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Beyond the Pentest
How C2, Internal Pivoting, and Data
Exfiltration Show True Risk
Beau Bullock
Beyond the Pentest
What does a standard internal network pentest already
cover?
Port scans
Vulnerability scanning
Manual validation
Provide recommendations
What is Wrong With This
Attackers don’t
vulnerability scan - too
noisy
Misses some very critical
vulnerabilities
Doesn’t account for
domain systems already
compromised
whoami
Beau Bullock
Pentester at Black Hills
Information Security
Host of Hack Naked TV
Previously an enterprise defender
OSCP, GXPN, GPEN, GCIH,
GCFA, OSWP and GSEC
What Are We Missing
Three major things
Command and Control
Internal Pivoting
Data Exfiltration
How Do We Test These
Start with the basics
Standard domain user account
Lowest level of access typically provisioned
Standard system build
Anyone on leave? Steal their system
Standard network access
Command and Control
Command and Control
Three focus areas
Payload delivery
Email, web, etc.
Client-based protections
AV, application whitelisting, HIDS, etc.
Network-based protections
Egress filtering, IDS/IPS, inline payload detonation
C2: Payload Delivery
What can be emailed to your employees?
Executable
PDF
Word DOC or XLS w/ macro
Batch file
Encrypted ZIP
Extensionless files?
C2: Payload Delivery
Protip:
Many webmail services scan attachments for
malware
Some don’t allow EXE’s altogether
Yahoo’s MTA does not scan, and allows EXE’s
Use a third-party mail client to send through Yahoo
C2: Payload Delivery
What can be downloaded?
How about browser or Java or Adobe exploits?
Are users allowed to insert USB drives?
C2: Client-Based
Protections
Did anything detect the payload after entry?
Anti-Virus
Application whitelisting
SIEM alerts
C2: Client-Based
Protections
Payload types
Non-encoded EXE
Encoded EXE
ShellCode injection
Word Doc w/ macro
Software exploit
Physical access (rubber ducky)
C2: Client-Based
Protections
Bypassing Client-based protections
Veil-Evasion
Framework for creating custom malware
PowerSploit
Shellcode injection directly into memory
Obfuscation
C2: Network-Based
Protections
Was the C2 channel detected?
Firewall block
IDS/IPS detection
Inline Detonation
C2: Network-Based
Protections
What does an outbound portscan reveal?
open.zorinaq.com
Weak egress filtering provides more legroom for C2
DLP might miss items not sent over standard ports
C2: Some Typical C2
Channels
Standard TCP
HTTP/HTTPS
DNS
ICMP
C2: C2 Through A Web
Proxy
Meterpreter Reverse_https
Uses proxy settings on system
PowerShell Empire!!!
Same as above but in PowerShell
Appears as web traffic through your web proxy
C2: C2 Over Social Media
Can your users get to any social media sites?
Twittor - Uses Twitter direct messages as a C2
channel
GCAT - Uses Gmail as a C2 channel
Sneaky-Creeper - Uses Twitter, Tumblr, and
Soundcloud as a C2 channel
C2: C2 over DNS
DNScat
Tunnels traffic through DNS requests
C2 channel through NS Records
C2 even with EVERY port blocked outbound from the
client
https://github.com/iagox86/dnscat2
C2: C2 over ICMP
Invoke-PowerShellICMP
Tunnels traffic through ICMP echo-requests and
echo-replys
ICMP is commonly allowed through firewalls
https://github.com/samratashok/nishang/tree/master/Shells
Internal Pivoting
Internal Pivoting
Use built-in tools as a low level user to compromise a
network
No vuln scans needed
Less noise
Escalate privileges; locate sensitive data
Pivot: GPP Passwords
May 13, 2014 – MS14-025
Passwords of accounts set
by GPP are trivially
decrypted!
…by ANY authenticated
user on the domain
Located in groups.xml files
on SYSVOL
https://msdn.microsoft.com/en-us/library/2c15cbf0-f086-4c74-8b70-1f2fa45dd4be.aspx
http://blogs.technet.com/b/srd/archive/2014/05/13/ms14-025-an-update-for-group-policy-preferences.aspx
https://dirteam.com/sander/2014/05/23/security-thoughts-passwords-in-group-policy-preferences-cve-2014-1812/
Pivot: GPP Passwords
First thing I check for on an internal
assessment
Almost always find an admin
password here
Find it with:
PowerSploit - Get-
GPPPassword
Metasploit GPP Module
Or…
C:>findstr /S cpassword %logonserver%sysvol*.xml
Pivot: Privilege Escalation
Local privilege escalation
Are we already a local
admin?
PowerUp
Invoke-AllChecks looks
for potential privilege
escalation vectors
http://www.verisgroup.com/2014/06/17/powerup-usage/
Pivot: Misconfigured
Systems
Occasionally, admins get lazy… and do things like add
“Domain Users” group to the “Local Administrators”
group
Pivot: Misconfigured
Systems
This means EVERY domain user is now is an
administrator of that system
Veil-PowerView Find-LocalAdminAccess
Veil-PowerView Invoke-ShareFinder
http://www.harmj0y.net/blog/penetesting/finding-local-admin-with-the-veil-framework/
Pivot: Password Spraying
Domain locks out accounts after a certain number of
failed logins
Can’t brute force
Solution:
Try a number of passwords less than the domain
lockout policy against EVERY account in the domain
Pivot: Password Spraying
Lockout Policy = Threshold of five
Let’s try one password across every account
What passwords do we try?
Password123
Companyname123
SeasonYear
C:>@FOR /F %n in (users.txt)
DO @FOR /F %p in (pass.txt) DO
@net use DOMAINCONTROLLER
IPC$ /user:DOMAIN%n %p 1>NUL
2>&1 && @echo [*] %n:%p &&
@net use /delete 
DOMAINCONTROLLERIPC$ > NUL
Pivot: Password Spraying
Pivot: LLMNR & NBTNS
Poison
LLMNR = Link-Local Multicast Name Resolution
NBT-NS = NetBIOS over TCP/IP Name Service
Both help hosts identify each other when DNS fails
Pivot: LLMNR & NBTNS
Poison
http://www.sternsecurity.com/blog/local-network-attacks-llmnr-and-nbt-ns-poisoning
Pivot: LLMNR & NBTNS
Poison
SpiderLabs Responder
Inveigh PowerShell Script
The result is that we obtain NTLM challenge/response
hashes
Crack hashes
https://www.trustwave.com/Resources/SpiderLabs-Blog/Introducing-Responder-1-0/
Sensitive Data Hunt
Sensitive Data: Info
Disclosure on Shares
Sensitive files on shares?
Find them with PowerView
ShareFinder then FileFinder
FileFinder will find files with the following
strings in their title:
‘*pass*’, ‘*sensitive*’, ‘*admin*’,
‘*secret*’, ‘*login*’, ‘*unattend*.xml’,
‘*.vmdk’, ‘*creds*’, or ‘*credential*’ 
Sensitive Data: Locate RDP
Jump Hosts
Where are users RDP’ing to?
Can provide insight into where critical systems are
Get-NetComputers | Get-NetRDPSessions | Export-
Csv –NoTypeInformation rdpsessions.csv
http://www.harmj0y.net/blog/powershell/powerquinsta/
Sensitive Data: Virtualization
Hypervisors
Data Exfiltration
Data Exfiltration
What are organizations concerned about leaving their
networks? 
PCI data
Patient health information
Personally Identifying Information
Intellectual property
Data Exfiltration
How can attackers get data out of your network? 
Email
Web Access
USB Drive
Photo
Data Exfil: Email
For email is DLP being enforced on the following?
Cleartext in email body
Encoded in email body
Attachments
Optical Character Recognition
Data Exfil: Web	
Is all web traffic subject to DLP inspection?
Same types of tests as email are performed but
tracking over standard and non-standard web ports
Data Exfil: USB Drives
Are files allowed to be copied to a USB drive?
Encryption
DLP
Blocked completely
Putting It All Together
Attack Scenario
Target Organization Setup
Firewall only allows outbound traffic through web
proxy
AV up to date on clients
Email gateway allows Doc files
Local Administrator account is widespread with same
credentials
Attack Scenario
Phishing email is crafted with Word doc attachment
Word doc is weaponized with a Macro
Email is sent to target employee
Attack Scenario
Employee opens email
Downloads attached .doc
Enables content
Macro runs PowerSploit
PowerShell script to inject
Meterpreter Reverse_https
into memory
Meterpreter C2 channel is
established
Attack Scenario
Password spray from the command line
Spring2016?
Run Find-LocalAdminAccess to find where the users
are local admin
Pivot using psexec
Attack Scenario
Attacker dumps local user hashes (including local
admin)
Local administrator credential is not randomized
Using PowerView UserHunter the attacker finds where
Domain Admins are located
Attack Scenario
Attacker pivots to DA
workstation
Runs Mimikatz to dump
creds from memory
Locates sensitive data
with PowerView
ShareFinder
Exfils data
Summary
Summary
What are the benefits of this style of testing?
Real test of detection and incident response
Shows how an attacker can go from low access to
owning the environment
Shows true risk to the organization
Thank You!
beau@blackhillsinfosec.com
beau@dafthack.com
@dafthack

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Beyond the Pentest: How C2, Internal Pivoting, and Data Exfiltration Show True Risk

  • 1. Beyond the Pentest How C2, Internal Pivoting, and Data Exfiltration Show True Risk Beau Bullock
  • 2. Beyond the Pentest What does a standard internal network pentest already cover? Port scans Vulnerability scanning Manual validation Provide recommendations
  • 3. What is Wrong With This Attackers don’t vulnerability scan - too noisy Misses some very critical vulnerabilities Doesn’t account for domain systems already compromised
  • 4. whoami Beau Bullock Pentester at Black Hills Information Security Host of Hack Naked TV Previously an enterprise defender OSCP, GXPN, GPEN, GCIH, GCFA, OSWP and GSEC
  • 5. What Are We Missing Three major things Command and Control Internal Pivoting Data Exfiltration
  • 6. How Do We Test These Start with the basics Standard domain user account Lowest level of access typically provisioned Standard system build Anyone on leave? Steal their system Standard network access
  • 8. Command and Control Three focus areas Payload delivery Email, web, etc. Client-based protections AV, application whitelisting, HIDS, etc. Network-based protections Egress filtering, IDS/IPS, inline payload detonation
  • 9. C2: Payload Delivery What can be emailed to your employees? Executable PDF Word DOC or XLS w/ macro Batch file Encrypted ZIP Extensionless files?
  • 10. C2: Payload Delivery Protip: Many webmail services scan attachments for malware Some don’t allow EXE’s altogether Yahoo’s MTA does not scan, and allows EXE’s Use a third-party mail client to send through Yahoo
  • 11. C2: Payload Delivery What can be downloaded? How about browser or Java or Adobe exploits? Are users allowed to insert USB drives?
  • 12. C2: Client-Based Protections Did anything detect the payload after entry? Anti-Virus Application whitelisting SIEM alerts
  • 13. C2: Client-Based Protections Payload types Non-encoded EXE Encoded EXE ShellCode injection Word Doc w/ macro Software exploit Physical access (rubber ducky)
  • 14. C2: Client-Based Protections Bypassing Client-based protections Veil-Evasion Framework for creating custom malware PowerSploit Shellcode injection directly into memory Obfuscation
  • 15. C2: Network-Based Protections Was the C2 channel detected? Firewall block IDS/IPS detection Inline Detonation
  • 16. C2: Network-Based Protections What does an outbound portscan reveal? open.zorinaq.com Weak egress filtering provides more legroom for C2 DLP might miss items not sent over standard ports
  • 17. C2: Some Typical C2 Channels Standard TCP HTTP/HTTPS DNS ICMP
  • 18. C2: C2 Through A Web Proxy Meterpreter Reverse_https Uses proxy settings on system PowerShell Empire!!! Same as above but in PowerShell Appears as web traffic through your web proxy
  • 19.
  • 20. C2: C2 Over Social Media Can your users get to any social media sites? Twittor - Uses Twitter direct messages as a C2 channel GCAT - Uses Gmail as a C2 channel Sneaky-Creeper - Uses Twitter, Tumblr, and Soundcloud as a C2 channel
  • 21.
  • 22. C2: C2 over DNS DNScat Tunnels traffic through DNS requests C2 channel through NS Records C2 even with EVERY port blocked outbound from the client https://github.com/iagox86/dnscat2
  • 23.
  • 24. C2: C2 over ICMP Invoke-PowerShellICMP Tunnels traffic through ICMP echo-requests and echo-replys ICMP is commonly allowed through firewalls https://github.com/samratashok/nishang/tree/master/Shells
  • 25.
  • 27. Internal Pivoting Use built-in tools as a low level user to compromise a network No vuln scans needed Less noise Escalate privileges; locate sensitive data
  • 28. Pivot: GPP Passwords May 13, 2014 – MS14-025 Passwords of accounts set by GPP are trivially decrypted! …by ANY authenticated user on the domain Located in groups.xml files on SYSVOL https://msdn.microsoft.com/en-us/library/2c15cbf0-f086-4c74-8b70-1f2fa45dd4be.aspx http://blogs.technet.com/b/srd/archive/2014/05/13/ms14-025-an-update-for-group-policy-preferences.aspx https://dirteam.com/sander/2014/05/23/security-thoughts-passwords-in-group-policy-preferences-cve-2014-1812/
  • 29. Pivot: GPP Passwords First thing I check for on an internal assessment Almost always find an admin password here Find it with: PowerSploit - Get- GPPPassword Metasploit GPP Module Or… C:>findstr /S cpassword %logonserver%sysvol*.xml
  • 30. Pivot: Privilege Escalation Local privilege escalation Are we already a local admin? PowerUp Invoke-AllChecks looks for potential privilege escalation vectors http://www.verisgroup.com/2014/06/17/powerup-usage/
  • 31. Pivot: Misconfigured Systems Occasionally, admins get lazy… and do things like add “Domain Users” group to the “Local Administrators” group
  • 32. Pivot: Misconfigured Systems This means EVERY domain user is now is an administrator of that system Veil-PowerView Find-LocalAdminAccess Veil-PowerView Invoke-ShareFinder http://www.harmj0y.net/blog/penetesting/finding-local-admin-with-the-veil-framework/
  • 33. Pivot: Password Spraying Domain locks out accounts after a certain number of failed logins Can’t brute force Solution: Try a number of passwords less than the domain lockout policy against EVERY account in the domain
  • 34. Pivot: Password Spraying Lockout Policy = Threshold of five Let’s try one password across every account What passwords do we try? Password123 Companyname123 SeasonYear C:>@FOR /F %n in (users.txt) DO @FOR /F %p in (pass.txt) DO @net use DOMAINCONTROLLER IPC$ /user:DOMAIN%n %p 1>NUL 2>&1 && @echo [*] %n:%p && @net use /delete DOMAINCONTROLLERIPC$ > NUL
  • 36. Pivot: LLMNR & NBTNS Poison LLMNR = Link-Local Multicast Name Resolution NBT-NS = NetBIOS over TCP/IP Name Service Both help hosts identify each other when DNS fails
  • 37. Pivot: LLMNR & NBTNS Poison http://www.sternsecurity.com/blog/local-network-attacks-llmnr-and-nbt-ns-poisoning
  • 38. Pivot: LLMNR & NBTNS Poison SpiderLabs Responder Inveigh PowerShell Script The result is that we obtain NTLM challenge/response hashes Crack hashes https://www.trustwave.com/Resources/SpiderLabs-Blog/Introducing-Responder-1-0/
  • 40. Sensitive Data: Info Disclosure on Shares Sensitive files on shares? Find them with PowerView ShareFinder then FileFinder FileFinder will find files with the following strings in their title: ‘*pass*’, ‘*sensitive*’, ‘*admin*’, ‘*secret*’, ‘*login*’, ‘*unattend*.xml’, ‘*.vmdk’, ‘*creds*’, or ‘*credential*’ 
  • 41. Sensitive Data: Locate RDP Jump Hosts Where are users RDP’ing to? Can provide insight into where critical systems are Get-NetComputers | Get-NetRDPSessions | Export- Csv –NoTypeInformation rdpsessions.csv http://www.harmj0y.net/blog/powershell/powerquinsta/
  • 44. Data Exfiltration What are organizations concerned about leaving their networks?  PCI data Patient health information Personally Identifying Information Intellectual property
  • 45. Data Exfiltration How can attackers get data out of your network?  Email Web Access USB Drive Photo
  • 46. Data Exfil: Email For email is DLP being enforced on the following? Cleartext in email body Encoded in email body Attachments Optical Character Recognition
  • 47. Data Exfil: Web Is all web traffic subject to DLP inspection? Same types of tests as email are performed but tracking over standard and non-standard web ports
  • 48. Data Exfil: USB Drives Are files allowed to be copied to a USB drive? Encryption DLP Blocked completely
  • 49. Putting It All Together
  • 50. Attack Scenario Target Organization Setup Firewall only allows outbound traffic through web proxy AV up to date on clients Email gateway allows Doc files Local Administrator account is widespread with same credentials
  • 51. Attack Scenario Phishing email is crafted with Word doc attachment Word doc is weaponized with a Macro Email is sent to target employee
  • 52. Attack Scenario Employee opens email Downloads attached .doc Enables content Macro runs PowerSploit PowerShell script to inject Meterpreter Reverse_https into memory Meterpreter C2 channel is established
  • 53. Attack Scenario Password spray from the command line Spring2016? Run Find-LocalAdminAccess to find where the users are local admin Pivot using psexec
  • 54. Attack Scenario Attacker dumps local user hashes (including local admin) Local administrator credential is not randomized Using PowerView UserHunter the attacker finds where Domain Admins are located
  • 55. Attack Scenario Attacker pivots to DA workstation Runs Mimikatz to dump creds from memory Locates sensitive data with PowerView ShareFinder Exfils data
  • 56.
  • 58. Summary What are the benefits of this style of testing? Real test of detection and incident response Shows how an attacker can go from low access to owning the environment Shows true risk to the organization