Understanding Technical Debt Part 2: Real Scenarios in Cybersecurity

Scenario 1 - SASE

A global manufacturing company adopts a SASE framework to modernize its cybersecurity posture, driven by the need to secure remote workers and streamline access to cloud applications. Initially, the company quickly deployed SASE components, including SD-WAN and CASB (Cloud Access Security Broker), to meet pandemic-driven remote work demands. However, the implementation was rushed, leaving critical elements incomplete.

Over time, as new locations, cloud services, and users were added, the company's SASE environment began to show cracks due to the shortcuts taken during the initial deployment.

The technical debt

1. Incomplete Zero Trust implementation
   The company adopted SASE for its promise of zero trust, but the IT team configured overly permissive access policies due to time constraints. Many remote workers were granted broad access to internal systems without proper user or device verification.
2. Unoptimized traffic routing
   The SD-WAN component was configured with static routing rules during the initial rollout. As the network grew, these rules created inefficiencies, leading to latency for critical applications like CAD software hosted in the cloud.
3. Legacy VPN coexistence
   The IT team maintained legacy VPNs alongside the SASE solution to avoid disrupting existing workflows. This created overlapping systems, with some employees bypassing SASE controls entirely using the old VPN.
4. Lack of centralized policy management
   The SASE framework was deployed piecemeal, with different teams managing separate CASB, SD-WAN, and secure web gateway (SWG) policies. This siloed approach led to inconsistent enforcement of security policies across the environment.

The consequences

1. Data leakage
   Due to the weak implementation of CASB policies, sensitive manufacturing blueprints were accessed and downloaded by a contractor whose permissions had yet to be reviewed or restricted.
2. Increased security risks
   Overly permissive access policies allowed a compromised remote worker's device to spread malware into the corporate network, disrupting operations at several manufacturing sites.
3. Operational inefficiencies
   Static SD-WAN routing led to complaints about slow application performance, particularly during peak working hours, reducing employee productivity.
4. High management costs
   Managing overlapping systems (SASE and legacy VPNs) and siloed security policies required excessive manual effort from the IT team, delaying response times to threats and increasing operational costs.

How it could have been avoided

1. Phased rollout with proper testing
   Instead of simultaneously deploying all components, the company could have adopted a phased approach, testing each SASE component thoroughly and optimizing policies before expanding.
2. Centralized policy management
   SASE's integrated management capabilities would have ensured consistent security enforcement across CASB, SD-WAN, and SWG components, reducing siloed operations.
3. Dynamic access policies
   A proper zero-trust framework, with dynamic access policies based on user identity, device posture, and real-time risk assessments, should have been implemented from the start.
4. Decommissioning Legacy VPNs
   Retiring legacy VPNs would have eliminated conflicting systems and forced all traffic through the SASE framework, improving security and visibility.

Key takeaway

This example illustrates how technical debt in SASE adoption can undermine the very benefits it promises. SASE is designed to simplify and enhance security, but shortcuts during implementation create vulnerabilities, inefficiencies, and management challenges. Addressing technical debt proactively—through phased rollouts, centralized management, and proper policy design—ensures SASE delivers on its potential to secure and optimize modern networks.

Scenario 2 – SSL decryption

A financial services company implemented SSL decryption to enhance its security posture by inspecting encrypted traffic for threats like malware and data exfiltration. However, due to tight deadlines and limited resources, the initial deployment of SSL decryption was only partially configured, leading to significant technical debt over time.

The organization relied on a legacy NGFW (Next-Generation Firewall) for SSL decryption but skipped key optimizations to meet immediate compliance requirements.

The technical debt

1. Partial SSL traffic inspection
   The NGFW was configured to decrypt and inspect traffic for only a few critical applications. Other traffic, including traffic to lesser-known cloud services and some employee devices, was allowed to bypass inspection entirely.
2. Outdated cipher support
   The SSL decryption engine was never updated to support modern encryption protocols like TLS 1.3. As a result, it could only decrypt older protocols (e.g., TLS 1.1), leaving a growing portion of encrypted traffic uninspected as applications and services adopted more robust encryption.
3. Performance bottlenecks
   The initial hardware needed more resources to handle the increasing volume of encrypted traffic efficiently. This led to latency issues and employee complaints about slow application performance, prompting IT to disable decryption for specific traffic as a quick fix.
4. Inconsistent policy enforcement
   Different IT teams managed decryption policies across various tools (e.g., firewalls, proxies). This fragmented approach caused security gaps, with some traffic inspected and other traffic bypassing checks entirely.

The consequences

1. Undetected malware
   An attacker leveraged an encrypted channel to deliver malware that went undetected by the firewall. The malware spread across the network, causing a significant breach that impacted customer data.
2. Regulatory non-compliance
   The company failed an audit for PCI-DSS compliance because encrypted payment traffic was not consistently inspected for potential threats, resulting in fines and reputational damage.
3. Operational inefficiencies
   Decryption-related performance bottlenecks led to frequent complaints from employees and IT staff. Over time, this eroded trust in the security tools and discouraged teams from enabling SSL inspection.
4. Increased risk of shadow IT
   By failing to inspect all encrypted traffic, the company allowed unapproved SaaS tools and external cloud services to proliferate, further increasing exposure to potential threats.

How it could have been avoided

1. Upgrading hardware
   Investing in decryption-capable hardware during the initial deployment would have ensured the system could handle high traffic volumes without degrading performance.
2. Expanding protocol support
   Updating the decryption engine to support modern encryption protocols (like TLS 1.3) would have kept the inspection process effective as encryption standards evolved.
3. Centralized policy management
   Implementing a centralized platform to manage SSL decryption policies would have ensured consistent inspection across all tools and traffic types.
4. Regular audits and optimization
   Periodic audits of SSL decryption policies and performance metrics would have identified gaps, outdated configurations and bottlenecks, enabling proactive fixes.

Key takeaway

This example highlights how technical debt in SSL decryption can leave critical blind spots in cybersecurity defenses. While SSL decryption is essential for protecting against encrypted threats, it requires consistent updates, adequate hardware, and centralized policy enforcement. Ignoring these areas creates vulnerabilities attackers can exploit, undermining the organization's security posture and compliance efforts.

Scenario 3 – NGFW Rule Management

A national retail chain implemented a Next-Generation Firewall (NGFW) to protect its network, which includes corporate offices, point-of-sale (POS) systems, and e-commerce operations. Initially, the firewall was configured with basic rules to meet tight deployment deadlines.

Over the years, different IT teams have added rules ad hoc to address urgent needs, such as granting temporary access to third-party vendors or troubleshooting network issues. However, these changes were poorly documented, rarely reviewed, and never optimized.

The technical debt

1. Overlapping and redundant rules
   The NGFW's policy now includes thousands of rules, many of which are redundant or conflict with each other. For example, a rule allowing temporary vendor access to sensitive segments was never removed after the vendor's contract ended.
2. Lack of segmentation
   To meet operational demands quickly, the initial configuration skipped proper segmentation. For instance, POS systems, corporate servers, and guest Wi-Fi all share overlapping network access policies. This creates unnecessary risk.
3. Outdated rules
   Some rules reference old IP ranges or services no longer in use. These "orphaned rules" clutter the policy, increasing the likelihood of human error when troubleshooting or adding new rules.
4. Performance issues
   The large and inefficient rule set degrades NGFW performance, slowing traffic inspection and delaying threat detection.

The Consequences

1. Increased risk of a data breach
   An attacker exploited a forgotten rule granting broad access to the retail chain's database servers. This allowed them to exfiltrate sensitive customer payment data.
2. Failure to detect threats
   With too many conflicting or redundant rules, critical alerts were missed during an advanced persistent threat (APT) attack. The NGFW was overwhelmed with unnecessary logs, hiding real threats in the noise.
3. Compliance violations
   The company was found non-compliant with PCI-DSS requirements due to inadequate segmentation of cardholder data environments from other network traffic. This resulted in regulatory fines.
4. High maintenance costs
   Troubleshooting firewall issues became a time-consuming nightmare for the IT team. Every change risked breaking something because of the tangled web of policies, slowing business operations and increasing costs.

How it could have been avoided

1. Regular rule audits
   Periodic reviews of NGFW rules could have identified and removed redundant, outdated, or unnecessary policies. Tools that analyze and optimize firewall rules could have streamlined this process.
2. Proper network segmentation
   From the start, the company should have implemented precise segmentation between POS systems, corporate servers, and other environments, ensuring that only necessary traffic flows between them.
3. Adherence to best practices
   Following NGFW best practices, such as least privilege access and automated rule expiration for temporary access, would have reduced the buildup of technical debt.
4. Automation and monitoring
   Using automation tools to manage rule sets and monitor compliance would have ensured consistent application of security policies and reduced manual errors.

Key takeaway

This example demonstrates how technical debt in NGFW management can lead to significant cybersecurity risks. While NGFWs are powerful tools, their effectiveness depends on proper configuration, regular maintenance, and adherence to security best practices. Ignoring this creates vulnerabilities that attackers can exploit, turning a sophisticated security tool into a liability.

Scenario 4 – automation in cybersecurity

A mid-sized healthcare organization implemented a vulnerability management program using an automation tool. Initially, the tool was configured to automatically scan the network, identify vulnerabilities, and generate remediation tickets. However, the initial implementation was rushed due to tight deadlines and limited resources, and shortcuts were taken to meet compliance requirements.

Over the years, the vulnerability management tool's automation workflows were not updated to account for these changes as the organization's IT infrastructure grew (e.g., adding cloud services, IoT medical devices, and remote work environments). Additionally, the IT team relied on quick patches and manual overrides rather than overhauling the automation logic.

The technical debt

1. Outdated scan configurations
   The automation tool still scans legacy on-premise systems but doesn't include newer cloud infrastructure, IoT devices, or external-facing APIs. This blind spot leaves critical vulnerabilities undetected.
2. Overloaded ticketing system
   The automation generates remediation tickets for every vulnerability, regardless of severity. Without prioritization logic, the IT team is overwhelmed with low-risk issues, leaving critical vulnerabilities unresolved.
3. Fragmented processes
   Automation workflows were designed for a static network but failed to account for dynamic changes in modern IT environments, such as temporary cloud workloads. This results in broken processes and missed vulnerabilities.
4. Security tool sprawl
   Instead of integrating the automation tool with other security systems (e.g., SIEM, SOAR or endpoint protection platforms), the team relies on siloed tools that don't communicate. This lack of integration adds manual work and delays responses.

The consequences

1. Unpatched critical vulnerabilities
   Attackers exploited an unmonitored cloud server to deploy ransomware, crippling critical healthcare operations and exposing patient data.
2. Regulatory fines
   The organization was fined for non-compliance with HIPAA due to the failure to manage vulnerabilities in protected systems.
3. Burnout and turnover
   The IT team struggled to manage the flood of tickets generated by the automation tool. High-priority vulnerabilities were buried under false positives and low-risk findings, leading to frustration and employee turnover.
4. Loss of trust
   The breach resulted in public scrutiny and loss of patient trust, significantly impacting the organization's reputation and revenue.

How it could have been avoided

1. Dynamic automation updates
   Automation workflows should be updated regularly to reflect changes in the IT environment. For example, rules can be added to include cloud, IoT, and remote assets in vulnerability scans.
2. Risk-based prioritization
   Instead of treating all vulnerabilities equally, the automation should incorporate severity scoring (e.g., CVSS) and business context to prioritize critical vulnerabilities over minor issues.
3. Integration with the security ecosystem
   The automation tool should have been integrated with a SIEM or SOAR platform to correlate vulnerabilities with real-time threats and streamline response efforts.
4. Regular audits and optimization
   Periodic reviews of the automation logic could have identified inefficiencies and blind spots, ensuring the system evolves with the organization's needs.

Key takeaway

This example highlights how technical debt in cybersecurity automation can transform a helpful tool into a liability. Automation is only as effective as its configuration and maintenance. Neglecting updates, optimization and integration creates gaps that attackers can exploit, resulting in more significant costs, risks, and operational challenges. Proactively managing this debt ensures that automation delivers on its promise of efficiency and security.

Scenario 5 – an AWS buildout

A growing e-commerce company migrated its infrastructure to AWS to scale operations quickly and use cloud-native tools. The initial deployment included multiple AWS services, such as EC2 instances for hosting applications, S3 buckets for storage, and a VPC (Virtual Private Cloud) for network segmentation.

Due to tight deadlines, the company's DevOps team prioritized functionality over security. While the environment worked well initially, the shortcuts taken to speed up deployment created technical debt that led to significant cybersecurity challenges down the line.

The technical debt

1. Overly permissive IAM roles
   During deployment, the team assigned overly broad permissions to IAM (Identity and Access Management) roles to "get things working." For example, a role for application servers was granted full access to all S3 buckets instead of limiting access to specific buckets.
2. Misconfigured S3 buckets
   S3 buckets were configured with public access to facilitate quick testing during development. These settings were never updated for production use, exposing sensitive customer data to the internet.
3. Inadequate security groups
   The security groups associated with EC2 instances were set with overly broad inbound and outbound rules (e.g., allowing SSH from any IP address). These were never locked down after the initial setup.
4. No logging or monitoring
   AWS CloudTrail and GuardDuty were not enabled due to concerns about cost and complexity. As a result, there was no visibility into access logs or unusual activity in the environment.

The consequences

1. Data breach
   An attacker exploited a publicly accessible S3 bucket containing customer data. The breach leaked sensitive information, damaging customer trust and triggering regulatory investigations.
2. Unauthorized access
   Using the overly permissive IAM roles, an attacker accessed critical application resources and injected malicious code, disrupting e-commerce operations.
3. Missed threat detection
   Without CloudTrail and GuardDuty, the team failed to detect and respond to the attacker's activity in real time, allowing the breach to go unnoticed for weeks.
4. Regulatory non-compliance
   The company faced fines for failing to comply with GDPR and other data protection regulations due to poor access control and a lack of visibility into security events.

How it could have been avoided

1. Principle of least privilege for IAM roles
   Assigning specific, minimal permissions to IAM roles from the start would have reduced the risk of unauthorized access to resources.
2. Secure S3 configurations
   Using AWS's built-in tools, such as bucket policies and access analyzer, would have ensured that S3 buckets were not publicly accessible unless absolutely necessary.
3. Hardened security groups
   Implementing strict inbound and outbound rules for security groups (e.g., allowing SSH only from known IPs) would have minimized exposure to unauthorized access.
4. Enable logging and monitoring
   Enabling AWS CloudTrail, GuardDuty, and VPC Flow Logs from day one would have provided the visibility needed to detect and respond to threats promptly.
5. Automated compliance checks
   Using AWS Config to enforce compliance with security best practices and regularly scanning the environment for misconfigurations would have prevented technical debt from accumulating.

Key takeaway

This example demonstrates how technical debt in building AWS environments can lead to critical vulnerabilities. While speed and flexibility are key advantages of the cloud, ignoring security best practices during initial deployment creates significant risks. A proactive approach to securing AWS environments—through proper configurations, least privilege and monitoring—can prevent costly breaches and operational disruptions down the line.

Conclusion: turning technical debt into a strategic advantage

As we've seen throughout this article, technical debt in cybersecurity is more than just an IT headache—it's a business risk with far-reaching consequences. Whether it's a poorly configured Next-Generation Firewall, unsecured cloud environments in AWS, or outdated SSL decryption policies, the cost of ignoring technical debt can include breaches, operational disruptions, regulatory fines, and reputational damage.

Yet, technical debt isn't inherently bad. Sometimes, it's a necessary trade-off to meet pressing business needs or deliver faster results. The key lies in acknowledging its existence, understanding its implications, and managing it proactively. By applying regular audits, following best practices, and integrating security into every stage of your IT processes, you can minimize the risks and build a resilient cybersecurity framework.

Technical debt is inevitable, but its impact is not. With a proactive approach and a commitment to continuous improvement, organizations can transform technical debt from a liability into an opportunity to strengthen their security posture, innovate more effectively, and stay ahead in a dynamic threat landscape. The examples in this article serve as a reminder that managing technical debt today is an investment in a more secure tomorrow.

Coming Soon:  The next Grizzled Cyber Vet series trilogy will compare and contrast a 'Ford vs. Chevy' debate relative to cybersecurity's platform play vs. point solutions.