Just finished the Insane difficulty Eloquia machine on Hack The Box which one of the more layered and creative Windows boxes I’ve done in a while.

The path starts with a custom Django publishing platform that integrates with a Qoogle OAuth service. After registering and creating articles, you discover that the application trusts certain meta-refresh tags and can be leveraged for redirects. Combined with OAuth authorization flows and a bit of CSRF, this opens the door to higher-privilege access inside the web application.

From the admin interface, SQL Explorer becomes available. Because the backend is SQLite, `load_extension` can be abused to load a malicious DLL. That gives the first reverse shell as the `eloquia\web` user and the user flag.

Privilege escalation requires deeper enumeration. Edge browser credentials stored for the Olivia.KAT account can be extracted and decrypted offline. WinRM then provides a stable shell as that user. From there, Seatbelt and process enumeration reveal an interesting custom service called Failure2Ban that runs with high privileges and periodically restarts. By racing a binary overwrite of `Failure2Ban.exe` with a reverse shell, you land as `NT AUTHORITY\SYSTEM` and grab the root flag.

What made this machine feel genuinely Insane was the number of different skill sets required: web application logic, OAuth/CSRF, SQLite extension loading, Windows credential dumping, service abuse under AppLocker and PowerShell restrictions, and careful timing for the final binary overwrite.

Great learning experience overall.

#HackTheBox #CTF #PenetrationTesting #WindowsPrivilegeEscalation #RedTeam #InfoSec #Eloquia #InsaneBox …

Learn MoreHack The Box: Eloquia Machine Walkthrough – Insane Difficulty

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Completed another Hack The Box machine: Devhub (Medium).

Devhub was a great exercise in exploring modern development tooling, service misconfigurations, and Linux privilege escalation. The journey began with web enumeration and identifying an exposed MCP Inspector service. Further investigation revealed a command injection vulnerability that provided initial access to the machine.

From there, internal service enumeration uncovered a localhost-only Jupyter instance. Accessing it through SSH port forwarding and investigating its authentication mechanism opened the path to another user. The final stage involved examining an internal operations service, understanding its exposed functionality, and identifying a weakness that ultimately led to root access.

Devhub highlights how development tools, internal services, and poorly secured administrative functionality can create unexpected attack paths when combined. Another valuable machine for practising enumeration, lateral movement between local users, and privilege escalation.

#HackTheBox #HTB #CyberSecurity #PenetrationTesting #RedTeam #OffensiveSecurity #Linux #PrivilegeEscalation #WebSecurity #MCP #InfoSec …

Learn MoreHack The Box: Devhub Machine Walkthrough – Medium Difficulty

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Completed another Hack The Box machine: Hercules, an Insane difficulty Active Directory challenge.

This was one of the longer attack chains I have worked through, involving multiple stages across web exploitation, credential access, Active Directory enumeration, privilege escalation, AD CS, and Kerberos abuse.

The initial foothold started with LDAP username enumeration and the discovery of credentials stored in an account description. After gaining access to the Hercules Portal, a directory traversal vulnerability exposed the web.config file and its ASP.NET machineKey values. These values allowed a forged Forms Authentication cookie to impersonate web_admin.

From there, a malicious ODT upload triggered an outbound NTLM authentication attempt, allowing the NetNTLMv2 credentials for natalie.a to be captured and cracked. The recovered credentials opened the path to Shadow Credentials against bob.w and stephen.m, followed by OU permission abuse to gain control of the Auditor account.

The privilege escalation chain continued through the Forest Migration OU, where fernando.r was enabled and used to identify an ESC3 misconfiguration. An Enrollment Agent certificate was then obtained and abused to request a certificate for ashley.b, leading to further access within the domain.

The final stages involved controlling IIS_Administrator, taking control of the iis_webserver$ machine account, extracting the required Kerberos session key, and abusing S4U2self/S4U2proxy to impersonate Administrator. This ultimately provided access to the root flag under C:\Users\Admin\Desktop.

Hercules was a great exercise in chaining several seemingly separate weaknesses together rather than relying on a single vulnerability. Definitely a box that required careful enumeration and keeping track of the relationships between users, groups, OUs, certificates, and Kerberos tickets.

Documented as part of my continued HTB practice and learning in Active Directory and offensive security.

#HackTheBox #HTB #Hercules #CyberSecurity #ActiveDirectory #PenetrationTesting #RedTeam #OffensiveSecurity #BloodHound #Certipy #ADCS #ESC3 #Kerberos #ShadowCredentials #PrivilegeEscalation #InfoSec #CyberSecurityLearning …

Learn MoreHack The Box: Hercules Machine Walkthrough – Insane Diffucility

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Completed the Hack The Box “CobbleStone” Insane machine, chaining multiple vulnerabilities to achieve full system compromise.

Initial access was achieved through SSRF in the skin suggestion feature, followed by SQL injection and stored XSS to compromise the administrator’s session. The stolen session cookie provided admin access, leading to Twig SSTI and RCE as www-data. Database credentials recovered through SSTI enabled a database dump and password cracking, resulting in SSH access as cobble and the user flag.

Local enumeration revealed Cobbler’s XML-RPC service on port 25151. After identifying Cobbler 3.3.6 as vulnerable to CVE-2024-47533, a malicious Cheetah template was used to execute commands with root privileges. This provided a root shell and access to /root/root.txt.

#HackTheBox #HTB #CobbleStone #CyberSecurity #PenetrationTesting #OffensiveSecurity #WebSecurity #SSRF #SQLInjection #XSS #SSTI #PrivilegeEscalation #CVE-2024-47533 …

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Completed the Hack The Box "Kobold" machine, an easy-difficulty Linux challenge focused on web exploitation and container-based privilege escalation.

The assessment involved identifying and exploiting an unauthenticated Remote Code Execution vulnerability (CVE-2026-23744) in MCPJam Inspector to gain initial access as the ben user. During the privilege escalation phase, I explored Docker security weaknesses by leveraging excessive group permissions to escape the container environment and obtain root access. Additionally, I analyzed an alternative attack path involving CVE-2025-64714 in PrivateBin, which allowed sensitive configuration data exposure and access to the Arcane container management interface. This machine provided practical experience in vulnerability exploitation, container security assessment, and identifying risks associated with exposed internal services.

#HackTheBox #HTB #CyberSecurity #PenetrationTesting #OffensiveSecurity #RedTeam #Linux #Docker #VulnerabilityManagement #CVE #EthicalHacking #CybersecurityLearning …

Learn MoreHack The Box: Kobold Machine Walkthrough – Easy Difficulty

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Just completed the DevArea machine from Hack The Box!

After exploiting a vulnerable Java SOAP service on port 8080, I gained initial access and discovered Hoverfly running on port 8888. Leveraging CVE-2025-54123, I successfully authenticated and delivered a reverse shell, securing the User flag as the dev_ryan user.

For privilege escalation, I took advantage of a sudo permission on the SysWatch management script. By exploiting a symlink attack in the logging functionality, I was able to read /root/root.txt and capture the Root flag.

Really enjoyed this Medium-difficulty box — great mix of Java deserialization/SOAP, API exploitation, and creative Linux privilege escalation!

#HackTheBox #HTB #PenetrationTesting #CyberSecurity #PrivilegeEscalation #CVE #EthicalHacking …

Learn MoreHack The Box: DevArea Machine Walkthrough – Medium Difficulty

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