1. A Case Study
in Attacking
Keepass

2. @tifkin_
Red Teamer, Hunter, Capability Dev
UnmanagedPowerShell | RAT developer |
PowerShell Junkie

3. @harmj0y
Offensive Engineer and Red Teamer
Co-founder of Empire/EmPyre |
PowerTools | Veil-Framework
PowerSploit/BloodHound Developer

4. TL;DR
◈ KeePass Overview
◈ “Attacking” KeePass
⬥ KeePass.config.xml, key files, and more
⬥ Existing Work (KeeFarce)
⬥ KeeThief
⬥ The KeePass Trigger System
◈ Demos
◈ Mitigations

5. Our Big Point
If a password vault is unlocked, the key material
likely has to be somewhere in the process space,
so we can probably extract it.
But this doesn't mean you shouldn’t use a password
manager!!!
X

6. KeePass Overview
Architectural Background
and Offensive Motivations
1

7. KeePass
◈ A “free, open source, light-weight and
easy-to-use password manager”
⬥ 1.X is unmanaged C++ code
⬥ 2.X is C#/.NET
◈ Most commonly used password manager
we’ve seen in corporate environments
⬥ Self-contained/not hosted ‘in the cloud’

8. 2.X Key Material Options

9. KeePass Security Protections
◈ Strong Crypto
⬥ 6000 encryption rounds to prevent dictionary
attacks (though KeePass is now in HashCat ;)
◈ Secure Desktop
⬥ Similar to UAC, allows for the entering of a master
password on a different desktop to combat
keyloggers, but not enabled by default
◈ Process Memory Protection
⬥ RtlEncryptMemory/RtlDecryptMemory

10. KeePass and DPAPI
◈ The Data Protection API (DPAPI) is used to
encrypt key material for the ‘Windows User
Account’ setting
⬥ Mixes the current Windows user account in with
the master password/or keyfile to create a
composite master key
◈ The user’s DPAPI master key is used to
encrypt/decrypt a KeePass-specific ‘blob’

11. Recovering DPAPI Key Material: Restore-UserDPAPI.ps1

12. Process Memory Protection
◈ Sensitive data chunks (such as the master
password) are stored as encrypted blobs in
memory by using RtlEncryptMemory() and
RtlDecryptMemory()
◈ The “SameProcess” scope is set, so only the
KeePass process can decrypt the in-memory
strings!
⬥ Encryption keys are in kernel land

13. “Attacking” KeePass
KeePass.config.xml, key files, and more
2

14. Identifying KeePass
◈ If running:
⬥ Get-WmiObject win32_process | Where-Object
{$_.Name -like '*kee*'} | Select-Object -Expand
ExecutablePath
◈ If not:
⬥ Get-ChildItem -Path C:Users -Include
@("*kee*.exe", "*.kdb*") -Recurse -ErrorAction
SilentlyContinue | Select-Object -Expand FullName | fl
⬥ ls $env:APPDATAMicrosoftWindowsRecent |
?{$_.FullName -match 'kdb|keepass'}

15. Identifying KeePass

16. Cracking a KeePass Database
◈ HashCat 3.0.0 (released 6/29/16) now includes
support for KeePass 1.X and 2.X databases (-m
13400) thanks to @Fist0urs
⬥ keepass2john lets you extract a crackable hash (use
latest version for key file support)

17. KeePass.config.xml
◈ Located at
C:UsersuserAppDataRoamingKeePas
sKeePass.config.xml or in the folder of a
roaming installation
◈ The ‘KeySources’ section has some
interesting information...

18. KeePass.config.xml

19. Finding/Parsing KeePass.config.xml’s
◈ KeePassConfig.ps1 in KeeThief includes
Find-KeePassconfig:

20. Nabbing Key Files With WMI
◈ But what if key files are on a removable USB
drive?
◈ We drew inspiration from Matt Graeber’s
BlackHat 2015 “Abusing Windows
Management Instrumentation (WMI) to Build
a Persistent, Asynchronous, and Fileless
Backdoor” presentation

21. Nabbing Key Files With WMI
◈ The extrinsic WMI event
Win32_VolumeChangeEvent fires every
time a USB drive is inserted and mounted
◈ Non-reboot persistent option:
⬥ Register-WmiEvent -Query 'SELECT * FROM
Win32_VolumeChangeEvent WHERE EventType = 2'
-SourceIdentifier 'DriveInserted' -Action {$DriveLetter =
$EventArgs.NewEvent.DriveName;if (Test-Path
"$DriveLetterkey.jpg") {Copy-Item "$DriveLetterkey.jpg"
"C:Temp" -Force}}

22. New-WMIBackdoorAction Modification

23. Registering the Trigger
Register-WMIBackdoor -Trigger
$(New-WMIBackdoorTrigger
-DriveInsertion) -Action
$(New-WMIBackdoorAction
-FileClone)

24. Existing Work
(KeeFarce)
3

25. KeeFarce Release
◈ Released October 2015 by Denis Andzakovic
(denandz)
⬥ https://github.com/denandz/KeeFarce
◈ Allows for the export of an unlocked KeePass
database to a .CSV on disk!

26. “
“KeeFarce is
not a threat...”
-Dominik Reichl
(KeePass Author)
https://sourceforge.net/p/keepass/discussion/329220/thread/8e511d96/#e919

27. KeeFarce Process Part 1
1. Loads a malicious ‘bootstrap’ .DLL from disk
into KeePass using
VirtualAllocEx()/CreateRemoteThread() to
force a call LoadLibraryA()
2. The .DLL loads the .NET CLR and then loads
a custom .NET assembly from disk
3. The malicious assembly loads CLR MD and
attaches to the current KeePass.exe process

28. KeeFarce Process Part 2
4. Assembly uses CLR MD to walk the KeePass heap,
searching for KeePass.UI.DocumentManagerEx
objects
5. Loads the KeePass assembly with reflection and
instantiates a
KeePass.DataExchange.PwExportInfo object
6. KeePass.DataExchange.Formats.KeePassCsv1x is
instantiated, params set, and the export method
is invoked to export db to csv

29. KeeFarce Disadvantages
◈ In KeeFarce’s current state, the following
files have to be on disk:
⬥ BootstrapDLL.dll (.DLL that’s loaded),
KeeFarce.exe (launcher), KeeFarceDLL.dll
(malicious assembly),
Microsoft.Diagnostic.Runtime.dll (CLR MD)
◈ No PowerShell weaponization
◈ .NET 4+ (ClrMD)
◈ Only exports DB contents

30. KeeThief
Our Approach
4

31. KeeThief
◈ PowerShell 2.0-compatible tool to extract
the database key material from an opened
KeePass database
⬥ Uses a patched version of Microsoft’s CLR MD
⬥ Most of the work is in a C# assembly
⬥ Can be executed without a file touching disk!
◈ Also includes a patched KeePass version to
reuse the extracted key material

32. m_pbData:
Decryption key material
encrypted by
RtlEncryptMemory

33. 1. PowerShell script
loads a custom
.NET assembly
2. Custom assembly
loads .NET 2.0
backport of ClrMD
3. ClrMD locates
CompositeKey
object
4. ClrMD locates
references to
to key classes

34. 5. ClrMD locates and
extracts encrypted
key material
6. Assembly injects
shellcode to
decrypt key
material
7. Extracts plaintext
key material

36. The KeePass Trigger
System
Exfiltration Without Malware
….yes, really
5

37. KeePass’ Trigger System
◈ Version 2.X of KeePass has an available
event-condition-action trigger system
⬥ Specified in the
<TriggerSystem>...</TriggerSystem> section of
the active KeePass.config.xml, which is nearly
always modifiable
◈ We can use this to exfiltrate a database on
opening, or when specific entries are copied
to the clipboard!

38. KeePass’ Trigger System
◈ Interesting triggers:
⬥ Opened database file / Copied data to clipboard
◈ Interesting actions:
⬥ Export active database
⬦ Available “KeePass CSV (1.x)” format!
⬦ Accepts UNC paths as well as URLs!
⬥ Execute command line / URL
⬦ Invoke arbitrary .VBS/.PS1/etc.

42. .VBS Trigger

44. Auto-backdooring Triggers
◈ KeeThief’s KeePassConfig.ps1 also includes
Add-KeePassConfigTrigger to insert
malicious triggers into a KeePass.config.xml
◈ Find-KeePassconfig |
Add-KeePassConfigTrigger
⬥ -Action <X> : either ‘ExportDatabase’ or
‘ExfilDataCopied’

45. 7

46. Mitigations
All Is Not Lost
6

47. The Key Issue
◈ Ultimately, if a database is unlocked, the key
material likely has to be somewhere in the
process space, so we can probably extract it
◈ Current desktop OS architecture cannot
prevent this attack
◈ Can’t protect against features (triggers)

48. Detection/Things to beware of
◈ Host based monitoring (Sysmon,Carbon
Black, etc.)
⬥ Cross-process interaction (OpenProcess,
ReadProcessMemory, WriteProcessMemory,
CreateRemoteThread)
◈ PowerShell Module/Script Block Logging
◈ WMI Events
◈ Monitor changes to the KeePass config file
from non-KeePass processes

49. Thanks!
◈ Denis Andzakovic - Creator of KeeFarce
◈ Matt Graeber’s PIC_BindShell
⬥ Generating shellcode from C-code in Visual Studio
⬥ https://github.com/mattifestation/PIC_Bindshe
ll
◈ Microsoft’s ClrMD - .NET memory analysis
⬥ https://github.com/Microsoft/clrmd

50. Thanks!
Any questions?
@tifkin_ and @harmj0y
Get KeeThief:
https://github.com/HarmJ0y/KeeThief