Insane Machine Archives - Threatninja.net

17 Oct, 2026

Hack The Box: Eloquia Machine Walkthrough – Insane Difficulty

Insane Machine Challenges, csrf, Decryptor, DLL Hijacking, Failure2Ban, HackTheBox, Linux, Oauth, Penetration Testing, python3, responsder, sql database, ssh

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

19 Sep, 2026

Hack The Box: Hercules Machine Walkthrough – Insane Diffucility

Insane Machine Bloodhound, bloodyAD, BurpSuite, Certipy, Challenges, changepassword.py, describeticket.py, dotnet, getTGT, HackTheBox, hashcat, impacket-getST, kerbrute, LDAP, odt, Penetration Testing, PowerView, python3, responder, SSO Authentication, Windows, winrmexec

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

15 Aug, 2026

HackTheBox: CobbleStone Machine Walkthrough – Insane Difficulty

Insane Machine BurpSuite, Challenges, Cobbler’s XML-RPC, CVE-2024-47533, gobuster, HackTheBox, hashcat, Linux, MySQL, mysql database, Penetration Testing, port forwarding, python3, SQL Injection, ssh, ssrf, Stored XSS, Twig SSTI

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 …

Learn MoreHackTheBox: CobbleStone Machine Walkthrough – Insane Difficulty

25 Apr, 2026

Hack The Box: Sorcery Machine Walkthrough – Insane Difficulty

Insane Machine BurpSuite, Challenges, Cypher Injection, docker, Gitea, HackTheBox, hashcat, ipa, Ligolo-ng, Linux, pem2john, Penetration Testing, pspy64, ssh, WebAuthn

Recently, I completed the “Sorcery” machine on Hack The Box (Insane difficulty), which provided a deep, multi-layered challenge combining modern web exploitation, internal pivoting, and complex privilege escalation.

The attack began with reconnaissance of a self-hosted Gitea instance, where exposed source code revealed the application architecture. This led to identifying a Cypher injection vulnerability in functionality backed by Neo4j, which enabled SSRF to leak sensitive data such as password hashes and a registration key. After gaining seller access, a stored XSS payload was used to hijack an admin session and access a restricted debug feature. This interface allowed interaction with internal services, ultimately achieving remote code execution via a Kafka-based payload. From there, pivoting with Ligolo-ng exposed internal services, including an FTP server containing an encrypted private key, which was cracked offline to gain SSH access and retrieve the user flag.

Privilege escalation required chaining multiple subtle misconfigurations. A running Xvfb instance exposed a screen dump containing credentials for a higher-privileged user. With limited sudo access, strace was used to capture plaintext credentials from running processes. Further enumeration revealed activity tied to FreeIPA, where identity management controls were abused to gain full sudo privileges. After applying the changes, this ultimately led to root access and full system compromise.

#HackTheBox #CyberSecurity #PenetrationTesting #RedTeam #EthicalHacking #CTF #Infosec #PrivilegeEscalation #WebSecurity …

Learn MoreHack The Box: Sorcery Machine Walkthrough – Insane Difficulty

13 Dec, 2025

Hack The Box: WhiteRabbit Machine Walkthough – Insane Difficulity

Insane Machine 7zip, Authentication Bypass, BurpSuite, Challenges, ffuf, ghidra, gobuster, HackTheBox, Linux, n8n, neo-password-generator, Penetration Testing, python3, restic, SQL Injection, ssh, Uptime Kuma, webhook

Initial access was achieved through exposed monitoring and documentation services, which leaked internal service names and an unauthenticated workflow configuration. This disclosure revealed sensitive secrets, a vulnerable webhook parameter, and ultimately credentials for a backup system. Abuse of misconfigured backup tooling and sudo privileges allowed extraction of private SSH keys, enabling lateral movement across multiple user accounts and retrieval of the user flag.

Privilege escalation to root involved reverse-engineering a custom SUID binary. Analysis exposed a predictable pseudorandom password generator caused by unsafe seeding logic and an integer overflow, significantly reducing entropy. Recreating the binary locally and brute-forcing the constrained seed space yielded valid credentials, granting SSH access to a privileged user with unrestricted sudo rights and full system compromise.

This machine was a strong example of how exposed internal tooling, poor secret handling, and flawed custom binaries can combine into a complete attack chain.

#HackTheBox #CyberSecurity #OffensiveSecurity #PenetrationTesting #RedTeam #PrivilegeEscalation #ReverseEngineering #LinuxSecurity #Infosec #CTF …

Learn MoreHack The Box: WhiteRabbit Machine Walkthough – Insane Difficulity

18 Oct, 2025

Hack The Box: DarkCorp Machine Walkthrough – Insane Difficulity

Insane Machine BloodHoundCE, bloodyAD, BurpSuite, Challenges, evil-winrm, HackTheBox, hashcat, impacket, NetExec, Penetration Testing, sharpdpapi, ssh, Windows

Finished the Insane-level DarkCorp box on Hack The Box. Initial foothold came from registering on a webmail portal and abusing a contact form to deliver a payload that resulted in a reverse shell. From there I enumerated the app and DB, identified SQL injection and extracted hashes (cracked one to thePlague61780), recovered DPAPI master key material and additional credentials (Pack_beneath_Solid9!), and used those artifacts to escalate to root and retrieve root.txt. Valuable practice in web vectors, SQLi exploitation, credential harvesting, DPAPI analysis, and Windows privilege escalation. Happy to share high-level notes or mitigations.

#HackTheBox #Infosec #RedTeam #Pentesting #WindowsSecurity #CredentialHunting #CTF …

Learn MoreHack The Box: DarkCorp Machine Walkthrough – Insane Difficulity

9 Aug, 2025

Hack The Box: University Machine Walkthrough – Insane Walkthrough

Insane Machine Bloodhound, BurpSuite, Challenges, CVE-2023-33733, evil-winrm, HackTheBox, LocalPotato, Penetration Testing, python3, ssh, SSH key, Windows

Compromised university.htb by exploiting ReportLab RCE (CVE-2023-33733) to gain initial access as wao. Forged a professor certificate to impersonate george, then uploaded a malicious lecture to compromise Martin.T.

Escalated privileges by exploiting a scheduled task with a malicious .url file, used LocalPotato (CVE-2023-21746) for elevation on WS-3, and abused SeBackupPrivilege to extract NTDS.dit, ultimately retrieving Domain Admin credentials.

🔍 A great hands-on challenge combining web exploitation, privilege escalation, and Active Directory abuse.

#CyberSecurity #RedTeam #CTF #PrivilegeEscalation #HTB #InfoSec #WindowsExploitation #PenetrationTesting #EthicalHacking #HackTheBox …

Learn MoreHack The Box: University Machine Walkthrough – Insane Walkthrough

14 Jun, 2025

Hack The Box: Inflitrator Machine Walkthrough – Insane Difficulity

Insane Machine bitlocker, Bloodhound, BloodHoundCE, bloodyAD, BurpSuite, Certipy, Challenges, evil-winrm, HackTheBox, hashcat, impacket, john the ripper, kerbrute, Output Messenger, Penetration Testing, RDP, sqlite3, Windows, Wireshark

Successfully completed a two-stage Active Directory exploitation scenario involving both user access and privilege escalation. The first stage focused on identifying accounts that did not require Kerberos pre-authentication (AS-REP Roasting), allowing extraction and cracking of a user password hash to gain remote access and retrieve the user flag. In the second stage, a misconfigured certificate template (ESC4 vulnerability) within Active Directory Certificate Services was exploited to request a certificate impersonating a privileged user. This enabled full administrative access and retrieval of the root flag.

#CyberSecurity #ActiveDirectory #RedTeam #Kerberos #PrivilegeEscalation #ASREP #ADCS #ESC4 #PenetrationTesting #Infosec #HackTheBox #WindowsSecurity #CTF
Successfully completed a two-stage Active Directory exploitation scenario involving both user access and privilege escalation. The first stage focused on identifying accounts that did not require Kerberos pre-authentication (AS-REP Roasting), allowing extraction and cracking of a user password hash to gain remote access and retrieve the user flag. In the second stage, a misconfigured certificate template (ESC4 vulnerability) within Active Directory Certificate Services was exploited to request a certificate impersonating a privileged user. This enabled full administrative access and retrieval of the root flag.

#CyberSecurity #ActiveDirectory #RedTeam #Kerberos #PrivilegeEscalation #ASREP #ADCS #ESC4 #PenetrationTesting #Infosec #HackTheBox #WindowsSecurity #CTF
…

Learn MoreHack The Box: Inflitrator Machine Walkthrough – Insane Difficulity

5 Apr, 2025

Hack The Box: Ghost Machine Walkthrough – Insane Difficulty

Insane Machine adfs abuse attack, ADFSDump, ADFSSpoof, Bloodhound, BloodHoundCE, BurpSuite, Challenges, command injection, docker, efspotatoo, evil-winrm, Gitea, HackTheBox, hashcat, JokerShell, kerberos, LFI, Linux, mimkatz, Penetration Testing, responder, rubeus.exe, SQL, ssh

The initial foothold was gained by exploiting command injection on intranet.ghost.htb:8008/api-dev/scan/, which provided a reverse shell inside a Docker container. From there, I enumerated the environment and discovered credentials that allowed SSH access as Florence Ramirez. By extracting and converting a Kerberos ticket, I authenticated as a legitimate user, escalating access within the system. With access to the Windows environment, I retrieved NTLM hashes for the adfs_gmsa account and leveraged evil-winrm for lateral movement. A reverse shell was established using JokerShell, and privileges were escalated by enabling xp_cmdshell through a debug interface. After uploading EfsPotato.cs and disabling antivirus, I used Mimikatz and Rubeus.exe to dump credentials, ultimately achieving SYSTEM access. This led to the extraction of domain admin credentials and the retrieval of the root flag. Another Insane box down! 💀💻

#HackTheBox #RedTeam #CyberSecurity #PenTesting #PrivilegeEscalation #EthicalHacking …

Learn MoreHack The Box: Ghost Machine Walkthrough – Insane Difficulty

8 Feb, 2025

HackTheBox:MagicGardens Machine Walkthrough-Insane Difficulty

Insane Machine BurpSuite, Challenges, Django, docker, gobuster, HackTheBox, harvest, hashcat, insmod, Linux, Penetration Testing, python3, QRcode, ssh, XSS

Threatninja.net

Threatninja.net

Category Archives: Insane Machine