SEC586: Security Automation with PowerShell™

Overview

Even for seasoned PowerShell users, a deep and robust understanding of the language fundamentals can be incredibly powerful for writing more efficient, readable, and usable code. Section 1 of the course focuses on building a solid foundation upon which more complex use cases can then be constructed. With a focus on Blue Team specific functions, we'll frame the discussion around the PowerShell basics in terms that will be immediately useful for students. For example, common data structures are discussed as a fundamental aspect of PowerShell and immediately applied as Blue Team triage and analysis tactics. This base is built from the ground up and accessible to students with no prior scripting experience, but with enough nuance to shed light on the "why does it work this way" question for more seasoned PowerShell users. For professionals already familiar with the basic concepts, PowerPlay offers an interactive, out-of-band challenge system for students to drill various concepts and techniques related to the course material.

Exercises

• Hands-on PowerShell: Get comfortable with PowerShell cmdlets, objects, and the pipeline to start making meaningful tools
• Triage the VM: Quickly understand the state of a system, from networking details to process execution and removable devices
• Scripting in PowerShell: Leverage an understanding of the language basics to build high-quality tooling that will be supportable by Blue Teams
• Debugging: Save time and frustration, easily identifying complex bugs in PowerShell through built-in debugging capabilities and Pester tests
• Source Control: Become familiar with Git concepts to effectively manage version control

Topics

Getting to Know PowerShell

• Background and history
• Why PowerShell is such a good fit for Blue Teams
• How to use commands and find them
• Objects and pipelines as PowerShell differentiators
• Extending PowerShell with .NET

Blue Team Use Cases

• Network inspection
• Triage at the operating system level
• File discovery and inspection

Language Basics

• Variables, data structures, and flow control
• Input and output
• Functions and script blocks

PowerShell Environment

• Customizing the console
• Common development environments

Debugging

• Static code analysis
• Tracing and breakpoints
• Helpful tools like Pester and PSScriptAnalyzer

Source Control

• Git terminology
• Creating repositories and branches
• Managing code with pull requests
• Driving release pipelines from source control

Overview

PowerShell-based automation provides a unique, cross-platform mechanism for improving Blue Teams' speed of execution. This course section begins with a discussion on best practices to ensure code is highly functional, readable, and supportable. Students will leave with a deep understanding of how PowerShell works under the hood, but also with a sense of how to build tools that can be supported by team members less familiar with PowerShell.

This section transitions into taking the fundamentals and executing them at scale. PowerShell's remoting capabilities are flexible and nuanced, allowing for fine-tuning of code that needs to be executed against a fleet of systems. This section discusses PowerShell remoting capabilities and how to best use them to accomplish Blue Team use cases, from analysis and triage to response.

Next, a performance section addresses important aspects of PowerShell. Given its object-oriented nature, PowerShell is sometimes criticized for poor performance. However, if you understand the fundamentals, it becomes clear that very simple tweaks can optimize performance and reduce the overhead associated with these critiques. This section discusses optimizing code so that it is efficient both locally and once scaled out to a fleet of systems.

The section continues into building integration with other systems. With modern API-driven orchestration, PowerShell can glue together multiple systems for better troubleshooting, investigation, detection, and response. This understanding can unlock functionality that would not otherwise be possible between disparate systems.

Finally, protection, analysis, triage, and response techniques driven by PowerShell are enabled by Interactive Notebooks where analysts can combine documentation and executable code. Jupyter Notebooks and VS Code's .NET Interactive Notebooks are leveraged to help build PowerShell-based tooling that can be understood and executed by even novice analysts unfamiliar with PowerShell.

Exercises

• PowerShell Remoting: Understand how to run remote commands in a way that scales, and build a model for secure remote access
• Writing Usable PowerShell: Measure the impact of poorly versus well-written PowerShell, and leverage jobs and runspaces and compare performance
• Integrating Technologies: Build an API-based integration
• Interactive Notebooks: Build a triage notebook using VS Code and Jupyter

Topics

Best Practices

• Maximizing readability and reusability of code
• Designing tools with modularity in mind
• Handling unexpected conditions when working at scale

Remote Management

• PowerShell remoting basics and the underlying protocols
• Running remote commands
• Managing remote sessions
• Remoting endpoints/constrained endpoints
• Enabling WinRM-based and cross-platform remoting
• Designing around the double-hop problem

PowerShell Performance

• Coding techniques to maximize PowerShell performance
• Remoting performance tweaks
• Concurrency using native features

Integrations

• Making HTTP requests

• Web scraping

• API calls

• Authentication
• Handling session tokens
• Non-HTTP based integrations

Interactive Notebooks

• Jupyter Notebooks use cases
• PowerShell on Jupyter/.NET Interactive
• Use cases and implementation

Overview

Now that we have a strong understanding of the fundamentals, this course section focuses on ways to weaponize PowerShell both from an offensive and defensive perspective. The section begins with a focus on offensive PowerShell use cases. Threat actors have long used PowerShell as an attack platform, delivering fileless malware and living off the land using built-in capabilities. The next section turns this discussion around and focuses on the Blue Team aspects of controlling PowerShell execution.

The section then dives deep into log analysis and data parsing and discovery. The goal is to maximize the utility of native features of operating systems and applications while fully understanding how to find important data. If Blue Teams can identify sensitive data in unexpected locations, those data can be handled or protected properly.

The section concludes with a discussion of PowerShell as a platform to enable Blue Teams to work within DevOps development practices. As modern development teams transition practices, Blue Teams must adapt. Automation plays an important role in this process, as Blue Teams fight to scale capabilities to match modern development frameworks. PowerShell provides this automation platform and can be the catalyst to enable continuous assurance of critical business services.

Exercises

• Offensive PowerShell: Build a fileless keylogger that automatically exfiltrates keystrokes to cloud storage
• Controlling PowerShell: Analyze the impact of a stronger security posture surrounding PowerShell usage in the enterprise
• Efficient Log Analysis: Understand how to efficiently analyze and filter Windows events and plaintext log files, and find attacks within sample log files
• Parsing and Discovery: Build tools to extract important data from unstructured text-based logs and use these same techniques for sensitive data discovery
• DevOps: Leverage PowerShell as an orchestration engine, building containers for automated web application scanning and identifying potentially compromised containers in the environment

Topics

Offensive PowerShell

• Common tactics used by attackers leveraging PowerShell
• Fileless implementation techniques
• .NET utilization by PowerShell-based attack tools

Controlling PowerShell

• Limiting attack surface on PowerShell-enabled systems
• Controlling, not attempting to block, PowerShell in the enterprise
• Just Enough Administration for enabling secure usage of administrative PowerShell sessions

Log Analysis

• Enabling appropriate logging
• Reading and filtering Windows Event Logs
• Reading and filtering plaintext logs

Text Parsing

• Regular expressions and string operations to enable efficient parsing

DevOps

• Automating static and dynamic application security testing
• Pipeline assurance automation
• Container interaction, security assessment, and triage

Overview

This course section focuses on better understanding one's own environment, maximizing visibility and testing defensive capabilities using PowerShell. The section begins with in-depth discussions on hardening infrastructure and maximizing visibility and detection capabilities. For basics such as ensuring that proper access controls exist, the theory is simple. But using traditional techniques, scaling in practice is difficult. With an automation platform like PowerShell, hardening and auditing practices can be scaled with ease, providing consistent assurance.

Next, Desired State Configuration, PowerShell's configuration-as-code utility, can be used to consistently define and configure infrastructure using PowerShell to help ensure system integrity. Additional hardening techniques are discussed based on maximizing native security functionality.

The section then turns to improving understanding of visibility and detection capabilities in a repeatable format via automated testing techniques that provide for a reliable and repeatable means of measuring capabilities. The focus here is to use PowerShell as a testing utility to identify visibility and detection gaps both in preventive and detective controls, but also in operational processes.

Finally, a common challenge faced by Blue Teams is the overwhelming amount of data generated by endpoints and security tooling. While large volume is meant to facilitate proper detection, it can be interpreted as noise and actually harm an organization's ability to detect threats. We'll discuss analysis techniques that use PowerShell to filter through some of this noise and provide the ability to make better decisions based on available data.

Exercises

• Advanced Detections: Leverage native functionality to maximize hardening efforts with a focus on enabling efficient detection
• Desired State Configuration: Leverage DSC to harden a system and turn it into an incident response powerhouse
• Measuring Visibility with Atomic Red Team: Leverage Atomic Red Team to test and maximize visibility
• Analyzing Large Data Sets: Quickly make sense of large volumes of data using statistical analysis, and leverage custom PowerShell to create unique PowerShell objects meant to solve specific problems

Topics

System Hardening

• Filesystem and registry controls
• Management of native endpoint functionality

Desired State Configuration

• Benefits of Configuration as Code
• DSC architecture and deployment options
• DSC syntax
• Finding, building, and implementing DSC resources
• Workflow and use cases

Know Thyself

• Understanding operational capabilities
• Visibility analysis
• Testing compliance with and the visibility of the CIS Critical Security Controls against MITRE ATT&CK

Analyzing Large Data Sets

• Feeding data to SIEMs and Big Data systems
• Analysis techniques to identify events of interest
• N-Gram analysis for identifying unusual strings
• PowerShell class structure and implementation

Overview

With hardening and protection mechanisms now having been covered, this course section focuses entirely on detection and response strategies enabled by PowerShell automation.

Advanced detection techniques such as Event Tracing for Windows and deception on endpoints and the network are implemented to provide deep visibility and weaponize existing infrastructure against threat actors. These techniques can be automated at scale to turn a "normal" enterprise network into a mine field, providing deep visibility to Blue Teams while forcing an attacker to work even more slowly and methodically to evade detection.

Baselining is layered on top of these techniques to provide an ability to understand normal operating circumstances and identify outliers from that dataset. Baseline deviation detection and file integrity monitoring techniques are implemented in a way that is supportable at scale and, of course, automated using PowerShell.

The course section concludes by covering response techniques meant to maximize visibility and help an operations team better understand if anomalous conditions warrant further containment and investigation. Once malicious intent is identified, response techniques focused on containment can be automated to mitigate additional harm. Layering these response techniques inside of automation playbooks can ensure proper response, containing threats but also enabling teams to quickly identify false positives and avoid unnecessary end-user friction and business impact.

Exercises

• Event Tracing for Windows: Become familiar with ETW providers and their use for detection purposes
• Baseline Analysis: Build a baseline object that protects integrity while profiling network and user behavior
• Deception: Implement several deception techniques to identify attacker behavior
• Response - Visibility: Build automation to more quickly understand context around an event
• Response - Containment: Build automation to more quickly contain threats

Topics

Event Tracing for Windows

• Architecture and Blue Team use cases
• Providers
• Trace sessions
• Packet captures in PowerShell
• ETW tampering and detection

Baselining

• Converting baseline data to objects and storing them securely
• Strategies to create baselines
• Types of baselines and implementations
• PowerShell-based tools for baselining

Automating Deception

• Network deception techniques
• System deception techniques
• User deception techniques
• Cloud deception techniques

Short-term Response - Visibility

• Network and user-based enumeration
• Enabling deeper auditing as an ad hoc response
• Enrichment of existing data

Short-term Response - Containment

• Mitigating credential theft impact
• System containment - process and behavior restriction
• Network containment

Overview

The final section of SEC586 focuses entirely on hands-on application of the skills built throughout the week. Working in teams, each group must solve challenges ranging from log analysis to containment tactics. Several different challenges with increasing levels of difficulty will require groups to work together, mastering PowerShell from the perspective of Blue Team workloads, and providing a safe environment to work with PowerShell while under pressure. Challenges will ensure a deep understanding of the concepts covered throughout SEC586 while offering a fun and competitive platform to test and further build these skills.