Heartbreaker
Description
Delicate situation alert! The customer has just been alerted about concerning reports indicating a potential breach of their database, with information allegedly being circulated on the darknet market. As the Incident Responder, it's your responsibility to get to the bottom of it. Your task is to conduct an investigation into an email received by one of their employees, comprehending the implications, and uncovering any possible connections to the data breach. Focus on examining the artifacts provided by the customer to identify significant events that have occurred on the victim's workstation.
Files
We are given quite an extensive zip file. It contains fraction of Windows system files, with prefetches, logs, Events logs, user data, etc.
└─$ 7z x HeartBreaker.zip -P'hacktheblue'
Tasks
Task 1. The victim received an email from an unidentified sender. What email address was used for the suspicious email?
└─$ find . -iname '*mail*'
./wb-ws-01/C/Users/ash.williams/AppData/Local/Microsoft/Outlook/ashwilliams012100@gmail.com.ost
└─$ cd ./wb-ws-01/C/Users/ash.williams/AppData/Local/Microsoft/Outlook
└─$ file ashwilliams012100@gmail.com.ost
ashwilliams012100@gmail.com.ost: Microsoft Outlook Offline Storage (>=2003, Unicode, version 36), dwReserved1=0x78, dwReserved2=0x12ff86, bidUnused=0000000000000000, dwUnique=0x164f, 16818176 bytes, CRC32 0x28f18ca3
└─$ pffexport ashwilliams012100@gmail.com.ost # https://unix.stackexchange.com/a/611130
└─$ find . -empty -delete # Cleanup
└─$ tree -h -L 1
[4.0K] .
├── [4.0K] Contacts (This computer only)
├── [4.0K] [Gmail]
└── [4.0K] Inbox
4 directories, 0 files
After going through few mails in Inbox few can notice a suspicious email. Embedded file has double extension, is being served on IP rather then domain, port 9000 is also a bit sketchy and finally the sender pressures us to get it as soon as possible.

┌──(woyag㉿kraken)-[~/…/Outlook/ashwilliams012100@gmail.com.ost.export/Root - Mailbox/IPM_SUBTREE]
└─$ cat Inbox/Message00004/OutlookHeaders.txt
Message:
Client submit time: Mar 13, 2024 08:37:12.000000000 UTC
Delivery time: Mar 13, 2024 08:37:26.000000000 UTC
Creation time: Mar 13, 2024 10:43:24.699736200 UTC
Size: 690607
Flags: 0x00030011 (Read, Has attachments, Unknown: 0x00030000)
Conversation topic: Fingers crossed you'll notice..
Subject: Fingers crossed you'll notice..
Sender name: It's Me
Sender email address: ImSecretlyYours@proton.me
Sent representing name: It's Me
Sent representing email address: ImSecretlyYours@proton.me
Importance: Normal
Answer: ImSecretlyYours@proton.me
Task 2. It appears there's a link within the email. Can you provide the complete URL where the malicious binary file was hosted?
Answer: http://44.206.187.144:9000/Superstar_MemberCard.tiff.exe
Task 3. The threat actor managed to identify the victim's AWS credentials. From which file type did the threat actor extract these credentials?
From CTF challenges I participated the AWS key always started with AKIA after searching for it we end up on Draft email with Access keys!

The extension is .ost
because that's the file contents we are reading right now in verbose mode (like a zip file).
Answer: .ost
Task 4. Provide the actual IAM credentials of the victim found within the artifacts.
Answer: AKIA52GPOBQCK73P2PXL:OFqG/yLZYaudty0Rma6arxVuHFTGQuM6St8SWySj
Task 5. When (UTC) was the malicious binary activated on the victim's workstation?
For this type of information we can refer to Master File Table. Parse the MFT with MFTECmd
:
➜ .\MFTECmd\MFTECmd\bin\Debug\net6.0\MFTECmd.exe -f '.\$MFT' --csv . --csvf mft.csv
Created0x10: STANDARD_INFO created timestamp
Created0x30: FILE_NAME created timestamp [[Labs/HackTheBox/Sherlocks/DFIR/BFT/Writeup#Task 4. Analyze the $Created0x30 timestamp for the previously identified file. When was this file created on disk?|BFT Writeup]]

Usually the MFT holds the all information about file access, but the timestamps was not accepting. We can look info Prefetch file with PECmd
:
└─$ find . -iname '*tiff\.exe*'
./Windows/prefetch/SUPERSTAR_MEMBERCARD.TIFF.EXE-C2488B05.pf
---
➜ .\PECmd\PECmd\bin\Debug\net6.0\PECmd.exe -f .\SUPERSTAR_MEMBERCARD.TIFF.EXE-C2488B05.pf
PECmd version 1.5.0.0
Author: Eric Zimmerman (saericzimmerman@gmail.com)
https://github.com/EricZimmerman/PECmd
Command line: -f .\SUPERSTAR_MEMBERCARD.TIFF.EXE-C2488B05.pf
Keywords: temp, tmp
Processing .\SUPERSTAR_MEMBERCARD.TIFF.EXE-C2488B05.pf
Created on: 2024-07-04 19:52:05
Modified on: 2024-07-04 19:52:05
Last accessed on: 2024-07-04 19:52:48
Executable name: SUPERSTAR_MEMBERCARD.TIFF.EXE
Hash: C2488B05
File size (bytes): 244Â 988
Version: Windows 10 or Windows 11
Run count: 1
Last run: 2024-03-13 10:45:02
Volume information:
#0: Name: \VOLUME{01da694d2d1e2a56-562d2f1c} Serial: 562D2F1C Created: 2024-02-27 07:18:35 Directories: 114 File references: 1Â 635
Directories referenced: 114
Looks like the timestamp was 10 seconds off..
Answer: 2024-03-13 10:45:02
Task 6. Following the download and execution of the binary file, the victim attempted to search for specific keywords on the internet. What were those keywords?

└─$ find . -name '*History*'
./Users/svcaccount/AppData/Local/Microsoft/Edge/User Data/Default/History
./Users/svcaccount/AppData/Local/Microsoft/Edge/User Data/Default/History-journal
./Users/administrator/AppData/Local/Microsoft/Windows/History
./Users/ash.williams/AppData/Local/Microsoft/Edge/User Data/Default/History
./Users/ash.williams/AppData/Local/Microsoft/Edge/User Data/Default/History-journal
./Windows/System32/Tasks/Microsoft/Windows/FileHistory
./Windows/System32/Tasks/Microsoft/Windows/FileHistory/File History (maintenance mode)


└─$ find . -iname '*place*'
./Users/ash.williams/AppData/Roaming/Mozilla/Firefox/Profiles/hy42b1gc.default-release/places.sqlite
./Windows/System32/Tasks/Microsoft/Windows/Workplace Join
Looks like Firefox was used to download malware.


After malware download the user searched for Superstar cafe membership
Answer: Superstar cafe membership
Task 7. At what time (UTC) did the binary successfully send an identical malicious email from the victim's machine to all the contacts?
Searching for malware name we end up on Message00005
which contains all contacts that user had.


Mar 13, 2024 10:47:51.000000000 UTC
-> 2024-05-13 10:47:51
Answer: 2024-03-13 10:47:51
Task 8. How many recipients were targeted by the distribution of the said email excluding the victim's email account?
└─$ cat 'Users/ash.williams/AppData/Local/Microsoft/Outlook/ashwilliams012100@gmail.com.ost.export/Root - Mailbox/IPM_SUBTREE/[Gmail]/Sent Mail/Message00005/Recipients.txt' | grep Email | wc -l
59
Answer: 58
(-1 victim)
Task 9. Which legitimate program was utilized to obtain details regarding the domain controller?
The Windows Events Log should have what we are looking for, but there are too many.
└─$ find . -name '*.evtx' -print -quit
./Windows/System32/winevt/logs/Microsoft-Windows-Resource-Exhaustion-Detector%4Operational.evtx
┌──(woyag㉿kraken)-[~/…/Sherlock/Heartbreaker/wb-ws-01/C]
└─$ find . -name '*.evtx' | wc
113 129 9123
We can use Chainsaw to parse the events based on regex and find relevant info.
It was hard to filter all the events, so I focused on Event providers. Sysmon
is more precise event for this task.
➜ (.\chainsaw\chainsaw.exe search "Superstar_MemberCard.tiff.exe" .\logs -q | sls 'provider_' -Context 1,2 | findstr Name | group).name
Name: Microsoft-Windows-PowerShell
Name: Microsoft-Windows-Sysmon
Name: Microsoft-Windows-Windows Defender
Name: PowerShell
➜ .\chainsaw\chainsaw.exe search "Superstar_MemberCard.tiff.exe" .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q | sls 'TargetImage' | group | ft -Property Name
Name
----
TargetImage: C:\Program Files\Microsoft Office\Office16\OUTLOOK.EXE
TargetImage: C:\ProgramData\Microsoft\Windows Defender\Platform\4.18.24020.7-0\MsMpEng.exe
TargetImage: C:\Users\ash.williams\Downloads\Superstar_MemberCard.tiff.exe
TargetImage: C:\Users\Public\HelpDesk-Tools\WinSCP.com
TargetImage: C:\Windows\system32\gpresult.exe
TargetImage: C:\Windows\system32\nltest.exe
TargetImage: C:\Windows\System32\Wbem\WMIC.exe
You can use nltest.exe to:
Get a list of domain controllers
Force a remote shutdown
Query the status of trust
Test trust relationships and the state of domain controller replication in a Windows domain
Force a user-account database to synchronize on Windows NT version 4.0 or earlier domain controllers
➜ .\chainsaw\chainsaw.exe search -t 'Event.EventData.TargetImage: "*nltest.exe*"' .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q
---
Event:
EventData:
CallTrace: C:\Windows\SYSTEM32\ntdll.dll+9e664|C:\Windows\System32\KERNELBASE.dll+8e73|C:\Windows\System32\KERNELBASE.dll+71a6|C:\Windows\System32\KERNEL32.dll+1cbb4|C:\Windows\assembly\NativeImages_v4.0.30319_64\System\372e9962a41f186f070f1cb9f93273ee\System.ni.dll+384146|C:\Windows\assembly\NativeImages_v4.0.30319_64\System\372e9962a41f186f070f1cb9f93273ee\System.ni.dll+2c4809|C:\Windows\assembly\NativeImages_v4.0.30319_64\System\372e9962a41f186f070f1cb9f93273ee\System.ni.dll+2c4179|C:\Windows\assembly\NativeImages_v4.0.30319_64\System.Manaa57fc8cc#\31f3ff18d2438832c5c159e78f145c47\System.Management.Automation.ni.dll+111dec9|C:\Windows\assembly\NativeImages_v4.0.30319_64\System.Manaa57fc8cc#\31f3ff18d2438832c5c159e78f145c47\System.Management.Automation.ni.dll+10750ca|C:\Windows\assembly\NativeImages_v4.0.30319_64\System.Manaa57fc8cc#\31f3ff18d2438832c5c159e78f145c47\System.Management.Automation.ni.dll+10ff7bd|C:\Windows\assembly\NativeImages_v4.0.30319_64\System.Manaa57fc8cc#\31f3ff18d2438832c5c159e78f145c47\System.Management.Automation.ni.dll+10ff47b|C:\Windows\assembly\NativeImages_v4.0.30319_64\System.Manaa57fc8cc#\31f3ff18d2438832c5c159e78f145c47\System.Management.Automation.ni.dll+12028bf|UNKNOWN(00007FFC93466B41)
GrantedAccess: '0x1fffff'
RuleName: technique_id=T1055.001,technique_name=Dynamic-link Library Injection
SourceImage: C:\Users\ash.williams\Downloads\Superstar_MemberCard.tiff.exe
SourceProcessGUID: 8B118F18-83AE-65F1-8903-000000000900
SourceProcessId: 7252
SourceThreadId: 7312
SourceUser: WORK\ash.williams
TargetImage: C:\Windows\system32\nltest.exe
TargetProcessGUID: 8B118F18-83B3-65F1-8C03-000000000900
TargetProcessId: 7516
TargetUser: WORK\ash.williams
UtcTime: 2024-03-13 10:45:07.010
System:
Channel: Microsoft-Windows-Sysmon/Operational
Computer: wb-ws-01.work.com
Correlation: null
EventID: 10
EventRecordID: 5437
Execution_attributes:
ProcessID: 2352
ThreadID: 3188
Keywords: '0x8000000000000000'
Level: 4
Opcode: 0
Provider_attributes:
Guid: 5770385F-C22A-43E0-BF4C-06F5698FFBD9
Name: Microsoft-Windows-Sysmon
Security_attributes:
UserID: S-1-5-18
Task: 10
TimeCreated_attributes:
SystemTime: 2024-03-13T10:45:07.024319Z
Version: 3
Event_attributes:
xmlns: http://schemas.microsoft.com/win/2004/08/events/event
Answer: nltest.exe
Task 10. Specify the domain (including sub-domain if applicable) that was used to download the tool for exfiltration.
Sysmon > Event ID 22: DNSEvent (DNS query)
➜ .\chainsaw\chainsaw.exe search -t 'Event.System.EventID: =22' -t 'Event.EventData.Image: "*Superstar*"' .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q
---
Event:
EventData:
Image: C:\Users\ash.williams\Downloads\Superstar_MemberCard.tiff.exe
ProcessGuid: 8B118F18-83AE-65F1-8903-000000000900
ProcessId: 7252
QueryName: us.softradar.com
QueryResults: ::ffff:104.26.11.119;::ffff:172.67.69.160;::ffff:104.26.10.119;
QueryStatus: '0'
RuleName: '-'
User: WORK\ash.williams
UtcTime: 2024-03-13 10:45:20.904
System:
Channel: Microsoft-Windows-Sysmon/Operational
Computer: wb-ws-01.work.com
Correlation: null
EventID: 22
EventRecordID: 5495
Execution_attributes:
ProcessID: 2352
ThreadID: 3200
Keywords: '0x8000000000000000'
Level: 4
Opcode: 0
Provider_attributes:
Guid: 5770385F-C22A-43E0-BF4C-06F5698FFBD9
Name: Microsoft-Windows-Sysmon
Security_attributes:
UserID: S-1-5-18
Task: 22
TimeCreated_attributes:
SystemTime: 2024-03-13T10:45:23.285133Z
Version: 5
Event_attributes:
xmlns: http://schemas.microsoft.com/win/2004/08/events/event
Answer: us.softradar.com
Task 11. The threat actor attempted to conceal the tool to elude suspicion. Can you specify the name of the folder used to store and hide the file transfer program?
Sysmon > Event ID 11: FileCreate
➜ .\chainsaw\chainsaw.exe search -t 'Event.System.EventID: =11' -t 'Event.EventData.Image: "*Superstar*"' .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q | sls TargetFilenam
TargetFilename: C:\Users\ash.williams\AppData\Local\Temp\__PSScriptPolicyTest_urg0otbo.gwe.ps1
TargetFilename: C:\Users\ash.williams\Downloads\Superstar_MemberCard.tiff
TargetFilename: C:\Users\Public\Public Files
TargetFilename: C:\Users\Public\Public Files\username.txt
TargetFilename: C:\Users\Public\Public Files\DCinfo.txt
TargetFilename: C:\Users\Public\Public Files\localusers.txt
TargetFilename: C:\Users\Public\Public Files\AVinfo.txt
TargetFilename: C:\Users\Public\Public Files\UserProcesses.txt
TargetFilename: C:\Users\Public\Public Files\ashwilliams012100@gmail.com.ost
TargetFilename: C:\Users\Public\Public Files\Personal Requirements.docx
TargetFilename: C:\Users\Public\Public Files\Server_Inventory.xlsx
TargetFilename: C:\Users\Public\Public Files\Incident_Log.xls
TargetFilename: C:\Users\Public\Public Files\Incident_Report.pdf
TargetFilename: C:\Users\Public\Public Files\Configuration_Management.xlsx
TargetFilename: C:\Users\Public\Public Files\Performance_Metrics.xlsx
TargetFilename: C:\Users\Public\Public Files\Cloud_Architecture.pdf
TargetFilename: C:\Users\Public\Public Files\Deployment_Plan.docx
TargetFilename: C:\Users\ash.williams\AppData\Local\Temp\__PSScriptPolicyTest_pyju3jku.gc4.ps1
TargetFilename: C:\Users\Public\Public Files\Shareinfo.txt
TargetFilename: C:\Users\Public\Public Files\GPinfo.txt
TargetFilename: C:\Users\Public\Public Files\WB-WS-01.zip
TargetFilename: C:\Users\Public\Public Files\WinSCP.zip
TargetFilename: C:\Users\Public\HelpDesk-Tools
TargetFilename: C:\Users\Public\HelpDesk-Tools\license.txt
TargetFilename: C:\Users\Public\HelpDesk-Tools\readme.txt
TargetFilename: C:\Users\Public\HelpDesk-Tools\WinSCP.com
TargetFilename: C:\Users\Public\HelpDesk-Tools\WinSCP.exe
TargetFilename: C:\Users\Public\HelpDesk-Tools\maintenanceScript.txt
TargetFilename: C:\Users\Public\Public Files\Contacts.csv
WinSCP is an open source free SFTP client, FTP client, WebDAV client, S3 client and SCP client and file manager for Windows. Its main function is file transfer between a local and a remote computer. Beyond this, WinSCP offers scripting and basic file manager functionality
Answer: HelpDesk-Tools
Task 12. Under which MITRE ATT&CK technique does the action described in question #11 fall?
Easiest way if probably Google, lol D:

Masquerading fits the profile of attacker TTP.
Answer: Masquerading
Task 13: Can you determine the minimum number of files that were compressed before they were extracted?
➜ .\chainsaw\chainsaw.exe search -t 'Event.EventData.Image: "*Superstar*"' .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q | sls TargetFilename | sort | get-unique | sls files
TargetFilename: C:\Users\Public\Public Files
TargetFilename: C:\Users\Public\Public Files\ashwilliams012100@gmail.com.ost
TargetFilename: C:\Users\Public\Public Files\AVinfo.txt
TargetFilename: C:\Users\Public\Public Files\Change_Management_Policy.docx
TargetFilename: C:\Users\Public\Public Files\Cloud_Architecture.pdf
TargetFilename: C:\Users\Public\Public Files\Compliance_Checklist.pdf
TargetFilename: C:\Users\Public\Public Files\Configuration_Management.xlsx
TargetFilename: C:\Users\Public\Public Files\Contacts.csv
TargetFilename: C:\Users\Public\Public Files\Continuous_Integration_Strategy.docx
TargetFilename: C:\Users\Public\Public Files\DCinfo.txt
TargetFilename: C:\Users\Public\Public Files\Deployment_Plan.docx
TargetFilename: C:\Users\Public\Public Files\DevOps_Best_Practices.pdf
TargetFilename: C:\Users\Public\Public Files\Disaster_Recovery_Plan.docx
TargetFilename: C:\Users\Public\Public Files\GPinfo.txt
TargetFilename: C:\Users\Public\Public Files\Incident_Log.xls
TargetFilename: C:\Users\Public\Public Files\Incident_Report.pdf
TargetFilename: C:\Users\Public\Public Files\Incident_Response_Protocol.docx
TargetFilename: C:\Users\Public\Public Files\Infrastructure_Architecture.docx
TargetFilename: C:\Users\Public\Public Files\localusers.txt
TargetFilename: C:\Users\Public\Public Files\Network_Security_Policy.pdf
TargetFilename: C:\Users\Public\Public Files\Performance_Metrics.xlsx
TargetFilename: C:\Users\Public\Public Files\Personal Requirements.docx
TargetFilename: C:\Users\Public\Public Files\Server_Inventory.xlsx
TargetFilename: C:\Users\Public\Public Files\Service_Level_Agreement.docx
TargetFilename: C:\Users\Public\Public Files\Shareinfo.txt
TargetFilename: C:\Users\Public\Public Files\username.txt
TargetFilename: C:\Users\Public\Public Files\UserProcesses.txt
TargetFilename: C:\Users\Public\Public Files\WB-WS-01.zip
TargetFilename: C:\Users\Public\Public Files\WinSCP.zip
➜ .\chainsaw\chainsaw.exe search -t 'Event.EventData.Image: "*Superstar*"' .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q | sls TargetFilename | sort | get-unique | sls files | measure | ft -Property count
Count
-----
29
Public Files
directory, WB-WS-01.zip
and WinSCP.zip
can be excluded from the list as they are not relevant to exfiltration. 29 - 3 = 26 files exfiltrated from "Staging folder": Staging in this case means: the folder where the attacker works from.
Answer: 26
Task 14: To exfiltrate data from the victim's workstation, the binary executed a command. Can you provide the complete command used for this action?
➜ .\chainsaw\chainsaw.exe search -t 'Event.EventData.CommandLine: "*maintenanceScript.txt*"' .\logs\Microsoft-Windows-Sysmon%4Operational.evtx -q
---
Event:
EventData:
CommandLine: '"C:\Users\Public\HelpDesk-Tools\WinSCP.com" /script="C:\Users\Public\HelpDesk-Tools\maintenanceScript.txt" '
Company: Martin Prikryl
CurrentDirectory: C:\Users\ash.williams\Downloads\
Description: Console interface for WinSCP
FileVersion: 5.0.1.9730
Hashes: SHA1=224434759482423B3E3C75E06F6AB3A4FA193A33,MD5=F5AABAC14BE9EE43E22E840B6421938F,SHA256=BA7419F0AC2DFF1826217FABA581AF207F61A094144A4EBD381558BA38CC6601,IMPHASH=4930629D52BBA909DC99B790C62376E0
Image: C:\Users\Public\HelpDesk-Tools\WinSCP.com
IntegrityLevel: Medium
LogonGuid: 8B118F18-7F0A-65F1-0DDA-050000000000
LogonId: '0x5da0d'
OriginalFileName: winscp.com
ParentCommandLine: '"C:\Users\ash.williams\Downloads\Superstar_MemberCard.tiff.exe" '
ParentImage: C:\Users\ash.williams\Downloads\Superstar_MemberCard.tiff.exe
ParentProcessGuid: 8B118F18-83AE-65F1-8903-000000000900
ParentProcessId: 7252
ParentUser: WORK\ash.williams
ProcessGuid: 8B118F18-83C5-65F1-9103-000000000900
ProcessId: 7984
Product: WinSCP
RuleName: technique_id=T1083,technique_name=File and Directory Discovery
TerminalSessionId: 1
User: WORK\ash.williams
UtcTime: 2024-03-13 10:45:25.669
System:
Channel: Microsoft-Windows-Sysmon/Operational
...
Answer: "C:\Users\Public\HelpDesk-Tools\WinSCP.com" /script="C:\Users\Public\HelpDesk-Tools\maintenanceScript.txt"
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