Issue Summary

When Jira serializes issue payloads for webhooks, the request cache is closed before the comment serialization phase begins. As a result, comment serialization does not benefit from caching, and each comment’s permission check is performed individually against the database. This can lead to significant performance degradation, especially in environments with complex permission schemes (such as nested group relationships).

While the lack of caching is not always problematic for the comments themselves, the repeated permission checks can be extremely slow in certain configurations, causing delays in webhook payload generation and increased database load.

Steps to Reproduce

1. Configure Jira with complex permission schemes (e.g., nested groups, large user directories).
2. Create an issue and add a large number of comments.
3. Trigger a webhook event for the issue (e.g., issue updated, comment added).
4. Observe the time taken to generate and deliver the webhook payload, and monitor database activity related to permission checks.

Expected Results

Webhook payloads are generated efficiently, with permission checks for comments utilizing caching to minimize redundant database queries.

Actual Results

Webhook payload generation is slow. Profiling shows that permission checks for each comment are performed without caching, resulting in repeated and expensive database queries.

Workaround

Currently there is no known workaround for this behavior. A workaround will be added here when available