Verify the Webhooks setup in your instance of Jira Software [Cloud, Server] can reach the internet. Can the Jira WebHooks connect to the outside world?
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Jira Software Data Center ONLY: Verify that a HTTP/S request sent from your on-premise Jira Software instance to our piplanning.io servers/listeners succeeds.

Verify in your Jira instance that the Jira WebHook Add-on/Apps (modules) are activated, and 2nd that the WebHooks are being triggered.

Go to the website: https://webhook.site

Find the Your unique URL field. We will copy the value from this field.

Copy (click Copy) on the Your unique URL field.

Important: Please copy the Your unique URL value using the Copy link, do NOT copy from the URL address bar!)

​Note: Keep this browser tab open for this webhook.site page because we will refer to it later to get the test result.

Navigate to Jira > System > WebHook.

Create a NEW WebHook in Jira using that value from the (webhook.site) Your unique URL field. This new Jira WebHook is for testing purposes only and you can delete it after the test is validated.

Note: create this new Jira WebHook with the same Issue related events and Jira Software related events (Sprints, Boards) as described in our documentation for Add Jira WebHook (link TBP).

Return to the Jira UI, please Create or Update an Issue in Jira to trigger the Jira WebHook.

Note: Changing a field in Jira is supposed to trigger the event that fires a WebHook.

Navigate back to the https://webhook.site page, and observe if you see any WebHook requests.

Question: Is there a Jira WebHook received by https://webhook.site? 🤓

Go to the RTE Cockpit > ALM Connections > Jira - Webhook page.

Copy the URL on the Jira - WebHook setup page directly into a browser tab

Important: Perform some actions in Jira to trigger the WebHook events. Actions such as: move User Stories into a Sprint, edit the Name of a User Story. Create/Update User Stories or any Jira Issues that is in the Jira WebHook scope (JQL).

Return to the browser tab and validate that the entries in the JSON response and the last_request_timestamp array.

Open a Terminal window on the Jira Software host machine to access the Shell.

In the Shell program (Linux) from the command line issue the following command:

curl -v -d "test=1" -X POST https://wlistener2.piplanning.io/foo:jira:bar

IF the request fails (Timeout, DNS error. etc.), then it is most likely a network issue (e.g. Firewall). Please investigate with the appropriate network team and resolve this.

Download the two letsencrypt root certs:

Add it to the Jira trust store following the official Atlassian docs: https://confluence.atlassian.com/kb/how-to-import-a-public-ssl-certificate-into-a-jvm-867025849.html

Choose step 1 a). or 1 b). depending on the Jira Software instance you have:

Enter com.atlassian.webhooks for the Package name → Set Logging Level to DEBUG → Add

Note: For more verbose logging, enter org.apache.http for the Package name → Set Logging Level to DEBUG → Add

Mark the logs as per Marking Jira logs for troubleshooting purposes to indicate Replication Start

Trigger the WebHooks (a single event should be able to trigger both WebHooks)

Note: This will only log an entry when the WebHook has been triggered, so if you don't see any entries, the WebHook is not triggering.

Go to Settings > Jira Settings > Apps

Click Manage apps menu in the left menu navigation.

In the first filter box in the right pane, the default text reads Filter visible apps, , enter WebHook

In the second filter box, select the dropdown and select System

Confirm the two (2x) WebHooks Plugins are installed, refer to the screenshot.