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TEC-CYBE44-03 · Lesson 5 · 14 clock hours · lab

PKI and Certificate Management Lab

Objective. Students will generate a certificate signing request (CSR), issue a certificate from a lab certificate authority (CA), install it on a test web server, and verify the trust chain.

⚠ Pending professional review

This lesson, its worked examples and its practice questions has not yet been verified by an industry-certified professional or by a certification or approval body. It is a study draft and may contain errors. Do not use it as instructions for work on a job site or on live equipment. Always follow your instructor, your supervising professional, and current official references and regulations.

VoTechWorks program approval and accreditation are still in progress. Credentials are issued only by the certifying bodies named in each program, after their own exams.

What Is a Public Key Infrastructure?

A Public Key Infrastructure (PKI) is the framework of policies, hardware, software, and procedures that creates, manages, distributes, stores, and revokes digital certificates. At its core, PKI lets two parties who have never met verify each other's identities using cryptography. When you visit a website secured with HTTPS, PKI is working behind the scenes to guarantee that the server is who it claims to be and that your connection is encrypted.

The central component of PKI is the Certificate Authority (CA). A CA is a trusted entity that signs digital certificates, vouching for the identity of the certificate holder. Browsers and operating systems ship with a built-in list of trusted root CAs. Any certificate signed by one of those root CAs — directly or through an intermediate CA — is automatically trusted.

How Certificates Are Issued: The CSR Workflow

Issuing a certificate follows a defined sequence:

1. Generate a private key. The server owner creates an asymmetric key pair. The private key never leaves the server.

2. Create a Certificate Signing Request (CSR). A CSR is a file containing the server's public key plus identifying information: Common Name (CN), Organization (O), Organizational Unit (OU), Country (C), and the Subject Alternative Names (SANs) for modern certificates. The private key signs the CSR so the CA can confirm the requester controls it.

3. Submit the CSR to the CA. The CA verifies the identity claims, then signs the CSR with its own private key, producing a signed certificate (typically a `.crt` or `.pem` file).

4. Install the certificate. The signed certificate and, if needed, any intermediate CA certificates are installed on the web server alongside the private key.

5. Verify the chain. A client browser traces the certificate's issuer back to a trusted root CA. Every link in that chain must be valid.

Key Certificate Fields

When you inspect a certificate in a browser, you will see these important fields:

Trust Chains and Why They Matter

A trust chain (certificate chain) runs from the server's end-entity certificate up through one or more intermediate CAs to a root CA. Browsers trust the root CA and therefore trust anything it has signed — directly or indirectly. If any certificate in the chain is missing, expired, or signed by an untrusted CA, the browser displays a warning and blocks or alerts the user.

A self-signed certificate is signed by the same entity that issued it rather than by a recognized CA. Self-signed certificates are acceptable in closed lab environments, but a real user encountering one in a browser should treat it with suspicion: there is no independent verification of the server's identity.

An expired certificate means the current date is past the Not After date. This is a configuration failure, not an attack on its own, but it signals that the operator may not be maintaining security controls. A real user should not proceed; instead, they should report the issue to the website owner or their IT department and avoid submitting sensitive data.

Using OpenSSL for PKI Tasks

OpenSSL is the standard command-line tool for PKI operations on Linux. Common commands you will use in this lab:

Lab Safety and Best Practices

This lab uses isolated virtual machines. Keep all generated private keys inside the lab environment — do not export them to personal devices or public repositories. Treat private keys like passwords: anyone who possesses a private key can impersonate that server. Use strong passphrases on any key you protect with one. Delete lab CA keys and certificates at the end of the exercise so they cannot be misused outside the controlled environment. Work only on systems you are authorized to configure; never apply lab CA configurations to production or shared infrastructure.

Key terms9

Certificate Authority (CA)A trusted entity that verifies identity claims and digitally signs certificates, allowing clients to trust the identity of certificate holders.
Certificate Signing Request (CSR)A file generated by the entity seeking a certificate; it contains the public key and identifying information and is submitted to a CA for signing.
Trust Chain (Certificate Chain)The ordered sequence of certificates from an end-entity certificate through one or more intermediate CAs up to a trusted root CA.
Self-Signed CertificateA certificate signed by the same key pair it describes rather than by an independent CA; it provides encryption but no third-party identity verification.
Subject Alternative Name (SAN)A certificate extension listing the hostnames and IP addresses the certificate is valid for; required by modern browsers for server authentication.
Key Usage / Extended Key Usage (EKU)Certificate extensions that define the permitted purposes of a certificate's key, such as server authentication, client authentication, or code signing.
Validity PeriodThe date range defined by the Not Before and Not After fields within which a certificate is considered valid.
OpenSSLAn open-source command-line toolkit widely used on Linux to generate keys, create CSRs, sign certificates, and test TLS connections.
Root CAThe top-level certificate authority whose self-signed certificate is pre-installed in browsers and operating systems as an unconditional trust anchor.
In class: Use OpenSSL on a Linux VM to generate a private key and CSR, then submit the CSR to the lab CA and install the signed certificate on an Apache or Nginx test server. · Connect to the test server with a browser, inspect the certificate details, and document the certificate fields including subject, issuer, validity period, and key usage extensions. · Deliberately introduce an expired or self-signed certificate on a second test server, observe browser warnings, and write a one-page explanation of what a real user should do and why.
Materials: Linux VMs with OpenSSL installed, lab CA (e.g., easy-rsa or a simple internal CA configured by instructor), Apache or Nginx web server packages, browser for inspection, lab guide.
Check: Certificate is correctly issued and trusted by the lab browser with no errors; lab report includes correct interpretation of all certificate fields; expired-certificate scenario is correctly explained; score 75% or higher.

Practice check8

Answer each question, then check it. Nothing is recorded; this is your own practice.

CompTIA Security+: Cryptography and PKI
1. During the lab, you run `openssl req -new -key server.key -out server.csr`. What is the primary purpose of this command?
CompTIA Security+: Cryptography and PKI
2. A browser traces a server's certificate back to an intermediate CA but cannot find a valid path to a trusted root CA. What will the browser most likely do?
CompTIA CySA+: Security Operations
3. You inspect a test server's certificate and notice the Not After date is three days in the past. Which certificate field tells you the certificate is expired?
ISC2 CC: Network Security
4. A user visits a site and receives a browser warning stating the certificate is self-signed. What is the most accurate explanation of why this warning appears?
CompTIA Security+: Cryptography and PKI
5. Which certificate extension lists all the hostnames and IP addresses for which a certificate is valid, and is required by modern browsers?
CompTIA CySA+: Security Operations
6. After installing the signed certificate on your Apache test server, you want to verify the certificate's fields without opening a browser. Which OpenSSL command is most appropriate?
ISC2 CC: Access Controls Concepts
7. In the expired-certificate scenario of this lab, what is the safest advice to give a real user who encounters the browser warning?
CompTIA CySA+: Identity and Access Management
8. An analyst reviewing a certificate sees Extended Key Usage (EKU) set to 'Client Authentication' only. This certificate is then presented by a web server for HTTPS. What is the likely result?
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