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Have you ever been in the middle of an incident response and realized you can’t get to the root of the problem, simply because the key logs of events are missing? This issue is known as Security Logging and Monitoring Failures in the OWASP list of security risks. 

Such gaps in visibility make it easy for attackers to exploit vulnerabilities and move laterally across systems without being detected.  

This blog covers the risks, causes, real-world examples, and best practices for preventing security logging and monitoring failures.

What Are Security Logging And Monitoring Failures?

Security logging and monitoring is the process of recording events that happen within your IT environment and analyzing them to spot potential threats. When this process fails, it creates blind spots that attackers can exploit. 

These failures are a significant security risk, often enabling breaches to go unnoticed for a long time. For instance, the failure to log repeated failed login attempts may allow hackers to gain unauthorized access in your cloud environment.

Why Security And Monitoring Failures Matter

Strong logging and monitoring mechanisms can help spot issues early. Additionally, they are also crucial for regulatory compliances: 

  • PCI DSS v4.0: Requires recording every access to sensitive systems and cardholder data, securing logs, reviewing them daily, and keeping them for at least one year.
  • HIPAA Security Rule: Mandates audit controls to track and review activity around electronic protected health information.
  • SOC 2: Calls for anomaly monitoring and detailed audit trails to identify and address security incidents promptly.

Common Causes of Security Logging And Monitoring Failure

Security logging and monitoring failures occur due to multiple reasons, such as:

Missing Auditable Events

Logging records events like failed login attempts, but thresholds determine how these events trigger alerts. If a breach occurs and login attempts are not documented, how will security experts follow the attacker’s path? 

In the Target data breach incident in 2013, merely maintaining logs of failed login attempts had helped in timely detection of the issue. But this seemingly small mistake allowed hackers to enter the system and steal data of millions of customers.

Inadequate Warning Messages

Incomplete or vague error messages indicate a lack of clear information in the security logs and alerts generated by the system. This delays the response. 

For example, a generic message alert like “Error occurred” can leave security professionals guessing. 

Is it a failed login? A system glitch? Or, a possible attack? On the other hand, a message like “Failed login attempt detected from IP 192.168.X.X” gives a clear direction. 

Clear error messages allow security teams to investigate, block suspicious traffic, and limit the risk without losing valuable time if events are properly logged. 

Unmonitored Applications Logs 

Ignoring application logs can hide severe cyberattacks, such as SQL injection. If there are repeated failed database queries and logs are left unmonitored; it may hide the cyberattack and the threat will remain undetected without monitoring. 

Local Log Storage Only

Many companies only store logs on local systems, but this risks data loss during cyber breaches or hardware failures. A centralized logging mechanism helps ensure logs are securely maintained which is vital for incident response and compliance. 

Ineffective Alerting Thresholds

Logging records of events like failed login attempts, but thresholds directly impact how these logged security events trigger alerts. If the threshold alert limit is set too low, it triggers many false positives, overwhelming teams. If it’s set too high, real threats may be missed. 

Properly configured thresholds balance alert accuracy and noise, helping security teams quickly identify real dangers without getting distracted by irrelevant alerts. Regular tuning is essential. 

For example, if your threshold limit has been set to 100 failed logins before alerting, it may let attackers brute force attacks go undetected. 

Insufficient Logging

Many companies record only error logs, often ignoring user actions that add context. This lack of detail limits security teams’ visibility. This lack of detailed logging obstructs the visibility of security teams. 

For example, failing to log file access attempts makes it hard to trace unauthorized data access, hindering investigations and leaving systems vulnerable to insider threats or external breaches.

Weak Monitoring Systems

Using outdated tools may miss advanced threats. For example, a legacy system may not detect a zero-day exploit, leaving the network vulnerable to attacks. 

Lack of Integrity in Logs

Unprotected logs can be altered or deleted. For example, an attacker modifying logs to remove evidence of their activities undermines forensic investigations, making it difficult to understand the data breach scope and implement effective countermeasures. to limit its impact.

Compliance Violations

Failing to log may lead to violation of data breaches regulations. For example, not logging access to sensitive health data violates HIPAA, leading to fines, legal consequences, and reputational damage, emphasizing the need for comprehensive logging practices.

Large Logs Volume

When systems log excessively without proper filtering or analysis tools, this becomes meaningless as critical threats can be buried in the noise. For example, analyzing millions of logs daily will not be possible for security teams and incidents like brute-force attacks may go unnoticed. It underscores the need for efficient log management.

Insecure Logging Systems

Logs stored without encryption can be potentially vulnerable to interception or tampering. For example, an attacker can intercept unencrypted logs that might contain sensitive information, such as user credentials or credit card details. 

It emphasizes secure logging practices, such as encryption, access controls, and integrity checks for log data protection.

Real -World Examples of Logging Failures

Example # 1: Microsoft’s Cloud Logging Mess, 2024

In early September 2024, Microsoft experienced a serious issue with its cloud logging mechanism. A bug in its internal monitoring agents disrupted its log data collection of key services like Microsoft Sentinel and Microsoft Entra. 

For nearly three weeks, logs were inconsistent, creating blind spots for customers relying on them for threat detection and investigation. This was due to the failure of recording and monitoring key logged data.

Example #2: Cloudflare’s Log Blackout, 2024

On November 14, 2024, Cloudflare experienced a major outage in its logging pipeline. A misconfiguration resulted in a cascading failure that wiped out approximately 55% of customer logs over a three-and-a-half-hour window. This sudden loss of logged data means security teams could not timely detect suspicious activities.  

Such incidents underscore just how weak a logging system can be, and why a robust log monitoring mechanism matters to security and compliance.

  • CWE-117: Improper Output Neutralization for Logs occurs when log entries fail to properly sanitize user-controlled inputs. 
  • CWE-223: Omission of Security-relevant Information occurs when events are  logged without enough context, such as without details like timestamps, source IPs, or error codes. 
  • CWE-532: Insertion of Sensitive Information into Log File occurs when sensitive data such as passwords, tokens, or personal identifiers are mistakenly logged.  
  • CWE-778: Insufficient Logging occurs when security-relevant actions are not logged at all.

Best Practices for Security Logging And Monitoring Failures

Secure Log Data

  • Implement SHA-256 hashing for log file integrity verification with hourly checksums stored separately.
  • Use role-based access control (RBAC) mechanism to limit access to raw logs.

Establish Effective Monitoring

  • Configure alerts for specific thresholds. 
  • Set up real-time monitoring dashboards that show authentication failures, System errors, Suspicious file access patterns. 

Establish Incident Response Plan

  • Define clear escalation paths with contact information for each severity level (e.g., Level 1: SOC analyst, Level 2: Security Manager, Level 3: CISO). 
  • Create detailed playbooks for common incidents including exact commands and procedures (e.g., steps to isolate compromised systems, evidence collection procedures). 

Develop a Logging and Monitoring Plan

  • Identify and log all critical data across systems, including user activities, system events, and security incidents to ensure thorough monitoring.
  • Establish clear retention periods for different log types based on regulatory requirements. 
  • Utilize centralized storage solutions, such as data lakes or cloud-based services, to manage log data effectively. 

Ensure Proper Configuration

  • Regularly review logging configurations to ensure all necessary data is captured. 
  • Implement structured logging formats (e.g., JSON) to facilitate easier parsing and log data analysis.
  • Continuously update monitoring tools and configurations to ensure optimal performance. 

Log Crucial Activities

  • Implement a comprehensive logging framework that includes access to sensitive data, and changes to user permissions. 
  • Capture all login attempts, both successful and failed, alongside relevant metadata, such as timestamps, user IDs, and IP addresses. 
  • Document security incidents meticulously, including details of unauthorized access attempts or anomalies in system behavior, to support forensic investigations.

Closing Thoughts

Most logging and monitoring failures occur because logging processes are not structured and lack appropriate context. Therefore, maintaining audit logs and monitoring is a critical step to security as it can reveal the path traversed by threat actors. This helps security teams understand attack strategy and they can improve incident response planning. 

Ignoring OWASP security vulnerabilities can be risky for organizations. Our penetration testing experts can help. Contact us now to learn more.

Frequently Asked Questions

What are common examples of A09 logging and monitoring failures?

Common examples include not logging failed logins, privilege escalation attempts,  inconsistent log formats, and short or non-compliant log retention. 

Why should leadership care about this?

They should care because this failure directly impacts the bottom line. Undetected breaches lead to greater financial losses,and regulatory fines for non-compliance. 

What’s the real-world business impact?

The impact is delayed breach detection. This allows attackers weeks or months to steal sensitive customer data or intellectual property. 

Reference resources: 

A09 Security Logging and Monitoring Failures – OWASP Top 10

Effective-Daily-Log-Monitoring-Guidance.pdf   

Validating CloudTrail log file integrity – AWS CloudTrail

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