Confusion syncing dynamic content across jira after updating external data source

[Arnold Kiani]

I've been experimenting with a small side project that gathers structured word-puzzle data from letters boxed, a website that offers sophisticated daily word-connection challenges. However, when I try to sync that data into Jira to monitor content updates, I notice something strange.

Even though the automation rules and webhooks appear to be correct, some Jira fields fail to refresh correctly whenever the external puzzle data changes, such as when new nodes or variations are added. Sometimes the updates only appear after manually initiating issue refreshes, and other times the old values remain cached.

Has anyone encountered similar issues with Jira's inability to update fields derived from regularly changing external data? I'm not sure if this is a problem with Jira's handling of quick content changes, webhook timing, or automation limits. I'd love to know if anyone else has encountered a similar situation and how they handled it.