Certified: The Security+ Prepcast

When an organization brings on a vendor, the risk management process does not stop at contract signing. It is only just beginning. Security is not static—and neither are the vendors you depend on. Systems evolve, personnel change, and new threats emerge. That is why vendor monitoring and continuous evaluation are vital parts of an effective security program. In this episode, we will explore three key practices that help organizations maintain strong vendor oversight: ongoing vendor monitoring, the use of security questionnaires, and establishing clear rules of engagement for vendor assessments.
Let’s begin with ongoing vendor monitoring. This refers to the continuous or periodic observation and evaluation of a vendor’s security practices, risk exposure, and compliance status. The goal is to ensure that vendors remain in alignment with your security requirements and contractual obligations—not just at the beginning of the relationship, but for as long as the partnership continues.
Ongoing monitoring can take several forms. It may include regular reviews of security controls, audits of access logs, alerts from threat intelligence feeds, or scheduled check-ins to review compliance reports. Many organizations use vendor scorecards to track key metrics such as incident frequency, system uptime, or compliance status. Others deploy third-party risk monitoring platforms that scan the internet and dark web for signs of breach, exposed credentials, or poor patch management linked to vendor domains.
Monitoring also includes staying aware of changes that may affect vendor risk. Has the vendor merged with another company? Have there been major staff changes, layoffs, or public breaches? These events can impact service delivery and security posture. Ongoing monitoring provides the visibility needed to spot red flags and intervene before issues escalate.
Let’s consider a real-world example. A regional bank uses a cloud-based analytics platform managed by a third-party vendor. As part of its vendor monitoring process, the bank subscribes to a third-party monitoring service that tracks public breach disclosures and changes in certificate management. One day, the system alerts the bank that the vendor has failed to renew a Transport Layer Security certificate, creating a brief exposure window. The bank contacts the vendor, who immediately resolves the issue. Thanks to real-time monitoring, a potentially serious incident is detected and contained before any customer data is compromised.
Ongoing monitoring builds accountability into the relationship. Vendors are more likely to maintain strong security when they know their performance is being observed. It also supports compliance. Many regulatory frameworks, such as the Health Insurance Portability and Accountability Act or the Payment Card Industry Data Security Standard, require proof that third-party risk is being monitored on an ongoing basis.
Next, let’s talk about vendor questionnaires. A vendor questionnaire is a structured set of questions sent to vendors to gather detailed information about their security policies, practices, and posture. Questionnaires are a core component of due diligence and are also used throughout the lifecycle of a vendor relationship to confirm that standards are being maintained.
A good questionnaire covers areas like access control, encryption practices, data retention policies, incident response procedures, employee training, and regulatory compliance. Questions may be formatted as multiple-choice, yes-or-no, or open-ended. Some organizations develop their own internal questionnaire templates, while others use standardized tools such as the Consensus Assessments Initiative Questionnaire or the Standardized Information Gathering questionnaire.
The value of a questionnaire lies in its ability to capture structured, comparable data from multiple vendors. This makes it easier to score, track, and analyze risk consistently. When combined with other sources—such as penetration test results or audit reports—the questionnaire creates a fuller picture of vendor security.
Let’s look at a practical scenario. A healthcare provider is preparing for an expansion into telemedicine. As part of its vendor onboarding process, it sends security questionnaires to three video conferencing platform vendors. The questionnaire includes questions about data encryption, multi-factor authentication, data residency, and past breach disclosures. One vendor fails to answer several critical questions and provides vague responses. Another submits detailed answers with links to third-party audits and internal policy documents. The provider selects the more transparent vendor, reducing potential legal and privacy risks. In this case, the questionnaire helped uncover gaps that were not obvious during sales pitches or demos.
Questionnaires are not just for onboarding. They can also be used annually or during major policy updates. For example, if your organization rolls out a new password policy or changes its data retention standards, you may need to verify whether key vendors are aligned. A follow-up questionnaire can close that loop and confirm compliance.
It is important to recognize the limitations of questionnaires. Some vendors may provide incomplete, outdated, or overly optimistic answers. That is why questionnaires should not be your only assessment tool. Combine them with audits, monitoring, and contractual controls for best results.
Finally, let’s discuss rules of engagement. Rules of engagement are the clearly defined procedures, scope, and boundaries that guide any formal assessment or test of a vendor’s system. This includes activities like penetration testing, system monitoring, or vulnerability scanning. Rules of engagement ensure that security assessments are conducted legally, ethically, and safely—without disrupting the vendor’s operations or violating contract terms.
Before conducting any direct testing of a vendor’s environment, organizations must receive written permission. This usually takes the form of an assessment agreement or is included in the vendor’s contract. The rules of engagement spell out exactly what systems are in scope, what tools will be used, when the testing will occur, who will be notified, and how results will be reported and protected.
Without clear rules of engagement, assessments can go wrong quickly. Unauthorized testing may violate service terms or even legal regulations. Poorly scoped tests may take down production systems, leak sensitive data, or create mistrust between partners. That is why planning, coordination, and communication are critical.
Let’s walk through a case study. A global logistics company is preparing to perform a penetration test on its supplier portal, which is hosted and maintained by an external vendor. Before launching the test, the company meets with the vendor to define the rules of engagement. Together, they agree that only staging systems will be tested, that no denial-of-service techniques will be used, and that results will be shared in a redacted report within seven days. Both sides sign off, and the test is completed without disruption. Because the rules were clearly defined in advance, the assessment strengthens security and trust.
Rules of engagement are also important for internal communication. Legal teams, risk managers, and executives should be aware of any testing activity involving vendor systems. A documented process—along with change control logs and security briefings—helps prevent surprises and reduces liability.
As you study for the Security Plus exam, make sure you understand the role of each tool discussed today. Ongoing monitoring tracks vendor performance over time. Questionnaires collect structured data on vendor security posture. And rules of engagement define how formal assessments are safely conducted. Expect to see scenario-based questions that ask which method is most appropriate based on timing, scope, or the type of information being gathered.
Here’s a quick tip. If the question describes watching for changes in real time or over months, the answer points to vendor monitoring. If it involves asking structured questions about policies or controls, it’s about vendor questionnaires. And if it discusses permissions, assessment scope, or test planning, it’s clearly referencing rules of engagement. Watch for those contextual clues—they make all the difference.
To access sample vendor questionnaires, rules of engagement templates, and monitoring tool reviews, visit us at Bare Metal Cyber dot com. And for the most complete and efficient Security Plus study experience, go to Cyber Author dot me and order your copy of Achieve CompTIA Security Plus S Y Zero Dash Seven Zero One Exam Success.