Target: Windows

Proving Grounds: Squid

This lab demonstrates using a Squid proxy to enumerate open ports on a target and gain initial access via phpMyAdmin with default credentials. Learners will escalate privileges by recovering restricted LOCAL SERVICE privileges through scheduled tasks. Finally, they will exploit the SeImpersonatePrivilege using PrintSpoofer to achieve a SYSTEM shell. This lab emphasizes proxy exploitation, privilege recovery, and abuse of impersonation rights.

Proving GroundsAuthorized lab writeupCybersecurity portfolio

Authorized-lab note: This writeup documents activity performed exclusively in an authorized Offensive Security Proving Grounds lab. It is shared for educational and portfolio purposes.

In this lab, we will enumerate ports behind a Squid proxy to gain an initial foothold through phpMyAdmin. Privileges will then be elevated by creating scheduled tasks to enable restricted privileges. This lab focuses on exploiting proxy configurations and privilege escalation methods.

Scenario

This lab demonstrates using a Squid proxy to enumerate open ports on a target and gain initial access via phpMyAdmin with default credentials. Learners will escalate privileges by recovering restricted LOCAL SERVICE privileges through scheduled tasks. Finally, they will exploit the SeImpersonatePrivilege using PrintSpoofer to achieve a SYSTEM shell. This lab emphasizes proxy exploitation, privilege recovery, and abuse of impersonation rights.

Learning objectives

After completion of this lab, learners will be able to:

Enumeration

This block performs reconnaissance or local enumeration. Its output is reviewed for services, files, accounts, and other leads that guide the next step.

# The scan output identifies the target's exposed services and their versions.

PORT      STATE SERVICE       VERSION
135/tcp   open  msrpc         Microsoft Windows RPC
139/tcp   open  netbios-ssn   Microsoft Windows netbios-ssn
445/tcp   open  microsoft-ds?
3128/tcp  open  http-proxy    Squid http proxy 4.14
|_http-server-header: squid/4.14
|_http-title: ERROR: The requested URL could not be retrieved
49666/tcp open  msrpc         Microsoft Windows RPC
49667/tcp open  msrpc         Microsoft Windows RPC
Service Info: OS: Windows; CPE: cpe:/o:microsoft:windows

Host script results:
| smb2-security-mode: 
|   3.1.1: 
|_    Message signing enabled but not required
| smb2-time: 
|   date: 2026-06-17T23:06:39
|_  start_date: N/A

Takeaways

This lab reinforced the value of methodical enumeration, evidence-driven hypothesis testing, and validating each access-control boundary in an authorized environment.