Automating Red Team Operations with Custom Tools

Automating Red Team Operations with Custom Tools

Introduction

Modern red teaming goes far beyond technical proficiency — it’s about operating with stealth, precision, and adaptability.
While commodity tools offer convenience, they often introduce detectable artifacts, limited flexibility, and noisy behavior.

This article explores how developing custom tools can fill critical operational gaps and elevate red team performance across the full adversary lifecycle.

Why Custom Tooling Makes a Difference

Off-the-shelf tools often fall short in mature environments where EDR, NDR, and behavioral analytics are in place.
Purpose-built tooling provides:

• Payloads tailored to specific defenses and trust models
• Modular automation for high-volume or repetitive tasks
• OPSEC-friendly behavior via obfuscation and traffic shaping
• Adaptive logic for shifting network, identity, and access conditions

When the objective is stealth and success, tooling should be part of the threat model — not the limitation.

Where Automation Pays Off

Custom automation has proven valuable in:

• Reconnaissance chaining: Combining OSINT, DNS, and certificate data to map weak links
• Credential attacks: Smart spraying with time-windowed logic and user profiling
• Initial access & staging: Using beacon-aware delivery techniques that blend into legitimate traffic
• Lateral movement: Auto-enumeration and path simulation based on real-time domain feedback
• EDR evasion: Payload shaping informed by environment-aware reconnaissance

Designing Effective Red Team Tooling

Successful toolchains are built around core design principles:

• Lightweight and fileless execution to minimize footprint
• Covert C2 channels, including HTTP/3, DNS-over-HTTPS, or internal-only protocols
• Modular plugin systems that allow flexible reuse and adaptation
• Failsafes: Built-in kill-switches, time-based expiry, and logic to disable in sandboxed conditions

These principles make tooling more robust, reusable, and secure across engagements.

Case Snapshot: Bespoke Phishing Infrastructure

In a recent red team engagement, we developed a custom phishing platform that:

• Rotated infrastructure domains dynamically
• Adapted payload behavior based on SPF/DKIM results
• Embedded malicious components in Slack and Microsoft Teams interactions

Results:

• 78% success rate bypassing email security filters
• 46% click-through on targeted lures
• Complete C2 establishment in under 5 minutes for several target accounts

These results far exceeded what commodity phishing kits typically deliver.

Lessons Learned

Custom automation doesn’t eliminate the need for skilled operators — it amplifies their impact.
Rather than adapting tactics to fit the limitations of tools, teams should build tools that serve the mission.
This alignment of goals and capabilities leads to faster operations, reduced exposure, and better outcomes.

Recommendations

• Invest in in-house red team tooling — especially for stealth, evasion, and infrastructure
• Limit dependence on open-source tools in high-assurance environments
• Build composable automation workflows that support reusability across different threat models
• Involve red teamers in the development process to ensure operational relevance and realism

Want to Build or Enhance Your Red Team Toolchain?

Out-of-the-box tools only go so far — especially when simulating nation-state TTPs or probing high-trust environments.
If you're serious about offensive capability, you need more than public scripts and one-size-fits-all frameworks.

At Siber Ninja, we help red and purple teams build sharper, stealthier, and more adaptable tooling:

• Custom infrastructure for red team simulations and C2 environments

• Bespoke exploit automation and payload generation

• Operator-grade tooling hardened for real-world operations

• Expert-led training to operationalize and scale your custom stack

• Contact us to discuss your red team needs

• Explore our Offensive Security Consulting for custom tooling and simulation design

• Train your team with real-world offensive tradecraft

Tired of modifying public tools that weren’t built for your op?
Let’s build what your adversaries would — before they do.