Core Security Outflank Security Tooling vs Pupy: Side-by-Side Comparison (2026)

Core Security Outflank Security Tooling: Red team toolkit for EDR evasion, initial access, and post-exploitation. built by Core Security. Core capabilities include Advanced payload generation with AV/EDR evasion and anti-forensic capabilities, Office Intrusion Pack for phishing via malicious MS Office macros, Steganography-based payload concealment within image files..

Pupy: Pupy is an open-source, cross-platform C2 framework that provides remote access and control capabilities for compromised systems across Windows, Linux, OSX, and Android platforms..

Both serve the Offensive Security market but differ in approach, feature depth, and target audience.

Core Security Outflank Security Tooling is developed by Core Security. Pupy is open-source with 8,948 GitHub stars. Vendor maturity, funding stage, and team size can be important factors when evaluating long-term viability and support quality.

Core Security Outflank Security Tooling and Pupy serve similar Offensive Security use cases: both are Offensive Security tools, both cover Post Exploitation, C2, Red Team. Key differences: Core Security Outflank Security Tooling is Commercial while Pupy is Free, Pupy is open-source. Review the feature comparison above to determine which fits your requirements.