Tag kerberos

Hack The Box: Checkpoint Machine Walkthrough Medium Difficulty

Just finished the Checkpoint machine on Hack The Box (Medium difficulty) and it was a really enjoyable Active Directory box with some modern and creative attack paths.

I started with the provided credentials for `alex.turner`. After some enumeration I discovered that a previously deleted account (`mark.davies`) could be restored and that this account had write access to a share called DevDrop. This share was used by the organisation to stage VS Code extensions.

By creating a malicious VSIX extension targeting VS Code engine version 1.118.0 and dropping it on the share, a scheduled task automatically installed the extension and gave me a reverse shell as `ryan.brooks`. This was a really clean example of abusing enterprise software deployment processes.

From the `ryan.brooks` foothold I used Rubeus to obtain a TGT, then leveraged bloodyAD to create a malicious dMSA under a writable OU and impersonated a higher-privileged account. This eventually granted access to a VMBackups share containing a Windows Server memory dump. Using Volatility I extracted the local Administrator NTLM hash from the dump, authenticated with Evil-WinRM, and captured the root flag.

Overall, Checkpoint does a great job of chaining together several current techniques: writable shares for extension abuse, deleted object restoration, dMSA abuse, and memory forensics. It’s a solid Medium box that feels realistic and rewards careful enumeration.

Would recommend it to anyone working on modern Windows / Active Directory attack paths.

#HackTheBox #CyberSecurity #PenetrationTesting #ActiveDirectory #RedTeam #HTB #InfoSec #WindowsSecurity #PrivilegeEscalation #Kerberos #MemoryForensics

Hack The Box: Pirate Machine Walkthrough – Hard Difficulity

Completed the Hack The Box “Pirate” machine, a hard-difficulty Active Directory challenge that required chaining multiple attack paths rather than relying on a single vulnerability.

The enumeration phase uncovered domain users, pre-created computer accounts, GMSAs, delegation relationships, and an exposed internal network. Access to gMSA_ADFS_prod$ led to DC01 and enabled an internal pivot to WEB01. From there, the attack chain involved GMSA credential retrieval, NTLM relay, authentication coercion, shadow credentials, certificate-based authentication, and Kerberos ticket abuse.

The privilege escalation path continued through constrained delegation and resource-based constrained delegation. Kerberos ticket manipulation ultimately provided Administrator access to the domain controller, followed by a SYSTEM-level shell and extraction of domain credentials from NTDS.dit. Both the user and root flags were successfully obtained.

Another challenging AD machine completed and another deep dive into Windows authentication, delegation, and privilege escalation.

#HackTheBox #HTB #CyberSecurity #PenetrationTesting #ActiveDirectory #RedTeam #Kerberos #NTLMRelay #ShadowCredentials #GMSA #PrivilegeEscalation #WindowsSecurity #Cybersecurity #Infosec #HTBWriteup

Hack The Box: Logging Machine Walkthrough – Medium Difficulty

Completed another Hack The Box machine focused on Active Directory exploitation and privilege escalation.

The attack involved SMB enumeration, credential discovery through log analysis, Kerberos authentication, Shadow Credentials abuse, and DLL hijacking to gain user-level access. Further enumeration revealed a WSUS infrastructure weakness, allowing exploitation through Kerberos delegation abuse, certificate-based authentication, and a WSUS machine-in-the-middle attack to achieve Domain Admin privileges. This challenge strengthened my understanding of modern AD attack paths, Kerberos abuse techniques, and enterprise infrastructure security.

#HackTheBox #HTB #CyberSecurity #ActiveDirectory #RedTeam #PenetrationTesting #OffensiveSecurity #EthicalHacking #InfoSec

Hack The Box: Signed Machine Walkthrough – Medium Difficulity

After escalating to a SYSTEM-level PowerShell reverse shell using xp_cmdshell and a base64-encoded payload that called back to my netcat listener on port 9007, I navigated to the user profile and read the user flag directly with type user.txt.

With full sysadmin rights on the SQL instance as SIGNED\Administrator (thanks to a forged silver ticket with Domain Admins membership), I enabled xp_cmdshell, launched a reverse shell to land SYSTEM access, then grabbed the root flag from

Box fully pwned — domain admin and SYSTEM in the bag!

#HackTheBox #HTBSigned #PenetrationTesting #CyberSecurity #PrivilegeEscalation #ActiveDirectory #RedTeam #CTF #EthicalHacking #OffensiveSecurity

Hack The Box: RustyKey Machine Walkthrough – Hard Difficulity

Authenticated to rustykey.htb as bb.morgan after exploiting Kerberos flows and resolving a time sync issue: obtained a TGT (bb.morgan.ccache), set KRB5CCNAME, and used evil‑winrm to capture the user flag.
Escalated to SYSTEM by abusing machine account and delegation: IT‑COMPUTER3$ was used to modify AD protections and reset ee.reed’s password, S4U2Self/S4U2Proxy impersonation produced backupadmin.ccache, and Impacket was used to deploy a service payload to achieve a SYSTEM shell and capture the root flag.

#CyberSecurity #RedTeam #Kerberos #ActiveDirectory #PrivilegeEscalation #HackTheBox #Impacket #WindowsAD

Hack The Box: Certificate Machine Walkthrough – Hard Difficulty

I recently completed the "Certificate" challenge on Hack The Box: after extracting and cracking a captured authentication hash I gained access to a user account (lion.sk) and retrieved the user flag, then progressed to full system compromise by responsibly exploiting weak certificate‑based authentication controls—obtaining and converting certificate material into elevated credentials to capture the root flag. The exercise reinforced how misconfigurations in certificate services and poor time synchronization can create powerful escalation paths, and highlighted the importance of least‑privilege, strict enrollment policies, and monitoring certificate issuance. Great hands‑on reminder that defensive hygiene around PKI and identity services matters.

#CyberSecurity #HTB #Infosec #ADCS #Certificates #PrivilegeEscalation #RedTeam #Pentesting

Hack The Box: Vintage Machine Walkthrough – Hard Difficulty

Recently completed an Active Directory penetration test where I obtained both the user and root flags through a series of Kerberos and privilege escalation attacks. I first exploited a weak password on a legacy computer account (fs01$) to retrieve a Kerberos TGT and extract the gMSA password. After reactivating a disabled service account (svc_sql), making it ASREPRoastable, and cracking its hash, I gained credentials for another domain user and authenticated via Evil-WinRM to capture the user flag. For the root flag, I decrypted DPAPI-protected secrets to access a higher-privileged account (c.neri_adm), added a compromised service account to a privileged group, assigned an SPN, and performed a Kerberos delegation attack to impersonate a domain admin, ultimately achieving SYSTEM-level access and capturing the root flag. Great experience applying Kerberos exploitation techniques and privilege escalation strategies in a real-world scenario!

hashtag#ActiveDirectory hashtag#PenetrationTesting hashtag#Kerberos hashtag#OffensiveSecurity hashtag#RedTeam hashtag#CyberSecurity hashtag#ASREPRoasting hashtag#DPAPI hashtag#PrivilegeEscalation hashtag#HackTheBox hashtag#Infosec hashtag#HacktheBox

Hack The Box: Ghost Machine Walkthrough – Insane Difficulty

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