This write-up discusses advanced SSH tunneling techniques for network penetration testing and red team engagements. It focuses on using the native OpenSSH client in Windows 10/11 to create reverse dynamic SOCKS proxies, allowing testers to access internal networks and run offensive tools remotely. The guide covers: 1. Using the -R flag for reverse dynamic proxies 2. Techniques to bypass corporate firewalls, including using Azure domains and ASN IP ranges 3. Methods for payload delivery and data exfiltration using SCP 4. OpSec-safe PowerShell script execution through SSH The write-up also includes recommendations for defenders, such as removing the SSH client from non-technical staff endpoints, securing corporate firewall settings, and monitoring for SSH binary execution.
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