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The Mindset

Pillaging is post-exploitation with the goal of extracting value. On Windows you’re hunting:
  • Credentials — saved passwords, hashes, tokens, keys, config secrets
  • Sensitive data — customer records, financial files, PII (the stuff that proves impact in a report)
  • Infrastructure intel — domain info, internal hostnames, connection strings for lateral movement
  • Persistence material — anything that helps you keep or regain access
The difference between enumeration and pillaging is intent. Enumeration maps the system; pillaging strips it.

Start With Automated Enumeration

Before manual hunting, run an automated enumeration script. These find privilege-escalation paths and sensitive files far faster than you can by hand.

winPEAS

The Windows equivalent of linPEAS — checks for service misconfigs, weak permissions, stored credentials, autostart entries, and dozens of other privesc vectors in one run.

Other Tools

Run winPEAS first to get the lay of the land, then manually verify anything it flags before exploiting. Automated tools produce false positives, and on a defended box they’re noisy — know that running them may generate alerts.

Hunting Sensitive Files

This is the core of pillaging — finding the files that contain credentials or prove impact.

Search by Filename and Extension

Search File Contents for Credentials


Where Credentials Hide on Windows

A targeted tour of the highest-value locations:
The highest-value credential locations:
cmdkey /list shows stored credentials you may not know the password for — but you can often still use them with runas /savecred, executing commands as that account without ever seeing the password.

The Exfiltration Endgame

Finding the data is half the job — extracting it and proving impact is the other half. Picture the classic scenario: you’ve landed on a box, escalated, and found customer_database.csv sitting in a shared folder — thousands of customer records with names, emails, and payment details.

Confirm What You’ve Found

Exfiltrate It

Why This Matters — Impact & Reporting

This is where pentesting connects to the real world. That CSV isn’t just a flag — it represents:
  • PII exposure — names, addresses, payment data. Under GDPR, a breach of this data can mean fines up to 4% of global annual revenue
  • Demonstrated business impact — “we got admin” is abstract; “we exfiltrated 40,000 customer records including payment details” is a board-level conversation
  • The evidence that justifies the engagement — proving real data was reachable is what drives organizations to fix things
In a real engagement, do not actually exfiltrate sensitive PII unless your rules of engagement explicitly permit it. Usually you prove access — a screenshot of the first few rows, the record count, the file path and permissions — without removing the data. Removing real customer data can itself create legal liability. Know your ROE.

Pillaging Checklist


Next: Windows Security Mechanisms — UAC, AppLocker, Defender, and the defenses you’ll work around.