events • Capture Successes & Over-Communicate Source: RSA 2014 “Getting Your Security Budget Approved Without FUD
  • 12.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • Two Dimensions: • Perception of Software Attack Surface • Insight into Exposed Assets 12 Perception Insight
  • 13.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • As perception of the problem of attack surface widens the scope of the problem increases 13 Perception Insight Web Applications
  • 14.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • As perception of the problem of attack surface widens the scope of the problem increases 14 Perception Insight Web Applications Client-Server Applications
  • 15.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • As perception of the problem of attack surface widens the scope of the problem increases 15 Perception Insight Web Applications Client-Server Applications Desktop Applications
  • 16.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • As perception of the problem of attack surface widens the scope of the problem increases 16 Perception Insight Web Applications Client-Server Applications Desktop Applications Cloud Applications and Services
  • 17.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • As perception of the problem of attack surface widens the scope of the problem increases 17 Perception Insight Web Applications Client-Server Applications Desktop Applications Cloud Applications and Services Mobile Applications
  • 18.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • Discovery activities increase insight 18 Perception Insight Web Applications
  • 19.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • Discovery activities increase insight 19 Perception Insight Web Applications
  • 20.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • Discovery activities increase insight 20 Perception Insight Web Applications
  • 21.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • Over time you end up with a progression 21 Perception Insight Web Applications
  • 22.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • Over time you end up with a progression 22 Perception Insight Web Applications Client-Server Applications
  • 23.
    © 2018 DenimGroup – All Rights Reserved Desktop Applications Client-Server Applications Attack Surface: The Security Officer’s Journey • Over time you end up with a progression 23 Perception Insight Web Applications
  • 24.
    © 2018 DenimGroup – All Rights Reserved Desktop Applications Client-Server Applications Attack Surface: The Security Officer’s Journey • Over time you end up with a progression 24 Perception Insight Web Applications Cloud Applications and Services
  • 25.
    © 2018 DenimGroup – All Rights Reserved Desktop Applications Client-Server Applications Attack Surface: The Security Officer’s Journey • Over time you end up with a progression 25 Perception Insight Web Applications Cloud Applications and Services Mobile Applications
  • 26.
    © 2018 DenimGroup – All Rights Reserved Attack Surface: The Security Officer’s Journey • When you reach this point it is called “enlightenment” • You won’t reach this point 26 Perception Insight Web Applications Client-Server Applications Desktop Applications Cloud Applications and Services Mobile Applications
  • 27.
    © 2018 DenimGroup – All Rights Reserved 27 • Understand your Attack Surface - General • …and where your company’s most sensitive client data lives • Tailor rigorous testing to agreed-upon threat • Don’t forget mobile/cloud/social media • Regularly conduct penetration tests mimicking your most likely threat Suggested Strategy #1
  • 28.
    © 2018 DenimGroup – All Rights Reserved 28 • Understand your Attack Surface - External • Conduct monthly (or quarterly) network and application vulnerability tests to eliminate most obvious vulnerabilities • Consider quarterly phishing campaigns using context from firm clients • Review DNS registry & shared secret • Conduct social engineering exercise with firm leadership buy-in • Identify 3rd -party network connections or federated trust relationships Suggested Strategy #1 (Continued)
  • 29.
    © 2018 DenimGroup – All Rights Reserved 29 • Protect Information at Rest and in Transit • Tailor DLP to organization’s needs • Implement at desktop, gateway, or federated entry points • Disable USBs through technology acquisition or Active Directory (AD) Group Policy Objects (GPO) • Example: IEEE 802.1X-authenticated wired connections through Group Policy • Implement trusted sys logging for admins • Test portal authorization implementation with manual testing • Secure 3rd -party FTP or mail service for most sensitive documents (obviously) Suggested Strategy #2
  • 30.
    © 2018 DenimGroup – All Rights Reserved 30 • Protect Information at Rest and in Transit • Rollout mobile device management for all mobile devices implementing: • Remote wipe, OTA Updates, Containers etc. • Deploy full disk encryption on ALL laptops • Rollout next-generation anti-virus and malware detection • Enable alerting for key events Suggested Strategy #2 (Continued)
  • 31.
    © 2018 DenimGroup – All Rights Reserved 31 • Protect Information at Rest and in Transit • Consider 2-factor authentication or tokens for: • Administrative accounts • Particularly sensitive client documents • And don’t forget! Implement encrypted email at all times! Suggested Strategy #2 (Even more!)
  • 32.
    © 2018 DenimGroup – All Rights Reserved 32 • Reduce your External Attack Surface • Implement organization-wide patching • Understand risks of 3rd-party risks of CMS or portal software • Catalog trusted entry points from 3rd parties • Ensure your web-facing sites are devoid of SQL injections/XSS vulnerabilities • Start to build a “defense in depth” approach to your organization Suggested Strategy #3
  • 33.
    © 2018 DenimGroup – All Rights Reserved 33 • Be Able to Identify an Attack • Deeply understand your “base” network and application operations tempo • Do you regularly monitor network stats? • Build the competency to regularly review key events via logging • IPS/IDS + SEM if you’re big enough to warrant capability • Exfiltration logging for after the fact Suggested Strategy #4
  • 34.
    © 2018 DenimGroup – All Rights Reserved 34 • Don’t go it alone! • Gain and maintain a trusted relationship with an organization that understands firm risk and can conduct knowledge transfer • Particularly given the broad technology stack • Consider a Managed Security Services Provider (MSSP) for 24/7 coverage • Have a relationship with an IR and crisis communication firm. Suggested Strategy #5
  • 35.
    © 2018 DenimGroup – All Rights Reserved Why Is this Important to You? • Budget will remain constrained • Threats adapting and metastasizing faster than defenders can respond • Attack surface is constantly in flux
  • 36.
    © 2018 DenimGroup – All Rights Reserved John B. Dickson, CISSP @johnbdickson www.denimgroup.com Questions and Answers