This article demonstrates how to configure a webhook that automatically converts failed automated tasks into trackable Jira incidents to ensure your systems remain reliable and compliant. By following this guide, you will eliminate silent automation failures and gain real-time visibility into operational issues before they impact your organization.
We provide a comprehensive technical walkthrough to bridge the gap between background task execution and active incident management within your Atlassian ecosystem.
In our video, we walk you through the entire configuration process for setting up these automated alerts from start to finish.
https://youtu.be/aLO-Yr50EZU?si=qw9UCDUMNAVk1PdF
The Critical Importance of Trustworthy Automation
Automations are designed to save time and reduce manual overhead, but they are only truly effective if they are trustworthy. In many enterprise environments, administrators rely on “set-and-forget” tasks to handle vital processes such as user offboarding, governance routines, and license management. However, when these tasks quietly stop working, the consequences can be severe. You might find that license spend is creeping up because accounts aren’t being deactivated, or sensitive data remains accessible because an offboarding routine failed. If no one is manually checking the logs, these failures can go unnoticed for weeks, creating significant compliance risks and operational debt.
In our video, we emphasize that manual checking simply does not scale in a large organization. When you are managing hundreds or thousands of users, you cannot afford to wait for a manual audit to discover a problem. Instead, we must treat every task failure as a formal operational event. This means the system must be capable of detecting the failure, routing the information to the correct team, and tracking the resolution through a standardized workflow. Our goal is to ensure that you find out about a failure before your boss does, maintaining the integrity of your IT infrastructure.
Step 1: Configuring Jira Automation for Incoming Signals
The first step in building this failure notification system is to set up a Jira automation rule that can receive signals from external applications. You will need to navigate to your space settings and find the automation section. While you can build these rules at various levels, we recommend focusing on your IT Ops or Jira Service Management (JSM) project to ensure the right eyes are on the resulting tickets. To begin, create a new rule from scratch and select the “Incoming Webhook” as your trigger.
Setting the Trigger and Action
When you configure the incoming webhook trigger, Jira will eventually provide you with a unique URL and a secret key. However, these details are often only visible after the rule is saved and turned on. The next part of the process is defining the automation action. In our example, we choose to “Create a new work item.” For most organizations, setting the issue type to Problem or Incident is the best approach for tracking automation failures. This allows the failure to be prioritized alongside other technical issues in your queue.
Customizing the Work Item Details
It is essential to populate the work item criteria with useful information. For the summary, we suggest something clear like “Automated task failed.” In the description field, you should include actionable instructions or notes on where the administrator can find more specific details about the failure. One vital technical setting to remember is changing the work item criteria to “No work items from the webhook.” This ensures that the rule runs successfully without requiring an existing issue context, which is necessary since the failure is generating a brand-new ticket. Once these settings are finalized, turn on the rule to generate the necessary Webhook URL and Secret.
Step 2: Connecting the User Management App
With the Jira side of the integration ready, the next phase happens within our user management app. This app serves as the source of the automation tasks and is responsible for sending the “signal” when something goes wrong. Navigate to the settings menu and locate the section for Atlassian Automation Webhooks. This is where the bridge between the app and Jira is built. You can find the app on the Atlassian Marketplace if you haven’t installed it yet.
Registering the New Webhook
Click to create a new webhook and give it a highly descriptive name, such as “Automated Task Failed to Jira Problem.” A clear naming convention is critical for long-term governance and clarity, especially when multiple admins are managing the system. You will then need to paste the Webhook URL and the Secret that you generated in the previous step in Jira. It is important to treat this secret like a credential; do not share it or paste it into insecure locations, as it authorizes the communication between the two systems.
Selecting the Correct Trigger Event
The user management app supports several triggers, but for this specific workflow, you must select “Task Failure.” This ensures that the webhook only fires when an automated execution fails to complete. You also have the option to add notes to the webhook configuration, which we highly recommend for documentation purposes. Once you have toggled the webhook to “Active” and saved your changes, the link is established. For more technical details on this process, you can read the documentation provided by our team.
Step 3: Testing and Operational Verification
Configuration is only half the battle; verification is what guarantees the system will work when a real crisis occurs. Within the user management app settings, there is a run test feature specifically for the task failure trigger. When you click this, the app sends a test payload to the Jira URL you provided. You should receive immediate feedback from the app indicating whether the signal was sent successfully, but you must also verify the results within Jira itself.
Reviewing the Audit Log
The Audit Log in Jira Automation is your best friend when troubleshooting or confirming new rules. Check the log to see the event entry created by the webhook. The log will show you exactly what happened when the signal was received and should confirm that a new issue was created. If there are any errors in the field mapping or permissions, the audit log will highlight them here. This is a crucial step in ensuring that your IT operations are running as expected.
Confirming Ticket Creation
Finally, navigate to your issue queue or board. You should see a brand-new ticket titled “Automated task failed.” This confirms that the entire automation loop is closed. Now, instead of a task failing silently in the background, it is a trackable work item that can be assigned to a team member, prioritized, and fixed. By following these steps, you move from a reactive state to a proactive operational model, ensuring your automations remain a reliable asset rather than a hidden liability.
Best Practices for Ongoing Management
Once your webhook notifications are live, there are a few operational tips to keep in mind. Always revisit the automation audit log after making changes to your tasks or Jira workflows to ensure nothing has broken the connection. Furthermore, consider rooting different types of failures to different teams. While we showed a simple “create issue” action, Jira Automation is flexible enough to send real-time notifications to Slack, Microsoft Teams, or email simultaneously. This ensures the right team gets the alert in the platform they use most frequently, further reducing the mean time to resolution for automation failures.
