I'm using a Jira 5.2.11 webhook that fires based on a simple JQL query to update data in another commerical tool through its REST API. That JQL query is
project = Test_Belair and "External IDs" is not empty
It works fine except in one case, when the Jira issue is transitioned from Resolved status back to Open status (i.e. it failed). I've played around with my workflow post-functions and even added a post function to explicitly call the webhook but the webhook is never called. I know this because the first thing I do is call a simple logging routine to write a message to a local file. It worked in all the other scenarios that I'm testing.
When I read the "Known Issues" for Managing Webhooks in 5.2, the only issue that comes close is
Post function web hooks will not fire if added to the Create Issue workflow transition. We recommend that you configure your web hook to fire from the issue_created event instead.
If anyone has some ideas/suggestions that would be great. Most of the existing questions around webhooks don't seem to be answered.