Protected File Transfers

πŸ” Protected File Transfers – Doing It the Right Way

As penetration testers, we often deal with sensitive data:

  • πŸ§‘β€πŸ€β€πŸ§‘ User credentials

  • πŸ—ƒοΈ Domain enumeration data

  • πŸ› οΈ Tools like NTDS.dit, LSASS, and scan logs

It’s critical that we encrypt anything we extract β€” both to protect clients and our own reputation. A simple oversight (like exfiltrating in plaintext) can lead to serious consequences. 🚨


🧠 Pro Tip

If your goal is DLP testing, use dummy data that mimics sensitive content. Never transfer real PII, credentials, or trade secrets unless authorized.


πŸͺŸ File Encryption on Windows

A lightweight and powerful PowerShell script that encrypts/decrypts:

  • πŸ” Strings

  • πŸ“„ Files


πŸ“₯ Importing the Script

After that, you can use it like any other cmdlet. βœ…


πŸ“¦ Usage Examples

1️⃣ Encrypt a String (Base64 output)

2️⃣ Decrypt a String

3️⃣ Encrypt a File

πŸ”„ Output: scan-results.txt.aes

4️⃣ Decrypt a File


🐧 File Encryption on Linux

πŸ”’ OpenSSL Encryption

OpenSSL is built into most Linux distros and allows you to encrypt files with AES-256 πŸ’ͺ

πŸ” Encrypt a File

You’ll be prompted to enter a password πŸ”‘


πŸ”“ Decrypt a File

Same password required to decrypt.


πŸ›‘οΈ Security Best Practices

  • βœ… Use strong, unique passwords for each engagement

  • ❌ Avoid using the same encryption key across clients

  • ⚠️ If encryption is not an option, do not exfil highly sensitive files

  • πŸ’¬ Communicate encryption methods clearly in your report


🧳 Transfer Tips

Once encrypted, you can safely transfer files using:

  • βœ… HTTPS

  • βœ… SFTP

  • βœ… SCP/SSH

  • βœ… Encrypted tunnels

❌ Avoid: Plain HTTP, SMB, FTP unless you're testing insecure protocols


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