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Between You Me And The Network Security Boundary
Introduction
2
Patrick Fussell
pfussell@paysw.com
@pfizzell
http://lo-sec.ninja
3
I work for…
http://www.paysw.com/
Introduction: This Presentation
Agenda:
• Establish some common ground
• Review some common implementations
• Secure design concepts
4
Some Common Ground
5
Stuff I’m
Talking About
Things You
Think I’m
Talking About
A Venn Diagram of This Talk
Some Common Ground
6
Stuff I’m
Talking About
Things You
Think I’m
Talking About
A Venn Diagram of This Talk
Some Common Ground
7
Marketing
Call Center
HR
Wireless
Production
Typical Penetration Test
Some Common Ground
8
Stuff gets hacked
Some Common Ground
9
Marketing
Call Center
HR
IT
Production
Security Zones
Some Common Ground
10
Marketing
Call Center
HR
IT
Production
Security Zones
Some Common Ground
11
Marketing
Call Center
HR
IT
Production
Security Zones
Some Common Implementations,
Flaws, and Bypasses
Common Implementations
13
• Nothing exists in a vacuum
• Simplified version of each implementation
• Firecall
• VPN
• Jumpbox
• VDI
• Cloud
Firecall
Common Implementation: Firecall
15PSC – Proprietary and Confidential. All Rights Reserved.
POKING HOLES
Granting Temporary Access
Allowing Designated Systems Access
Manual or Automated
Common Implementation: Firecall
16PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: Firecall
17PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: Firecall
18PSC – Proprietary and Confidential. All Rights Reserved.
Marketing
Call Center
HR
IT
Production
Attacker
Common Implementation: Firecall
19PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: Firecall
20PSC – Proprietary and Confidential. All Rights Reserved.
Hacking 101: How to Pivot
Marketing
Call Center
HR
IT
Production
Attacker
Target Network
10.1.13.0/24
Common Implementation: Firecall
21PSC – Proprietary and Confidential. All Rights Reserved.
• Overall…not ideal
• Limiting exposure is tricky
• If this is your model
• Separate High-Security User Systems
• Build in Auto-Close
• Short time windows
• Regular testing and confirmation of changes
Takeaways:
• Firecall
• VPN
• Jumpbox
• VDI
• Cloud
VPN
Common Implementation: VPN
23PSC – Proprietary and Confidential. All Rights Reserved.
Office/Corporate Network Remote/Production NetworkInternet
Split Tunnel
Common Implementation: VPN
24PSC – Proprietary and Confidential. All Rights Reserved.
en0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
ether a4:5e:60:f0:4e:83
inet6 fe80::1c13:257b:625b:46ec%en0 prefixlen 64 secured scopeid 0x4
inet 192.168.0.199 netmask 0xffffff00 broadcast 192.168.0.255
nd6 options=201<PERFORMNUD,DAD>
media: autoselect
status: active
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1500
inet 172.16.25.114 --> 172.16.25.114 netmask 0xffffff00
Common Implementation: VPN
25PSC – Proprietary and Confidential. All Rights Reserved.
Office/Corporate Network Remote/Production NetworkInternet
Full Tunnel
Common Implementation: VPN
26PSC – Proprietary and Confidential. All Rights Reserved.
Wait for shellz!
Common Implementation: VPN
27PSC – Proprietary and Confidential. All Rights Reserved.
Takeaways:
• Again…alone this has some inherent weaknesses
• Split tunnel: Creates a direct bridge
• Full tunnel: Create an indirect bridge between zones
• Firecall
• VPN
• Jumpbox
• VDI
• Cloud
Jumpbox
Jumpbox
Common Implementation: Jumpbox
29PSC – Proprietary and Confidential. All Rights Reserved.
User VLAN Production
Systems
Authentication Boundary
Network Boundary
notsecure.org secure.local secure.local
Jumpbox
Common Implementation: Jumpbox
30PSC – Proprietary and Confidential. All Rights Reserved.
User VLAN Production
Systems
Authentication Boundary
notsecure.org notsecure.org notsecure.org
Domain
Controller
Common Implementation: Jumpbox
31PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: Jumpbox
32PSC – Proprietary and Confidential. All Rights Reserved.
JumpboxUser VLAN Production
Systems
notsecure.org secure.local secure.local
MFA
+
Common Implementation: Jumpbox
33PSC – Proprietary and Confidential. All Rights Reserved.
Discover RSA Management
Console
Login with local or domain
account
Profit
Common Implementation: Jumpbox
34PSC – Proprietary and Confidential. All Rights Reserved.
https://youtu.be/nzSG9f8ktTA
Practical Attacks Against Multifactor – Josh Stone
Derbycon 2015
Common Implementation: Jumpbox
35PSC – Proprietary and Confidential. All Rights Reserved.
Takeaways:
• Jumpbox with MFA is a solid approach to separating zones
• Avoid tying zones together with a single authentication domain
• Protect the users that access high-security zones
• Firecall
• VPN
• Jumpbox
• VDI
• Cloud
VDI
Common Implementation: VDI
37PSC – Proprietary and Confidential. All Rights Reserved.
VDI ServerUser VLAN Production
Systems
notsecure.org secure.local secure.local
MFA
+
Common Implementation: VDI
38PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: VDI
39PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: VDI
40PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: VDI
41PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: VDI
42PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: VDI
43PSC – Proprietary and Confidential. All Rights Reserved.
Takeaways:
• High tech solutions suffer from the same security challenges
• Using signed certificates for internally facing services matters
• Firecall
• VPN
• Jumpbox
• VDI
• Cloud
Cloud
Common Implementation: Cloud
45PSC – Proprietary and Confidential. All Rights Reserved.
Common Implementation: Cloud
46PSC – Proprietary and Confidential. All Rights Reserved.
PSC – Proprietary and Confidential. All Rights Reserved. 47
Common Implementation: Cloud
PSC – Proprietary and Confidential. All Rights Reserved. 48
Common Implementation: Cloud
PSC – Proprietary and Confidential. All Rights Reserved. 49
Common Implementation: Cloud
PSC – Proprietary and Confidential. All Rights Reserved. 50
Common Implementation: Cloud
Takeaways:
• Where are the boundaries?
• The cloud requires rigor
• Know your boundaries
Secure Design Concepts
Some Common Ground
52PSC – Proprietary and Confidential. All Rights Reserved.
Clean Source Principle
control a system
control everything that system controls
Secure Design Patterns
53PSC – Proprietary and Confidential. All Rights Reserved.
User Accessing
Privileged Resources
Servers in High-Sec
Environment
Attacker
Clean Source
Secure Design Patterns
54PSC – Proprietary and Confidential. All Rights Reserved.
Secure Access Workstations
High-security Channel
Low-security Channel
Secure Design Patterns
55PSC – Proprietary and Confidential. All Rights Reserved.
Careful Use of Administrative Privileges
Admin
Creds
Secure Design Patterns
56PSC – Proprietary and Confidential. All Rights Reserved.
Avoid Exceptions
• My goals:
– Present a secure architecture
– Bad guy perspective
– Give some insight that I have gained
• Shortcomings
– The reality of any implementation is very complex
– You could write a book about some of these topics
Summary
PSC – Proprietary and Confidential. All Rights Reserved. 57
• My favorite part of talking at a conference is talking to
people after I’ve delivered my presentation
– I get to learn new things
• I’m lonely, please come talk to me
– Or at least send me messages on twitter
Questions
PSC – Proprietary and Confidential. All Rights Reserved. 58
Patrick Fussell
pfussell@paysw.com
@pfizzell
http://lo-sec.ninja

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Between you me and the network security boundary