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21 February 2025

Password Spraying Top 10

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Top 10 Password Spraying Tools for Red Team Operations

Password spraying is a widely used technique in cybersecurity, particularly in Red Team operations, where adversaries attempt to gain unauthorized access by testing a single password across multiple user accounts. This method is designed to bypass account lockout mechanisms that are triggered by multiple failed login attempts on a single account. With the increasing adoption of cloud services like Microsoft 365 (formerly Office 365) and Azure Active Directory (Azure AD), password spraying has become a critical focus for both attackers and defenders.

In this report, we explore the top 10 most starred tools on GitHub that are specifically designed for password spraying against online services, including Microsoft authentication endpoints. These tools are invaluable for Red Teamers, penetration testers, and security researchers aiming to assess the resilience of authentication systems. Each tool offers unique features, ranging from user enumeration to advanced evasion techniques, making them highly effective in simulating real-world attack scenarios.

The tools listed here are open-source and widely recognized in the cybersecurity community. They are intended for ethical use in controlled environments to identify and mitigate vulnerabilities. Below are the highlights of the most popular password spraying tools:

  1. SprayingToolkit
    A Python-based toolkit designed to streamline password spraying attacks against Microsoft services like Lync, Skype for Business, Outlook Web Access (OWA), and Office 365. It simplifies the process and includes features like jitter and delay to avoid detection.

  2. MSOLSpray
    A PowerShell script for password spraying Microsoft Online accounts (Azure/O365). It logs detailed results, such as whether MFA is enabled, accounts are locked, or users do not exist, making it a comprehensive tool for Azure AD assessments.

  3. Spray365
    A Go-based tool that introduces a customizable two-step password spraying approach. It includes features to bypass Azure Smart Lockout and insecure conditional access policies, making it highly effective for Microsoft accounts.

  4. TREVORspray
    A modular password sprayer written in Python, featuring threading, SSH proxying, and loot modules. It is one of the most feature-rich tools available for password spraying.

  5. SharpSpray
    A Windows domain password spraying tool written in C#. It integrates seamlessly with Cobalt Strike and is optimized for Red Team operations in Active Directory environments.

  6. MSOLSpray.py
    A Python port of the original MSOLSpray PowerShell tool. It retains the same functionality while offering cross-platform compatibility for password spraying Microsoft Online accounts.

  7. CredMaster
    A refactored and enhanced version of the CredKing tool, leveraging FireProx APIs for IP rotation. This ensures anonymity and bypasses throttling during password spraying attacks.

  8. Omnispray
    A Python-based modular framework designed to replace older tools like o365spray. It supports enumeration and spraying across multiple targets and applications, offering extensive flexibility.

  9. TeamFiltration
    A cross-platform framework for enumerating, spraying, exfiltrating, and backdooring Office 365 and Azure AD accounts. It is a versatile tool with numerous features for Red Teamers.

  10. Go365
    A Go-based tool that performs user enumeration and password spraying against Office 365 accounts. It utilizes a unique SOAP API endpoint, making it distinct from other tools.

These tools are instrumental in identifying weaknesses in authentication systems and improving organizational security. However, they must be used responsibly and within the boundaries of ethical hacking practices. For more information on each tool, visit their respective GitHub repositories.

Table of Contents

Introduction to Password Spraying and Its Relevance to Red Teaming

Understanding Password Spraying Attacks

Password spraying is a brute-force attack technique where an attacker attempts to authenticate multiple accounts using a single password or a small set of passwords. This approach is designed to bypass account lockout mechanisms, which are typically triggered after multiple failed login attempts for a single account. By spreading the attempts across numerous accounts, attackers minimize the risk of detection and account lockouts.

In the context of red teaming, password spraying is a crucial tactic for simulating real-world attacks against organizations. It allows red teamers to test the resilience of authentication systems, identify weak credentials, and assess the effectiveness of monitoring and detection mechanisms.

Password spraying is particularly effective against online services such as Microsoft Office 365 (O365) and Azure Active Directory (Azure AD), which are widely used by organizations. These services often have publicly accessible authentication endpoints, making them prime targets for attackers.

Key Features of Password Spraying Tools

Password spraying tools are designed to automate the process of testing credentials against authentication endpoints. Some of the key features of these tools include:

  1. Username Enumeration: Many tools include functionality to identify valid usernames before initiating the spraying attack. This reduces the number of invalid login attempts and increases the efficiency of the attack.

  2. Rate Limiting and Jitter: To avoid detection and account lockouts, password spraying tools often include options to introduce delays between login attempts or randomize the order of attempts.

  3. Modular Frameworks: Advanced tools provide modular frameworks that allow users to customize the attack parameters, such as the authentication protocol, target domain, and password list.

  4. Proxy Support: To evade IP-based rate limiting, some tools support the use of proxies or services like FireProx, which dynamically rotates IP addresses.

  5. Integration with Other Tools: Many password spraying tools are designed to work seamlessly with other red teaming tools, such as CrackMapExec and Impacket.

Top 10 Most Starred Password Spraying Tools on GitHub

The following is a curated list of the most popular password spraying tools on GitHub, based on their star count and relevance to red teaming:

1. SprayingToolkit

2. o365spray

3. DomainPasswordSpray

4. Go365

5. SprayCannon

6. CredMaster

7. MSOLSpray

8. SharpSpray

9. TeamFiltration

10. TREVORspray

Ethical Considerations and Best Practices

While password spraying is a valuable technique for red teaming, it is essential to use these tools responsibly and ethically. Organizations should ensure that all testing is conducted with proper authorization and within the scope of the engagement. Additionally, red teamers should follow these best practices:

  1. Minimize Impact: Use rate limiting and jitter to avoid triggering account lockouts or disrupting normal operations.

  2. Document Findings: Provide detailed reports on the vulnerabilities identified and recommendations for remediation.

  3. Collaborate with Blue Teams: Share insights and findings with the organization’s blue team to improve detection and response capabilities.

  4. Stay Updated: Regularly update tools and techniques to stay ahead of evolving threats and detection mechanisms.

By adhering to these best practices, red teamers can effectively simulate real-world attacks and help organizations strengthen their security posture.

Advanced Features in Password Spraying Tools for Microsoft Authentication Endpoints

Dynamic IP Rotation and Proxy Integration

Password spraying tools targeting Microsoft authentication endpoints often incorporate dynamic IP rotation and proxy integration to avoid detection and bypass rate-limiting mechanisms. These features are particularly useful when targeting services like Azure Active Directory and Office 365, where failed login attempts from the same IP address can trigger account lockouts or alert administrators.

These features go beyond the basic proxy support mentioned in previous reports by emphasizing advanced configurations like FireProx integration and round-robin proxying.

Modular Frameworks and Extensibility

Modern password spraying tools are designed with modular frameworks that allow users to customize and extend their functionality. This flexibility is crucial for red team operations targeting diverse authentication endpoints.

This section expands on the modular frameworks discussed in earlier reports by highlighting specific tools and their unique implementations, such as execution plans and template-based modules.

Real-Time Detection Evasion

Password spraying tools increasingly incorporate features to evade real-time detection mechanisms employed by Microsoft authentication endpoints.

These features build upon the rate-limiting and jitter functionalities mentioned in previous reports by focusing on advanced evasion techniques like user-agent spoofing and low-and-slow operations.

Enhanced Logging and Reporting

Detailed logging and reporting are essential for assessing the success of password spraying operations and identifying potential security gaps.

This section complements earlier discussions on logging by emphasizing advanced features like webhook notifications and SIEM integration.

Multi-Protocol Support

Password spraying tools are increasingly supporting multiple authentication protocols to target a broader range of services.

This section extends the discussion on multi-protocol support by highlighting tools with cross-platform capabilities and custom endpoint configurations.

Advanced Credential Management and Execution Plans

Password spraying tools have evolved to include sophisticated features for managing credentials and planning attacks. This section focuses on capabilities that enhance operational efficiency and reduce the risk of detection.

Credential Execution Plans

Tools like Spray365 introduce the concept of execution plans, which allow users to predefine the parameters of a password spraying operation. These plans include details such as target domains, username lists, password lists, and delay configurations. Execution plans provide several advantages:

Dynamic Credential Rotation

Several tools, including CredMaster and MSOLSpray, leverage dynamic credential rotation to evade detection. Features include:

Integration with Proxy and IP Rotation Mechanisms

To bypass IP-based rate limits and detection mechanisms, many password spraying tools integrate with proxy services and IP rotation mechanisms.

Proxy Support

Tools such as TREVORspray and SprayingToolkit include robust proxy support. Key features include:

IP Rotation with FireProx

CredMaster and MSOLSpray integrate with FireProx, an AWS-based API gateway that dynamically rotates IP addresses. This integration enables:

Enhanced Detection Evasion Techniques

Password spraying tools incorporate various techniques to evade detection and avoid triggering account lockouts.

Jitter and Delay Configurations

Most tools, including SprayCannon and o365sprayer, support jitter and delay configurations:

Intelligent Lockout Avoidance

Tools like Spray365 and MSOLSpray include features to avoid account lockouts:

Multi-Protocol and Multi-Service Support

Password spraying tools are increasingly versatile, supporting multiple authentication protocols and services.

Microsoft-Specific Protocols

Many tools focus on Microsoft authentication endpoints, including:

Cross-Platform Compatibility

Advanced tools like TREVORspray and SprayCannon extend their capabilities to non-Microsoft protocols, including:

Advanced Logging and Reporting

Comprehensive logging and reporting features are essential for tracking the success of password spraying operations.

Detailed Logs

Tools like TREVORspray and MSOLSpray provide detailed logs, including:

Output Formats

Many tools support exporting results in various formats for further analysis:

Modular Frameworks for Customization

Password spraying tools increasingly adopt modular frameworks, allowing users to customize their functionality.

Custom Modules

Tools like SprayCharles and TREVORspray support custom modules for unique authentication protocols. Examples include:

Template-Based Enumeration

Omnispray provides template modules for enumeration and spraying, enabling users to adapt the tool to various targets.

Execution Plan Templates

Spray365 allows users to create reusable execution plan templates, ensuring consistency across engagements.

Notification and Alerting Capabilities

Some tools include features for real-time notifications and alerts.

Integration with Communication Platforms

SprayCharles supports notifications to platforms like Slack, Discord, and Microsoft Teams. Key features include:

Alerting on Success

Tools like Spray365 and MSOLSpray can pause operations or alert users when valid credentials are identified, reducing unnecessary login attempts.

Reconnaissance and Enumeration Features

Password spraying tools often include reconnaissance capabilities to gather information about target environments.

Domain Reconnaissance

Tools like TREVORspray and o365sprayer perform domain reconnaissance to retrieve:

User Enumeration

Many tools support user enumeration to identify valid usernames before spraying:

Conclusion

This section provided an in-depth exploration of advanced features and capabilities in password spraying tools, focusing on credential management, proxy integration, detection evasion, multi-protocol support, logging, modular frameworks, notifications, and reconnaissance. These features make modern tools highly effective for red team operations targeting Microsoft authentication endpoints and other services.

Detection and Mitigation of Password Spraying Attacks

Advanced Detection Mechanisms in Cloud Environments

Machine Learning-Based Detection

Microsoft Entra ID (formerly Azure AD) employs machine learning (ML) algorithms to detect password spraying attacks. This ML-based detection analyzes patterns across global tenant activity to identify anomalies indicative of password spraying. Unlike heuristic methods, ML-based detection can adapt to new attack patterns, reducing false positives. However, detection delays can range from a few hours to several days, as noted in Microsoft’s documentation. This delay underscores the importance of complementary real-time monitoring.

Sign-In Logs and Error Codes

Sign-in logs in Microsoft Entra ID provide critical insights into failed login attempts. Specific error codes, such as AADSTS50053 (account locked) and AADSTS50126 (invalid password), can indicate password spraying attempts. Organizations can configure Azure Monitor alerts to notify security teams of suspicious activity. These alerts can trigger automated responses, such as account lockouts or IP bans.

Behavioral Analytics

Behavioral analytics tools, such as Microsoft Defender for Cloud Apps (formerly Cloud App Security), analyze user behavior to detect anomalies. For example, a sudden spike in failed login attempts from a single IP address or geographic location can trigger alerts. Behavioral analytics also consider factors like login times and device types to identify potentially compromised accounts.

Custom Detection Rules in SIEMs

Security Information and Event Management (SIEM) platforms like Microsoft Sentinel allow organizations to create custom detection rules. For instance, KQL queries can be used to identify patterns consistent with password spraying, such as multiple failed login attempts across different accounts within a short timeframe. These rules can be tailored to the organization’s specific threat landscape.

Mitigation Strategies for Password Spraying Attacks

Implementing Smart Lockout Policies

Smart lockout policies in Microsoft Entra ID can mitigate password spraying by locking accounts after a predefined number of failed login attempts. Unlike traditional lockout mechanisms, smart lockout differentiates between legitimate users and attackers by analyzing IP addresses and device fingerprints. This feature is particularly effective when combined with FireProx, which attackers use to rotate IP addresses during spraying attempts.

Enforcing Multi-Factor Authentication (MFA)

Multi-Factor Authentication (MFA) significantly reduces the effectiveness of password spraying. Tools like MSOLSpray and o365spray often identify accounts without MFA enabled, making them prime targets. Organizations should enforce MFA for all accounts, including service accounts, to mitigate this risk.

Password Policies and User Education

Strong password policies can thwart password spraying by ensuring that commonly used passwords are not allowed. Tools like Spray365 often exploit weak passwords that meet basic complexity requirements. User education campaigns should emphasize the importance of unique, complex passwords and the risks associated with password reuse.

Geo-Blocking and Conditional Access

Geo-blocking restricts access from regions where the organization does not operate, reducing the attack surface. Conditional access policies in Microsoft Entra ID can enforce additional authentication requirements for high-risk logins, such as those from unfamiliar devices or locations. These policies can be configured to block access entirely or require MFA.

IP Reputation Services

Integrating IP reputation services can help block known malicious IP addresses. For example, TREVORspray uses proxying to evade detection, but IP reputation services can identify and block such proxies. Combining this with real-time threat intelligence feeds enhances the organization’s ability to respond to emerging threats.

Real-Time Monitoring and Alerting

Integration with Security Platforms

Real-time monitoring tools like Microsoft Defender for Identity can detect password spraying attempts by analyzing authentication traffic. These tools integrate with SIEM platforms to provide centralized visibility and alerting.

Automated Incident Response

Automated workflows can be triggered by alerts to contain and mitigate attacks. For instance, when an alert is generated for multiple failed login attempts, the system can automatically disable the affected accounts, block the source IP, and notify the security team. Tools like SprayCannon and CredMaster are designed to evade detection, making automated responses critical.

User Risk Scoring

User risk scoring in Microsoft Entra ID evaluates the likelihood that an account is compromised based on login behavior and other factors. High-risk accounts can be automatically flagged for additional verification or remediation. This feature complements other detection mechanisms by providing a holistic view of account security.

Advanced Threat Hunting Techniques

Analyzing Authentication Patterns

Threat hunters can analyze authentication patterns to identify anomalies indicative of password spraying. For example, a consistent pattern of failed logins followed by a successful login may indicate a compromised account. Tools like DomainPasswordSpray can provide insights into these patterns.

Correlating Events Across Systems

Correlating events across multiple systems, such as email servers and VPN logs, can reveal coordinated attacks. For instance, a successful login to an email account followed by a VPN login from a different location may indicate lateral movement. SIEM platforms like Microsoft Sentinel facilitate this correlation.

Leveraging Threat Intelligence

Threat intelligence feeds can provide information on known malicious IP addresses, domains, and tools. This information can be used to proactively block threats and enhance detection rules. For example, identifying the use of FireProx in authentication traffic can indicate an ongoing password spraying attack.

AI-Driven Detection

Artificial Intelligence (AI) is increasingly being used to detect password spraying attacks. AI models can analyze vast amounts of data to identify subtle patterns that traditional methods might miss. For example, AI can detect low-and-slow attacks, such as those conducted with SprayCharles, which spread login attempts over extended periods.

Zero Trust Architecture

Zero Trust principles, such as continuous authentication and least privilege access, can mitigate the impact of password spraying. By requiring re-authentication for sensitive actions and limiting access based on role, organizations can reduce the risk of compromise.

Integration with Endpoint Detection and Response (EDR)

Integrating password spraying detection with EDR solutions provides a comprehensive view of the attack lifecycle. For instance, detecting a password spraying attempt followed by unusual endpoint activity can indicate a successful compromise.

Advanced Proxy Detection

As tools like TREVORspray and SprayCannon leverage proxying to evade detection, advanced proxy detection techniques are becoming essential. These techniques analyze traffic patterns and metadata to identify malicious proxies.

Enhanced User Awareness

Future mitigation strategies will likely focus on enhancing user awareness through gamified training modules and real-time feedback. For example, users could receive immediate notifications and guidance when their accounts are targeted in password spraying attempts.

This report provides new insights into detection and mitigation strategies for password spraying attacks, emphasizing advanced detection mechanisms, mitigation strategies, real-time monitoring, threat hunting, and emerging trends. It complements existing reports by focusing on actionable measures and future directions, ensuring comprehensive coverage of the topic.

Best Practices for Ethical Use of Password Spraying Tools

Ethical use of password spraying tools must begin with strict adherence to legal and regulatory frameworks. Unauthorized use of these tools can result in severe legal consequences, including violations of computer fraud and abuse laws in various jurisdictions. Ethical practitioners should follow these guidelines:

Minimizing Operational Impact

To avoid disrupting normal business operations, ethical practitioners should implement measures to minimize the impact of password spraying activities:

Secure Handling of Credentials and Data

The ethical use of password spraying tools requires secure handling of sensitive data, including credentials and logs:

Collaboration with Blue Teams

Ethical red teaming should involve collaboration with the organization’s blue team to enhance overall security posture:

Ethical Use of Proxy and IP Rotation Features

Many password spraying tools support proxy integration and IP rotation to evade detection. Ethical practitioners should use these features responsibly:

Advanced Configuration for Ethical Testing

Password spraying tools often include advanced configuration options that can be leveraged for ethical testing:

Continuous Learning and Adaptation

The cybersecurity landscape is constantly evolving, and ethical practitioners must stay updated on the latest tools and techniques:

Ethical Considerations for Multi-Protocol Support

Password spraying tools often support multiple authentication protocols, such as ADFS, OWA, and NTLM. Ethical practitioners should:

Responsible Disclosure and Reporting

After completing a password spraying engagement, ethical practitioners should follow responsible disclosure practices:

By adhering to these best practices, ethical practitioners can ensure that password spraying tools are used responsibly and effectively to enhance organizational security.

Adaptive Spraying Techniques

Adaptive spraying techniques represent a significant evolution in password spraying tools. Unlike traditional methods, which rely on static parameters, these techniques adjust dynamically to the target environment’s defenses. Tools like TREVORspray and Spray365 have introduced adaptive mechanisms that analyze real-time responses from authentication endpoints to modify their spraying behavior. For instance:

This section differs from the previously discussed “Enhanced Detection Evasion Techniques” by focusing on the tools’ ability to adapt in real-time rather than pre-configured evasion strategies.

Integration with Advanced Reconnaissance Tools

Modern password spraying tools are increasingly integrated with reconnaissance tools to enhance their effectiveness. For example, DomainPasswordSpray can automatically generate a user list from the domain, while TREVORspray supports domain reconnaissance as a standalone feature. Key advancements include:

This section expands on the reconnaissance capabilities mentioned in previous reports by emphasizing the integration of external tools and APIs.

Advanced Multi-Stage Spraying Workflows

Password spraying tools are now incorporating multi-stage workflows to bypass sophisticated defenses. For instance, Spray365 introduces execution plans that define multiple stages of spraying, each with unique parameters. Features include:

This section builds on the “Advanced Credential Management and Execution Plans” discussed earlier by focusing on multi-stage workflows rather than single-stage execution plans.

AI and Machine Learning Integration

The integration of AI and machine learning is emerging as a game-changer in password spraying. While defenders have long used these technologies for detection, attackers are now leveraging them to enhance their tools. Examples include:

This section introduces a novel perspective not covered in previous reports, focusing on the offensive use of AI and machine learning.

Targeted Spraying for Specific Roles

Targeted spraying focuses on high-value accounts, such as administrators or executives, rather than indiscriminately attacking all users. Tools like SharpSpray and Go365 are particularly effective for this purpose. Features include:

This section complements the “Reconnaissance and Enumeration Features” by focusing on role-specific targeting rather than general user enumeration.

Hybrid Authentication Protocol Attacks

Hybrid attacks combine multiple authentication protocols to increase the likelihood of success. For example, TREVORspray supports protocols like MSOL, ADFS, and OWA, allowing attackers to target multiple endpoints simultaneously. Key features include:

This section expands on “Multi-Protocol and Multi-Service Support” by highlighting the strategic use of multiple protocols in a single operation.

Real-Time Collaboration Features

Some tools now include features for real-time collaboration among red team members. For instance, TREVORspray logs all activities to shared files, enabling team members to coordinate their efforts. Features include:

This section introduces a new dimension of teamwork and collaboration not previously discussed.

Advanced Proxy and Anonymization Techniques

While proxy support has been a standard feature, advanced anonymization techniques are now being integrated into tools like TREVORspray and MSOLSpray. These include:

This section builds on “Integration with Proxy and IP Rotation Mechanisms” by focusing on cutting-edge anonymization techniques.

Enhanced Reporting and Visualization

Modern tools are incorporating advanced reporting features to provide actionable insights. For example, Spray365 offers detailed JSON reports that can be imported into SIEMs for further analysis. Features include:

This section complements “Advanced Logging and Reporting” by emphasizing visualization and customization.

Future-Proofing Against Detection Mechanisms

As detection mechanisms evolve, tools are incorporating features to future-proof their operations. Examples include:

This section introduces forward-looking strategies not covered in existing reports.

Integration with Cloud-Native Environments

With the increasing adoption of cloud services, tools are being optimized for cloud-native environments. For instance, MSOLSpray and o365spray are specifically designed for Microsoft Azure and Office 365. Features include:

This section builds on “Advanced Features in Password Spraying Tools for Microsoft Authentication Endpoints” by focusing on cloud-specific optimizations.

Ethical Implications of Advanced Features

The ethical use of advanced features in password spraying tools is a growing concern. For example:

This section complements “Best Practices for Ethical Use of Password Spraying Tools” by focusing on the ethical implications of advanced features.

Continuous Development and Community Contributions

The open-source nature of most password spraying tools allows for continuous development and community contributions. For example:

This section highlights the role of the community in advancing password spraying techniques, a topic not previously covered.

Conclusion

This research highlights the top 10 most starred password spraying tools on GitHub, emphasizing their relevance to Red Team operations targeting Microsoft authentication endpoints such as Office 365 and Azure Active Directory. Password spraying, a technique that tests a single password across multiple accounts to evade lockout mechanisms, remains a critical tactic for assessing organizational defenses. Tools like SprayingToolkit, DomainPasswordSpray, and o365spray stand out for their advanced features, including modular frameworks, proxy integration, and detailed logging, which enhance their effectiveness and adaptability. The integration of capabilities such as IP rotation via FireProx, multi-protocol support, and real-time detection evasion underscores the sophistication of these tools in simulating real-world attack scenarios.

The findings underscore the growing complexity of password spraying tools, which now incorporate advanced features like dynamic credential rotation, adaptive workflows, and integration with reconnaissance tools. These advancements not only improve operational efficiency but also challenge traditional detection mechanisms. However, the ethical use of these tools remains paramount. Organizations must ensure proper authorization, adherence to scope, and secure handling of sensitive data during engagements. The research also highlights the importance of collaboration between Red and Blue Teams, leveraging insights from password spraying simulations to strengthen defenses and improve detection capabilities.

Looking ahead, the implications of emerging trends such as AI-driven password prediction, hybrid authentication protocol attacks, and cloud-native optimizations are significant. These developments demand continuous updates to defensive strategies, including enhanced monitoring, behavioral analytics, and proactive mitigation measures like enforcing multi-factor authentication (MFA) and implementing smart lockout policies. As password spraying tools evolve, organizations must adopt a proactive, layered security approach to mitigate risks and stay ahead of adversaries.

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