Jira Automation incoming webhook intermittently not triggering (first attempt fails, second succeeds

Question

Hi everyone,

I’m troubleshooting an issue with two Jira Automation rules connected via an incoming webhook.

Setup:

* Outgoing rule: Triggers when a customer adds a comment and sends a POST request to the incoming webhook URL.
* Incoming rule: Uses the incoming webhook trigger, followed by actions to transition the work item and edit its fields.

Issue:

The first attempt does not seem to trigger the incoming rule. The outgoing rule’s audit log shows “Successfully published web request”, but there is no corresponding entry in the incoming rule’s audit log and no error message.

When I try again, the incoming rule works as expected.

What I’ve checked so far:

* The webhook URL matches the one configured in the incoming rule.
* The outgoing rule reports that the web request was published successfully.
* The incoming rule sometimes works on a subsequent attempt without any apparent configuration changes.

Has anyone encountered a similar issue where the first webhook request does not trigger the incoming rule, but a subsequent request does?

What else should I check to determine whether the issue is related to webhook delivery, authentication, or the incoming trigger itself?

Thanks in advance!

Integration Yard · Answer

Adding to the AUTO-2286 workaround: since both rules live in the same Jira site, you may not need the incoming-webhook hop at all. Two options that skip it: (1) do the transition/edit directly in the first rule (Automation can branch on the related work item and act on it); or (2) have the second rule use a normal trigger (e.g. "Work item transitioned" or "Field value changed") and turn on Rule details > "Allow rule trigger" so actions from the first rule can fire it. That's rule chaining, with no HTTP call that can be dropped on a cold start. If you must keep the webhook (e.g. the caller is external), send only the issue key and look the work item up in the second rule. That keeps the payload small and makes a retry from the sender safe.

Arkadiusz Wroblewski · Answer

Hello @Zhiwei

Oops, sorry @Nikola Perisic, by coincidence I posted that in your Bitbucket post 🫣😂👀 Too many tabs open is a Cancer.

There's a related bug:

https://jira.atlassian.com/browse/AUTO-2286

Atlassian recommends adding a 10-second delay before sending the webhook or sending only the issue key.

Your case is slightly different because there's no audit log entry. If the workarounds don't help, please contact Atlassian Support and reference AUTO-2286.

Cheers,

Arek🤠🧙‍♂️

Zhiwei · Answer

Hi @Nikola Perisic,

Both the outgoing and incoming rules are within Jira. The outgoing rule sends a POST request to the incoming webhook trigger of another Jira Automation rule.

The issue is intermittent. Sometimes the incoming rule doesn't trigger for the first few attempts, with no corresponding audit log entries or error messages, but it eventually works after several attempts. For example, it might only work on the fourth attempt.

I'm not sure what is causing this.