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

    The Repeating Issues add-on does not allow to set exact time when specific action for given issue will be executed. Add-on allow users to define only days when repeating action should be applied. Actions are executed automatically every day at ~00:15 am

  2. How the "Issue Workflow" action work?
    "Issue Workflow" action allows to run any status transition on the issue that can be executed manually from JIRA issue view. It works the same as clicking on available workflow transition: 'Start Progress', 'Close', 'Reopen' or any other transitions defined in the workflow related with the issue.

    It means for example:

    There is simple workflow that allow for below status transitions:
    1. OPEN > IN PROGRESS (transition 'start progress')
    2. IN PROGRESS > CLOSED (transition 'close')
    3. CLOSED > OPEN (transition 'reopen')

    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.