Sophisticated PyPI Attack Campaign Leverages Gmail SMTP Servers to Evade Detection

CyberSecureFox 🦊

Security researchers at Socket have uncovered a sophisticated attack campaign targeting the Python Package Index (PyPI), revealing seven malicious packages that employed an innovative attack vector through Gmail SMTP servers and WebSocket connections. This discovery highlights a concerning evolution in supply chain attacks, demonstrating how threat actors are leveraging trusted services to bypass security controls.

Long-Term Presence and Widespread Impact

The investigation revealed that these malicious packages maintained an alarming presence in the PyPI repository for up to four years, with one package accumulating over 18,000 downloads. The threat actors cleverly disguised their malicious code by impersonating Coffin, a legitimate tool used for integrating Jinja2 templates with Django projects, significantly expanding their potential attack surface.

Advanced Two-Stage Attack Methodology

The malware employed a sophisticated two-stage attack strategy that demonstrated remarkable technical sophistication. Initially, the malicious code established connections to Gmail’s SMTP server (smtp.gmail.com) using pre-configured credentials. This approach proved particularly effective as Gmail’s trusted status allowed the malware to operate under the radar of many security monitoring systems.

Persistent Command and Control Infrastructure

Following initial access, the malware established an encrypted WebSocket connection over SSL to the attackers’ command and control server. This secure bi-directional tunnel enabled comprehensive system compromise, allowing attackers to execute remote commands and exfiltrate sensitive data while maintaining persistent access to infected systems.

Cryptocurrency-Focused Attack Campaign

Technical analysis of the attack infrastructure, including email addresses like [email protected], strongly indicates that the campaign primarily targeted cryptocurrency assets. The tactics, techniques, and procedures (TTPs) exhibited notable similarities to previous attacks targeting Solana private keys, suggesting a possible connection to known cryptocurrency theft operations.

This incident serves as a critical reminder of the evolving threats within the software supply chain. Organizations must implement comprehensive security measures, including automated package scanning, dependency verification, and continuous monitoring of third-party components. Security teams should pay particular attention to network connections to trusted services that could be exploited as command and control channels. The implementation of strict package verification procedures, along with regular security audits of development dependencies, has become essential for maintaining robust application security in modern development environments.

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