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If you can find any error logs near the times time when the repeatings occurred executed successfully last time, please create new support ticket with details. The logs are written to the log subdirectory of your Jira application home directory (or elsewhere if you have configured a different location). File: atlassian-jira.log.

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  1. Sometimes there are some problems with cached index for Jira search service during the app update process. This may cause that the repeated issues are not scheduled properly after app update (because issues are not found). Finally, the repeated issues may have properly calculated next occurrence date but their status will be INTERRUPTED. This happen in nondeterministic way and we did changes in the app version from 3.1.0 to try prevent such situations.
  2. When the app is temporary uninstalled, all issues to which any change are made will be indexed without data of repeated issues. After subsequent app installation such situations can either lead to repeatings with INTERRUPTED status, or repeatings may be not visible at all.
  3. The Repeating Issues App versions from 0.15.1 up to 3.6.0 may interrupt repeatings when UPM will run self update process or other apps are uninstalled.

Solution
Go to app administration page (Jira Administration > Issues > Repeated Issues) and check if you can find any repeatings with INTERRUPTED status. If present, reset all repeatings using "more" menu (...) on app administration page. If you suspect there are some missing repeatings, please reindex the Jira and after finish, reset all repeatings on app administration page.

From version 3.5.0 the app has feature to check and report for interrupted repeatings. It is a scheduled job that runs every night and is searching for interrupted entries. When any exist the the email notification is sent to Jira administrators. These checks also try to re-schedule again such repeatings automatically. The job also print the check result in Jira logs with INFO logging level. Please read following How to get more logs from the Repeating Issues app?.

Codedoers suggest you to have always the the latest Repeating Issues app version.