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How the "Issue Workflow" action work?

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Repeating Issues add-on allows to select one of this three transitions: 'start progress', 'close' or 'reopen' when set-up 'Issue Workflow' repeats. Choosing 'reopen' for 'Issue Workflow' action means the action will be executed successfully at selected date only if the issue will be in CLOSED status. It is not possible to 'reopen' issue if the issue has IN PROGRESS status because there is no such transition in simple workflow. Remember that also any other transition conditions must be satisfied if the 'reopen' transition has them configured in workflow definition.

How to set time when the repeating action is being executed automatically?

Versions >= 0.3.0

Just set the time in "Starts on" field. The repeating issue will execute automaticaly at defined time (from field 'Starts on") and with given recurrence rule.

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There should be more detailed messages what exactly happens and why the recurrence fails. Administrator should find for logs like this:

2016-06-10 17:17:00,045 atlassian-scheduler-quartz1.local_Worker-1 ERROR user@domain.com [jira.issue.clone.IssueCloningService] Could not clone issue TEST-408.
 Error messages:

 Errors:
   1. The reporter specified is not a user.
   2. User 'testUser' does not exist.
 
2016-06-10 17:17:00,045 atlassian-scheduler-quartz1.local_Worker-1 ERROR anonymous [jira.issue.recurrence.RecurringIssueExecutor] CloneIssue action failed for issue TEST-408.
 Error messages:
   1. Could not clone issue because of unexpected error. Please contact with your Jira administrator

If you find problems that you can't solve with Jira proper configuration then create the ticket with logs details at https://codedoers.atlassian.net/projects/SUPPORT