The document discusses the rise of PowerShell-based penetration testing tools and provides an overview of using PowerShell for various cyber attack techniques, including remote attacks, privilege escalation, and post-exploitation. It highlights specific tools and methods, such as PowerMeta for metadata extraction, MailSniper for email enumeration, and Invoke-Mimikatz for credential extraction, along with effective mitigations against these attacks. The conclusion emphasizes the ongoing power and adaptability of PowerShell in cyber threats while underscoring the need for enhanced defensive measures.

1. Pwning the Enterprise With
PowerShell
Beau Bullock -

2. Overview
• A dramatic increase in PowerShell-based pentesting tools
• Why use PowerShell?
• Signed Microsoft binary native to Windows systems
• Can execute code in memory avoiding AV detection
• Allows us to “Live off the land”
• Going to detail:
• A complete attack cycle using PowerShell
• Remote Attacks, C2, Privilege Escalation, Domain/Network/Post Exploitation
• Techniques for running PowerShell in locked down environments
• Some possible mitigations

3. whoami
• Pentester at Black Hills
Information Security
• Have a number of SANS and
OffSec certs…
• CitySec Meetup Organizer
• CigarCitySec – (Tampa, FL)
• CitrusSec – (Orlando, FL)
• Guitarist
• Avid OWA enthusiast

4. Remote Attacks
Attacks Against an External Network

5. PowerMeta
• Discover publicly available files
• Extract Metadata from them
• Can provide information about:
• The internal username schema
• System names
• Domain info
• Author(s)
• Beau Bullock (@dafthack)
• https://github.com/dafthack/PowerMeta

6. MailSniper
• Enumerate users/domain
• Password spray OWA/EWS
• Get Global Address List
• Search email for certain terms
• Find VPN info
• Reset 2FA keys or add new device
• Author(s)
• Beau Bullock (@dafthack)
• https://github.com/dafthack/MailSniper

7. OWA Attack Flow

8. Gaining A Foothold
Establishing Internal Network Access

9. Gaining A Foothold
• Phishing w/ PowerShell Payloads
• PowerShell Empire – PowerShell
agent with many capabilities
• Stagers/payloads, Lateral movement,
persistence, etc.
• Author(s): Will Schroeder (@harmj0y), Justin
Warner (@sixdub), & Matt Nelson (@enigma0x3)
• Unicorn – Generate PowerShell-
based payloads that inject
shellcode into memory
• Author(s): Dave Kennedy (@HackingDave)

10. Command and Control
Finding Holes in Egress Filtering

11. Command and Control
• Each of these can transfer files, establish shells, etc.
• Powercat - PowerShell version of Netcat
• Author(s): Mick Douglas (@besimorhino), Luke Baggett & Jesse Davis (@secabstraction)
• https://github.com/secabstraction/PowerCat
• Invoke-PowerShellIcmp – C2 channel over ICMP echoes and replies
• Author(s): Nikhil Mittal (@samratashok)
• https://github.com/samratashok/nishang/blob/master/Shells/Invoke-
PowerShellIcmp.ps1
• Dnscat2-PowerShell – C2 channel over DNS requests
• Author(s): Luke Baggett & dnscat2 server by Ron Bowes (@iagox86)
• https://github.com/lukebaggett/dnscat2-powershell

12. Situational Awareness
Perform Additional Reconnaissance As Silently As Possible

13. HostRecon
• Performs information gathering
about the local system, users and
domain
• Checks for common security
products
• Can check egress port filtering
• Doesn’t use any system
commands like ‘net’, ‘ipconfig’,
‘netstat’, ‘whoami’, etc.
• Author(s):
• Beau Bullock(@dafthack)
• https://github.com/dafthack/HostRecon

14. Privilege Escalation
Sometimes Admin Access Is Closer Than You Thought

15. PowerUp
• Performs a number of local
privilege escalation checks
• Checks for:
• Unquoted service paths
• Unattended Install Files
• Service Permissions
• …and more.
• Author(s):
• Will Schroeder (@harmj0y)
• https://github.com/PowerShellMafia/PowerSploit/tr
ee/master/Privesc

16. PowerUpSQL
• SQL server discovery
• Audit weak configurations
• Perform privilege escalation to
obtain SA privileges
• Find sensitive data at scale
• Author(s):
• Scott Sutherland (@_nullbind)
• https://github.com/NetSPI/PowerUpSQL

17. Domain Exploitation
Active Directory Fun Time

18. Invoke-Kerberoast
• Request TGS tickets (as any
domain user) for accounts with
SPNs set
• Extract the crackable hash
• Crack hashes offline
• Author(s):
• Will Schroeder (@harmj0y), Matan Hart
(@machosec), credit for original research to
Tim Medin (@timmedin)
• https://gist.github.com/HarmJ0y/cc1004307157e37
2fc5bd3f89e553059

19. Get-GPPPassword
• Finds any passwords of accounts
set by GPP
• Usually the first thing I check
• Almost always find an admin
password here
• Author(s):
• Chris Campbell (@obscuresec)
• https://github.com/PowerShellMafia/PowerSploit/b
lob/master/Exfiltration/Get-GPPPassword.ps1

20. BloodHound
• Enumerates/Gathers:
• Local admins group on all systems
• Active user sessions on each system
• Group membership information
• Domain trusts info
• Find a path to domain admin
• Authors(s):
• Andrew Robbins (@_wald0), Will Schroeder (@harmj0y),
and Rohan Vazarkar (@CptJesus)
• https://github.com/BloodHoundAD/BloodHound

22. PowerView
Find-LocalAdminAccess
• Find a system on the network your user is a local admin of
• Author(s): Will Schroeder (@harmj0y)
• https://github.com/PowerShellMafia/PowerSploit/blob/master/Recon/PowerView.ps1

23. DomainPasswordSpray
• Tool for password spraying all domain users
• Common Scenario:
• 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
• Author(s):
• Beau Bullock (@dafthack)
• https://github.com/dafthack/DomainPasswordSpray

25. Network Exploitation
Abusing Network Protocols and Finding Vulnerable Systems

26. Inveigh
• Exploit LLMNR & NBNS
• By default when DNS fails
Windows systems will query local
network
• Obtain NTLMv1/NTLMv2 hashes
• Crack hashes offline
• Author(s):
• Kevin Robertson (@kevin_robertson)
• https://github.com/Kevin-Robertson/Inveigh

27. PowerView
Get-ExploitableSystem
• Queries Active Directory for hostnames, OS versions, and service pack levels
• Cross-references those with common Metasploit modules
• Author(s):
• Scott Sutherland (@_nullbind), Will Schroeder (@harmj0y)
• https://github.com/PowerShellMafia/PowerSploit/blob/master/Recon/PowerView.ps1

28. PowerWebShot
• If escalation options are failing, might need to resort to network
attacks; Web servers tend to be good targets
• Default Creds
• Not patched internally
• etc…
• Analyze a large number of web servers quickly
• Inspiration and thanks goes to Chris Truncer for EyeWitness
• Author(s):
• Beau Bullock (@dafthack)

29. Post-Exploitation
Pillaging, Plundering, and Discovering Sensitive Data

30. Invoke-Mimikatz
• Dump cleartext credentials
• Avoids writing to disk
• Could sneakily dump creds from
LSASS dumps from other systems
• Author(s):
• Joe Bialek (@JosephBialek), & Benjamin
Delpy (@gentilkiwi)
• https://raw.githubusercontent.com/PowerShel
lMafia/PowerSploit/master/Exfiltration/Invoke
-Mimikatz.ps1

31. PowerView Invoke-ShareFinder /
Invoke-FileFinder
• Sensitive files on shares?
• 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*’
• Author(s):
• Will Schroeder (@harmj0y)

32. MailSniper
• Pillage sensitive data from every
user’s mailbox
• Gather credentials, insider intel,
network architecture info, etc.
• Search all mailboxes as admin or
current user’s as non-admin
• Author(s):
• Beau Bullock (@dafthack)
• https://github.com/dafthack/MailSniper

33. Obfuscating PowerShell
Making the Blue Team’s Life Hard

34. Invoke-Obfuscation
• Command line args are what
most monitoring tools alert on
when powershell.exe is run
• ‘LeT’+’s’+’ob’+’FusCa’+’te’
• Encode, concatenate, reorder,
etc.
• Author(s):
• Daniel Bohannon (@danielbohannon)
• https://github.com/danielbohannon/Invoke-
Obfuscation

35. PowerShell Without PowerShell
Oh, You Disabled PowerShell? We’ll See About That.

36. Using C#
• C# and PowerShell both are
basically frontends for the .NET
framework
• Can use csc.exe to compile C#
code containing ps1 script
• Results in standalone EXE
• Props to Brian Fehrman
(@fullmetalcache)
• http://www.blackhillsinfosec.com/?p=5257

37. PowerOps
• C# application that has many
PowerShell scripts built in
• PowerSploit
• Nishang
• GPPPassword
• Empire
• PowerCat
• …and more
• Author(s):
• Rui Reis (@fdiskyou)
• https://github.com/fdiskyou/PowerOPS

38. PowerLine / PowerStripper
• PowerStripper – preps ps1’s
for PowerLine, encodes, strips
comments
• PowerLine – purely run with
cmd-line args
• Works with Meterpreter and Empire
shells
• Author(s):
• Brian Fehrman (@fullmetalcache)
• https://github.com/fullmetalcache/PowerLine
• https://github.com/fullmetalcache/PowerStripp
er

39. Possible Mitigations
Ok, so how do I stop this madness?

40. Possible Mitigations
• Disable cmd.exe, PowerShell.exe, & PowerShell_ISE.exe for users
where possible
• Logging, monitoring, alerting
• Utilize enhanced logging in PowerShell v5.0
• Remove PSv2 to prevent logging bypass
• Use Sysmon to monitor and alert for system.management.automation DLL
• Ensure network and host-based IDS engines are tuned correctly
• Could possibly disable csc.exe compilation tool (be careful)
• Use AppWhitelisting (but know that there are still bypasses)

41. Conclusion
• PowerShell is… well…
Powerful
• Expect more tools to be
created
• Expect defenders to
implement more protections
• Expect attackers to find
bypasses for those
protections
Slide from Jeffrey “Father of PowerShell” Snover’s keynote at Derbycon 6.0

42. Questions?
• Black Hills Information Security
• http://www.blackhillsinfosec.com/
• @BHInfoSecurity
• Beau Bullock
• beau@blackhillsinfosec.com
• @dafthack