As macOS endpoint controls continue to evolve, adversaries are consistently adapting their TTPs to defeat Apple’s ever-changing security frameworks. Although .dmg files remain a popular initial access vector, the traditional “right-click and open” method has become largely ineffective—especially with the security enhancements introduced in macOS Sequoia.

This analysis delves into some contemporary disk-image malware campaigns, their execution primitives and obfuscation techniques.

The Demise of “Right-Click Open”

The “right-click open” method of bypassing Gatekeeper, while helpful for a long time, has become less useful to attackers. With the advent of macOS Sequoia, Apple significantly tightened the Gatekeeper and notarization requirements. This has made it harder for unsigned or malicious applications to directly execute, even with a user’s explicit attempt to override built-in controls. While this is a positive step for overall security, it has pushed attackers to find new avenues for initial compromise.

In the evolving landscape of macOS security, NorthPoleSec’s Santa has earned a solid reputation as a flexible and lightweight endpoint security tool. Originally developed by Google, Santa acts as a binary whitelisting/blacklisting system, but in recent iterations, it also provides incredibly powerful features including file-access authorization. This lesser-known feature is a game-changer for protecting sensitive data on disk, such as session tokens, SSH keys, and browser cookies.

In this post, we’ll take a look at how Santa’s file access authorization mechanism works and how you can configure it to prevent common threat actor behaviors on macOS endpoints.