Digital Ocean PAT Expiration On Jenkins Infra: 2025

Heads up, Jenkins enthusiasts! The Digital Ocean PATs (Personal Access Tokens) utilized by Terraform for infra.ci.jenkins.io are set to expire on October 30, 2025. This article outlines the steps required to ensure a smooth transition and prevent any disruptions to the Jenkins infrastructure. Let's dive into the details and make sure everything is up-to-date!

Understanding the Importance of Digital Ocean PATs

Digital Ocean Personal Access Tokens (PATs) are crucial for the Jenkins infrastructure as they enable secure communication and automation between Jenkins and Digital Ocean services. These tokens act as credentials, granting Terraform the necessary permissions to manage and provision resources within the Digital Ocean environment. Imagine them as the keys to the kingdom, allowing Jenkins to seamlessly interact with its cloud infrastructure. Without valid PATs, automated tasks like spinning up new servers, configuring networks, and deploying applications would grind to a halt. Therefore, ensuring the timely renewal and proper handling of these tokens is paramount for maintaining the stability and reliability of the Jenkins CI/CD pipeline. In essence, PATs are the backbone of the infrastructure automation, and their expiration could lead to significant disruptions if not addressed proactively. Think of it as changing the locks on your house – if you don't distribute the new keys, no one can get in! Similarly, outdated PATs can lock Jenkins out of its own infrastructure, highlighting the critical need for vigilance and timely action.

The previous token rotation, documented in https://github.com/jenkins-infra/helpdesk/issues/4740, serves as a valuable reference point for this upcoming expiration. By reviewing the steps taken during the previous rotation, we can gain insights into best practices and potential challenges, ensuring a smoother and more efficient process this time around. It's like learning from past experiences – we can identify what worked well and what could be improved, ultimately minimizing the risk of errors or delays. This proactive approach to token management demonstrates a commitment to maintaining a secure and reliable infrastructure, safeguarding the Jenkins ecosystem from potential disruptions. Moreover, documenting these procedures ensures that the knowledge is shared and readily accessible to the team, fostering collaboration and preventing single points of failure. In short, learning from the past is crucial for a successful future.

Step-by-Step Guide to Renewing Digital Ocean PATs

To ensure uninterrupted service, follow these steps to generate new tokens and update the infrastructure:

1. Generate a New Pair of Tokens

The first step in this critical process involves generating a fresh pair of Digital Ocean PATs. This requires logging into DigitalOcean as the designated "Jenkins Infrastructure Technical User," which is associated with the email address jenkins-infra-team@googlegroups.com. This account is specifically set up for managing infrastructure-related tasks, ensuring a clear separation of concerns and enhanced security. Once logged in, you'll need to utilize the Time-based One-time Password (TOTP) for two-factor authentication (2FA). The runbooks available at https://github.com/jenkins-infra/runbooks/blob/main/shared-totp/README.adoc provide detailed instructions on how to use the shared TOTP securely. This added layer of authentication is crucial for protecting sensitive credentials and preventing unauthorized access to the infrastructure. Think of it as a double-lock system, ensuring that only authorized personnel can make changes to the system. By following these security protocols diligently, we can maintain the integrity of the Jenkins infrastructure and safeguard it from potential threats.

Next, navigate to the "API" section, then "Applications & API," and finally the "Tokens/Keys" tab within the Digital Ocean interface. Here, you'll find the existing tokens that need to be regenerated. It's important to note that these tokens should be treated with the utmost care, as they grant access to critical infrastructure resources. If the existing tokens have disappeared (which can sometimes happen due to various reasons), you'll need to create new ones. When regenerating or creating tokens, set a Time-to-Live (TTL) of 90 days. This shorter lifespan enhances security by limiting the window of opportunity for misuse in case of a compromise. For the infra.ci-production token, grant both Read and Write permissions, as this token is used for managing production resources. The infra.ci-staging token, on the other hand, should be assigned Read-Only permissions, aligning with the principle of least privilege and minimizing the potential impact of any accidental or malicious modifications. This careful assignment of permissions is a fundamental aspect of secure infrastructure management.

2. Update Tokens in the Infrastructure as Code (IaC) Setup

With the new tokens generated, the next crucial step is to update them within the Infrastructure as Code (IaC) setup. This ensures that the automated processes managed by Terraform utilize the new credentials, maintaining the integrity and functionality of the Jenkins infrastructure. The first place to update the tokens is within the SOPS (Secrets Operations) encrypted secrets, located in the jenkins-infra/charts-secrets repository on GitHub. SOPS is a powerful tool that allows for the secure storage and management of sensitive information within Git repositories. By encrypting the secrets, we protect them from unauthorized access while still enabling them to be managed alongside the infrastructure code. Updating the SOPS encrypted secrets involves decrypting the existing secrets, replacing the old tokens with the newly generated ones, and then re-encrypting the file. This process ensures that the tokens are stored securely and can be accessed only by authorized processes.

Once the SOPS encrypted secrets are updated, the next step is to trigger a build of the jenkins-infra/kubernetes-management repository on its main branch. This repository contains the configuration and deployment scripts for the Kubernetes infrastructure that supports Jenkins. By running a build, we ensure that the updated secrets are deployed to the Kubernetes cluster, making them available to the services and applications that need them. This process typically involves using a CI/CD pipeline, such as Jenkins itself, to automate the deployment process. The pipeline will retrieve the updated secrets from the SOPS encrypted store, inject them into the Kubernetes configuration, and then apply the changes to the cluster. This automated deployment process ensures consistency and reduces the risk of human error.

After deploying the new secrets, it's essential to reload the Jenkins Configuration as Code (JCasc) on infra.ci. JCasc allows for the management of Jenkins configuration through code, ensuring consistency and reproducibility across different environments. Reloading JCasc ensures that Jenkins picks up the new credentials from the updated secrets and applies them to its configuration. This process typically involves sending a signal to the Jenkins instance to reload its configuration from the JCasc file. By reloading JCasc, we ensure that Jenkins is using the latest credentials for its interactions with Digital Ocean, preventing any authentication issues.

3. Verify the Jenkins Infrastructure

After updating the tokens, it's essential to verify that the jenkins-infra/digitalocean job is back to a successful state. This job is responsible for managing the Digital Ocean infrastructure using Terraform. To verify, trigger a new pull request (PR) or a main build of the job. A successful run of this job confirms that Terraform can authenticate with Digital Ocean using the new tokens and that the infrastructure is functioning as expected. Monitoring the build logs and output is crucial to identify any potential errors or warnings. If the job fails, it indicates an issue with the token update process or the Terraform configuration. In such cases, it's necessary to investigate the logs, identify the root cause, and take corrective actions. This verification step is critical for ensuring the overall stability and reliability of the Jenkins infrastructure.

4. Schedule a Reminder for Future Token Rotation

To prevent future expirations from causing disruptions, it's crucial to add a calendar event as a reminder. Set the event for 90 days from the token generation date, with a 2-week alert. This proactive approach ensures that the token rotation process is initiated well in advance of the actual expiration date, providing ample time to address any potential issues. The calendar event should include all the necessary information, such as the token expiration date, the steps required for token renewal, and the relevant contact persons. This reminder system acts as a safety net, ensuring that the token rotation process doesn't slip through the cracks. By incorporating this practice into the workflow, the Jenkins infrastructure team can maintain a proactive stance on security and avoid potential service interruptions.

Conclusion

Renewing Digital Ocean PATs is a critical task for maintaining the health and stability of the Jenkins infrastructure. By following these steps diligently, you can ensure a smooth transition and prevent any disruptions to your CI/CD pipeline. Remember, proactive maintenance is key to a robust and reliable system. Don't wait until the last minute – schedule your token rotation today!

For more information on Jenkins infrastructure management and best practices, be sure to check out the official Jenkins documentation and community resources. You can also find helpful guides and tutorials on websites like Jenkins.io. Stay informed, stay secure, and keep your Jenkins environment running smoothly!