I just solved Logging from Hack the Box!
Logging Machine Summary
Logging is a medium-difficulty Windows machine on Hack The Box that focuses on Active Directory enumeration, Kerberos authentication, certificate abuse, application exploitation, and privilege escalation through a rogue Windows Server Update Services (WSUS) infrastructure. The machine demonstrates how exposed log files, insecure Active Directory permissions, certificate-based authentication, and trust in internal update services can be chained together to achieve complete domain compromise.
The attack chain begins with Nmap enumeration, which identifies the target as an Active Directory Domain Controller exposing common domain services including DNS, Kerberos, LDAP, SMB, WinRM, and IIS. After performing host configuration and time synchronization to satisfy Kerberos authentication requirements, SMB share enumeration reveals an accessible Logs share containing several application log files.
Analysis of the downloaded logs uncovers hardcoded LDAP bind credentials belonging to the svc_recovery service account. After validating the credentials, Kerberos authentication is performed by requesting a Ticket Granting Ticket (TGT), followed by BloodHound enumeration of the Active Directory environment. BloodHound analysis reveals that svc_recovery possesses GenericWrite permissions over the msa_health$ machine account, providing a clear privilege escalation path through a Shadow Credentials attack.
Using Certipy, Shadow Credentials are added to the msa_health$ account, allowing certificate-based authentication and retrieval of the machine account's NTLM hash. The hash is then used to authenticate successfully through Evil-WinRM, establishing an initial foothold on the target system.
Following initial access, extensive post-exploitation enumeration is performed to understand the environment. User privileges, installed applications, scheduled tasks, directory structures, application binaries, and monitoring scripts are reviewed to identify potential privilege escalation opportunities. Application log enumeration and analysis reveal that the custom UpdateMonitor service repeatedly attempts to process a missing Settings_Update.zip archive and dynamically load settings_update.dll during scheduled update checks. Scheduled task enumeration confirms that the application executes automatically every few minutes under the jaylee.clifton user account.
Permission enumeration further reveals that authenticated users possess write access to the application's update directory, making the update mechanism vulnerable to DLL hijacking. A malicious DLL is generated using msfvenom, packaged into the expected ZIP archive, and delivered to the monitored directory. Once the scheduled task executes, the rogue DLL is loaded successfully, resulting in remote code execution and a reverse shell as jaylee.clifton. The user flag is subsequently retrieved from the compromised user's Desktop.
After obtaining user-level access, additional user directory enumeration uncovers an exported incident report describing a temporary migration to a staging WSUS server (wsus.logging.htb) alongside details of a continuously running synchronization task. These findings shift the focus toward the domain's internal software update infrastructure.
PowerShell is launched to perform certificate enumeration, where a user certificate is successfully requested using the Active Directory Certificate Services (AD CS) infrastructure. The certificate is exported as a password-protected PFX file, retrieved through Evil-WinRM, and reused locally for certificate-based authentication using Certipy. Active Directory Certificate Services enumeration identifies an enrollable certificate template suitable for abuse, allowing a new certificate to be requested for the staging WSUS server.
Using Kerberos-authenticated DNS management, a malicious DNS record is created that redirects wsus.logging.htb to the attacker's system. After verifying the DNS modification, the WSUS attack environment is prepared by installing and configuring the wsuks framework. A rogue WSUS server is then launched using the previously obtained certificate, allowing the attacker to impersonate the legitimate update server.
The rogue WSUS infrastructure is subsequently configured to deliver a malicious administrative command through the Windows Update mechanism. As the target performs its scheduled update synchronization, it downloads and executes the supplied payload, adding the previously compromised msa_health$ machine account to the local Administrators group.
Finally, administrative access is re-established through Evil-WinRM using the existing machine account credentials. Privilege verification confirms successful membership in the local Administrators group, enabling unrestricted access to the system. A recursive search locates the administrator's root.txt file, and reading the flag completes the machine with full system compromise.
Protected Page
The first step in owning the Logging machine like I have always done in my previous writeups is to connect my Kali Linux terminal with Hack the Box server. To establish this connection, I ran the following command in the terminal:
Once the connection between my Kali Linux terminal and Hack the Box server has been established, I started the Logging machine and I was assigned an IP address (10.129.40.175).
Nmap Enumeration
I began by performing a comprehensive Nmap scan against the target to identify open ports, running services, operating system details, and service versions. This initial enumeration provided a clear picture of the attack surface and immediately suggested that the target was a Windows Active Directory Domain Controller hosting the logging.htb domain.
The scan revealed several Active Directory-related services, including DNS (53), Kerberos (88), LDAP (389/636/3268/3269), SMB (445), RPC (135/593), and WinRM (5985), confirming that the host DC01 was the domain controller for logging.htb. In addition, IIS was running on port 80 with the default Windows Server page, while SMB signing was enforced, indicating that certain relay attacks would not be feasible. This information established the foundation for the next phase of enumeration, focusing on Active Directory and web service reconnaissance.
Host Configuration
After identifying the target as the logging.htb domain controller, I configured my local machine to resolve the domain name correctly. This allowed me to communicate with the target using its fully qualified domain name instead of the IP address, which is essential for many Active Directory services.
logging.htb and DC01.logging.htb to my /etc/hosts file, I ensured proper name resolution throughout the engagement. With the host configuration complete, I was ready to begin enumerating the domain services and web applications using their expected hostnames.Time Synchronization
Before interacting with the Active Directory environment, I synchronized my attack machine's clock with the target domain controller. Kerberos authentication is highly sensitive to time differences, so correcting the clock helps prevent authentication failures caused by clock skew.
SMB Share Enumeration
Using the provided domain credentials, I authenticated to the Logs SMB share and downloaded every available log file for offline analysis. Log files often contain valuable information such as usernames, service accounts, credentials, or configuration details that can be leveraged for further access.
Audit_Heartbeat.log, IdentitySync_Trace_20260219.log, Service_State.log, and TaskMonitor.log. These files became the next focus of my enumeration as they potentially contained sensitive operational information that could assist with privilege escalation or lateral movement.Log File Analysis
After downloading the log files from the SMB share, I began reviewing them to identify sensitive information that could aid further enumeration. The IdentitySync_Trace_20260219.log file immediately stood out because it contained detailed debugging information from an internal identity synchronization service.
LOGGING\svc_recovery along with its plaintext password Em3rg3ncyPa$$2025. The log also revealed that the account authenticated against DC01.logging.htb over LDAP, making these credentials an excellent candidate for validating access against the Active Directory domain.Credential Validation
After recovering the svc_recovery credentials from the log file, I attempted to authenticate to the SMB service to verify whether the account was valid and determine its level of access. This also allowed me to enumerate available SMB shares if the authentication succeeded.
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STATUS_ACCOUNT_RESTRICTION, indicating that the account was valid but restricted from interactive SMB logins. This suggested that svc_recovery was likely a service account, prompting me to test the credentials against other domain services that might permit authentication.Kerberos Authentication
Since the recovered service account was restricted from authenticating over SMB, I attempted to authenticate directly with Kerberos to verify whether the credentials were still valid. After successfully requesting a Ticket Granting Ticket (TGT), I configured my environment to use the cached Kerberos ticket for subsequent domain enumeration.
svc_recovery.ccache. I then exported the KRB5CCNAME environment variable so that Kerberos-aware tools would automatically use the cached ticket for authenticated interactions with the Active Directory domain, eliminating the need to repeatedly supply credentials.BloodHound Enumeration
With valid domain credentials, I ran BloodHound to enumerate the Active Directory environment and collect information about users, groups, computers, Group Policy Objects, and privilege relationships. This provided a complete dataset for identifying potential attack paths and privilege escalation opportunities.
20260627203526_bloodhound.zip, which I imported into the BloodHound interface to visually analyze privilege relationships and identify the next attack path.BloodHound Analysis
After importing the BloodHound collection into the interface, I analyzed the relationships between the recovered accounts to identify potential privilege escalation paths. The graph revealed a clear attack chain that was not immediately obvious from standard Active Directory enumeration.
The BloodHound analysis showed that the svc_recovery account possessed GenericWrite permissions over the msa_health$ managed service account. In addition, msa_health$ had CanPSRemote rights on DC01.logging.htb, indicating that it was permitted to establish remote PowerShell sessions to the domain controller. This combination identified a viable privilege escalation path, where gaining control of msa_health$ could ultimately provide remote administrative access to DC01.
Shadow Credentials Attack
After confirming in BloodHound that svc_recovery had GenericWrite permissions over the msa_health$ account, I abused this privilege using Certipy's Shadow Credentials attack. This technique temporarily added a Key Credential to the target account, allowing me to authenticate as msa_health$ without knowing its password.
msa_health$, and extracting its NTLM hash. Certipy then automatically restored the original Key Credentials, leaving the account unchanged while providing me with the NTLM hash 603fc24ee01a9409f83c9d1d701485c5, which I used for the next stage of the attack.Remote Access with Evil-WinRM
After obtaining the NTLM hash for the msa_health$ managed service account, I authenticated to the target over WinRM using a pass-the-hash attack. Since BloodHound had previously shown that this account had CanPSRemote rights on the domain controller, I expected it to permit remote PowerShell access.
msa_health$ on DC01. This provided me with an interactive shell on the domain controller, allowing me to begin post-exploitation enumeration and search for opportunities to escalate privileges further.Post-Exploitation Enumeration
After gaining a remote PowerShell session as msa_health$, I enumerated the user's home directory to identify any scripts or files that could reveal how the account was being used. A PowerShell script named monitor.ps1 immediately stood out, so I examined its contents for additional clues.
C:\Share\Logs\TaskMonitor.log. This revealed that the account was responsible for monitoring scheduled tasks and identified both the task name and log location, providing valuable information for the next stage of privilege escalation.Privilege Enumeration
After establishing a foothold on the domain controller, I enumerated the security context of the msa_health$ account to determine its group memberships and assigned privileges. This helped me understand what actions the account was permitted to perform and identify potential privilege escalation opportunities.
logging\msa_health$ managed service account, which belonged to the Domain Computers and Remote Management Users groups. Although the account had only a few default privileges, the enabled SeMachineAccountPrivilege stood out because it allows the creation of computer accounts in the domain, making it a potential avenue for further Active Directory privilege escalation.Application Enumeration
After inspecting the monitoring script, I enumerated the installation directory of the application it referenced to better understand its components and dependencies. Examining the application's files could reveal configuration files, third-party libraries, or executables that might be vulnerable or misconfigured.
UpdateMonitor.exe along with its configuration files and a packages directory containing the System.IO.Compression.ZipFile .NET library. This indicated that the application was a custom .NET program packaged with its dependencies, making UpdateMonitor.exe the primary target for further reverse engineering and analysis in search of privilege escalation opportunities.Application Log Enumeration
After identifying the application's installation directory, I searched for its runtime data to locate log files that might reveal how the application operated. Application logs often contain execution details, errors, or references to scheduled tasks that can assist with further analysis.
Logs directory containing a single monitor.log file. Since this log was actively updated and significantly larger than the other files, it became the next target for analysis, as it was likely to contain valuable runtime information about the UpdateMonitor application and its scheduled execution.Application Log Analysis
After locating the application's log file, I examined the most recent entries to understand how the update mechanism operated and identify any weaknesses. Reviewing the latest log entries often reveals missing files, failed components, or execution paths that can be abused.
UpdateMonitor periodically checked both a core server and the local system for Settings_Update.zip before attempting to load settings_update.dll from C:\Program Files\UpdateMonitor\bin\. Each execution failed with Error 126, indicating the DLL could not be loaded. This behavior exposed the application's update workflow and suggested that the missing DLL and update package could become the focus of the next privilege escalation step.Scheduled Task Enumeration
After understanding how the update application operated, I inspected the scheduled task responsible for launching it. Examining the task definition allowed me to determine how frequently it executed, which user account ran it, and the exact command being invoked.
UpdateMonitor.exe every three minutes under the domain user LOGGING\jaylee.clifton. It also revealed the command-line arguments passed to the application (500 /scan=3 /autofix=true), confirming that the update process was automated. This information identified the execution context of the application and provided valuable insight for investigating potential privilege escalation opportunities through the scheduled update mechanism.Directory Enumeration
After identifying the scheduled task and the executable it launched, I enumerated the application's installation directory to verify its contents and determine whether any additional binaries or configuration files were present. This also helped confirm the location of the executable referenced by the scheduled task.
UpdateMonitor.exe, two configuration files, and the bin and packages directories used by the application. This confirmed that UpdateMonitor.exe was the only executable in the installation path, making it the primary target for further analysis and investigation of the application's update mechanism.Binary Extraction
After identifying UpdateMonitor.exe as the application executed by the scheduled task, I downloaded a local copy from the target system for offline analysis. Analyzing the binary on my attack machine would allow me to inspect its functionality without interacting directly with the target.
Application Log Review
After downloading the binary, I reviewed the complete application log to better understand the update process and determine whether the observed behavior was consistent over time. Analyzing the full log helped me identify how the application searched for updates and where the process repeatedly failed.
Settings_Update.zip on both a core server and the local system before attempting to load settings_update.dll from C:\Program Files\UpdateMonitor\bin\. Every execution failed with Error 126, indicating that the DLL was missing or could not be loaded. This repeated failure exposed a predictable update workflow, making the application's DLL loading mechanism the primary focus for the next privilege escalation step.Permission Enumeration
After understanding how the update process worked, I checked the permissions on the application's data directory to determine whether my current account could modify any files used during the update routine. Writable directories used by privileged applications are often a valuable privilege escalation vector.
SYSTEM and Administrators had full control, the BUILTIN\Users group also had Write Data, Append Data, and Write Extended Attributes permissions. Since the update process searched this directory for Settings_Update.zip, these permissions suggested that a low-privileged user could place files in the update location, making the application's update mechanism a promising target for further exploitation.Payload Preparation
After discovering that the update process searched for Settings_Update.zip and attempted to load settings_update.dll, I prepared a replacement DLL for the application's update mechanism. I then packaged the DLL into a ZIP archive using the expected filename so it would match the format referenced by the update process.
Settings_Update.zip, matching the filename expected by the application's update routine. With the archive prepared, I was ready to test whether the automated update mechanism would process the package during its next scheduled execution.Gaining Code Execution
After preparing the update package, I started a Netcat listener to receive an incoming connection and hosted the ZIP archive on a temporary HTTP server. From my existing Evil-WinRM session, I downloaded the update package into the location monitored by the application's update process.
On the Evil-WinRM shell, I ran the command:
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A few moments later, the scheduled UpdateChecker Agent detected the newly uploaded archive, processed the update, and established a reverse shell back to my Netcat listener. The connection returned an interactive Windows command prompt from the target system, confirming successful code execution through the application's automated update mechanism.
User Flag
After receiving the reverse shell, I verified the security context of the compromised process to determine which account the scheduled update mechanism was running under. Once I confirmed the user context, I navigated to the user's Desktop and retrieved the user flag.
whoami command confirmed that the reverse shell was executing as logging\jaylee.clifton, the same account configured to run the UpdateChecker Agent scheduled task. I then navigated to the user's Desktop, verified that user.txt was present, and displayed its contents, successfully obtaining the user flag and confirming user-level access on the target system.User Directory Enumeration
After obtaining the user flag, I continued enumerating the compromised user's profile to search for additional artifacts that could assist with privilege escalation. I navigated through the Documents directory and discovered a folder named Tickets, which appeared to contain support or administrative documentation.
Tickets directory, I found a single HTML file named Incident_4922_WSUS_Remediation_ViewExport.html. Based on its name, the file appeared to be an exported incident report related to WSUS remediation, making it a promising source of information for identifying administrative procedures or misconfigurations that could lead to further privilege escalation.Incident Report Analysis
After discovering the exported support ticket, I examined its contents to identify any operational details that could reveal additional attack vectors. Administrative documentation often contains internal hostnames, scheduled tasks, or infrastructure changes that are not exposed through standard enumeration.
wsus.logging.htb because of issues with the production update infrastructure. It also disclosed the existence of a scheduled ForceSync task running every 120 seconds to reset the Windows Update components. These findings pointed to a custom WSUS deployment and an automated synchronization process, providing valuable clues for the next stage of privilege escalation.Host Configuration
After discovering the internal WSUS hostname in the incident report, I updated my local hosts file so my attack machine could resolve it correctly. This ensured that any tools or browsers referencing the WSUS server would connect to the target using its expected hostname.
wsus.logging.htb to the target IP address, I enabled proper hostname resolution for the staging WSUS server described in the support ticket. With the host configuration complete, I was ready to begin enumerating the WSUS service and investigate whether it could be leveraged for privilege escalation.PowerShell Session
Before continuing with the WSUS investigation, I verified the default command interpreter available to my current session and switched from the Command Prompt to Windows PowerShell. PowerShell provides more powerful cmdlets and is better suited for system administration and Active Directory enumeration.
%COMSPEC% environment variable confirmed that the default shell was C:\Windows\System32\cmd.exe. I then launched a PowerShell session successfully, giving me access to native PowerShell cmdlets and a more flexible environment for the remaining stages of post-exploitation and privilege escalation.Certificate Enumeration
After switching to PowerShell, I began enumerating the current user's certificate store to determine whether I could request or use client certificates for authentication. I also prepared a secure password that would later be used to protect an exported certificate.
My) store was initially empty. I then requested a new certificate using the User certificate template and stored the resulting certificate object in the $cert variable. Finally, I created a secure string containing the export password, which would be used when exporting the certificate for later authentication.Certificate Export
After successfully requesting a user certificate, I created a temporary directory to store it and exported the certificate in PFX format. Exporting the certificate with its private key allowed me to reuse it later for certificate-based authentication.
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C:\tmp\jaylee.pfx in the temporary directory. I then verified that the file existed, confirming that the certificate and its associated private key had been exported correctly and were ready for use in the next stage of the attack.Certificate Retrieval
After exporting the user certificate to the temporary directory, I switched back to my Evil-WinRM session to retrieve a copy onto my attack machine. Downloading the certificate locally allowed me to use it for certificate-based authentication outside the target environment.
jaylee.pfx was present in the temporary directory before downloading it through Evil-WinRM. The transfer completed successfully, giving me a local copy of the exported certificate and private key for use in the next stage of the privilege escalation process.Certificate-Based Authentication
After downloading the exported certificate, I authenticated to the Active Directory domain using certificate-based authentication with Certipy. This allowed me to obtain Kerberos credentials for the compromised user without relying on a password.
jaylee.clifton@logging.htb. Certipy obtained a Kerberos TGT, saved it as jaylee.clifton.ccache, and recovered the user's NTLM hash. With both the Kerberos ticket and NTLM hash available, I had multiple authentication options for the remaining stages of the attack.Active Directory Certificate Services Enumeration
After authenticating as jaylee.clifton, I configured my Kerberos ticket and enumerated the Active Directory Certificate Services (AD CS) environment using Certipy. This allowed me to identify available Certificate Authorities, enabled certificate templates, and any potential certificate-based privilege escalation paths.
The enumeration revealed a single Enterprise CA (logging-DC01-CA) with several enabled certificate templates. Among the results, I identified that the Machine template was enrollable by Domain Computers and marked as a potential ESC2/ESC3 target, indicating a possible path for certificate abuse. This information helped narrow the attack surface and guided the next phase of privilege escalation through Active Directory Certificate Services.
AD CS Certificate Request
After identifying an enrollable certificate template, I requested a certificate from the Enterprise CA using the UpdateSrv template. I specified the wsus.logging.htb hostname as both the UPN and DNS name, then converted the issued certificate into PEM format for compatibility with other authentication tools.
DNS Record Manipulation
After obtaining Kerberos authentication as jaylee.clifton, I used the Kerberos ticket to add a new DNS record for the wsus hostname. This redirected wsus.logging.htb to my attack machine, allowing me to intercept future connections intended for the staging WSUS server.
wsus DNS record had been created and now resolved to my attacker IP address. I also verified that the Kerberos credential cache was present and available for authentication. With DNS successfully redirected, I was positioned to capture and service connections destined for wsus.logging.htb during the next phase of the attack.DNS Record Verification
After creating the malicious DNS record, I verified that the change had been successfully applied in Active Directory. Confirming the record ensured that any requests for wsus.logging.htb would now resolve to my attacker-controlled system.
wsus.logging.htb had been successfully added to the DNS zone and now resolved to my VPN IP address (10.10.15.28). Verifying the record ensured that subsequent connections to the WSUS server would be redirected to my machine, allowing me to intercept and interact with the target's update traffic during the next stage of the attack.WSUS Server Setup
After redirecting the WSUS hostname to my attacker machine, I installed the wsuks tool and verified that it had been added to my local environment. I then attempted to start the rogue WSUS server using the certificate I had previously obtained.
which wsuks confirmed that the binary was installed under my local user directory. However, the final command failed with sudo: wsuks: command not found because sudo did not inherit my user's PATH, preventing it from locating the executable. This indicated that I needed to either execute wsuks using its full path or preserve my environment before continuing with the rogue WSUS server setup.WSUS Environment Preparation
After discovering that sudo could not locate the wsuks executable, I reinstalled the tool with access to the system site packages to resolve the dependency issue. I then verified that the required Python modules were available before proceeding with the rogue WSUS server setup.
ok, confirming that the required nftables dependency was available inside the wsuks virtual environment. With the installation issue resolved, my environment was fully prepared to launch the rogue WSUS server in the next stage of the attack.Rogue WSUS Server
After preparing my environment and obtaining a valid certificate for the WSUS server, I launched the rogue WSUS service to impersonate the legitimate update server. This allowed me to intercept update requests from the target and serve a malicious update payload.
KB2990974) for delivery, confirming that my rogue WSUS infrastructure was ready to service incoming update requests from the compromised host.WSUS Command Execution
After confirming that the rogue WSUS server was operational, I restarted it with a custom command that would execute when the target retrieved the malicious update. I configured the server to deliver the payload while listening on my VPN interface and waited for the scheduled WSUS client to connect.
PsExec64.exe demonstrated that the update workflow was being executed, indicating that my supplied command had been delivered through the spoofed WSUS infrastructure.Administrative Access
After the rogue WSUS server delivered the command successfully, I reconnected to the target using the previously recovered NTLM hash for the msa_health$ account. This allowed me to verify whether the account had been successfully added to the local Administrators group.
msa_health$. Since the WSUS-delivered command had already modified the account's local group membership, this new session now reflected the elevated privileges, providing the administrative access required to continue with the final stage of privilege escalation.Privilege Verification
After reconnecting to the target, I verified that the WSUS-delivered command had completed successfully by checking the membership of the local Administrators group. This confirmed whether the msa_health$ account had received administrative privileges on the system.
msa_health$ had been added to the local Administrators group alongside the built-in Administrator, Domain Admins, and Enterprise Admins. This confirmed that the privilege escalation had succeeded, granting my compromised service account full administrative access to the target and paving the way for obtaining the root flag.Root Flag Enumeration
After confirming that my account had administrative privileges, I searched the entire C: drive for the root flag. Rather than manually browsing user profiles, I recursively enumerated the filesystem to quickly locate every instance of root.txt.
root.txt on toby.brynleigh's Desktop, confirming that I now had sufficient privileges to access the administrator's profile. With the flag's location identified, the final step was simply to read its contents and complete the machine.Root Flag
After locating the administrator's Desktop, I accessed the root.txt file to verify that the privilege escalation was successful. Reading the flag confirmed that I had achieved full administrative control over the target system.
root.txt, confirming successful retrieval of the root flag. With both the user and root flags collected, I had successfully completed the machine by chaining Active Directory misconfigurations, application abuse, and a rogue WSUS update process to obtain full system compromise.Keywords:
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