We found that checking that box for single valued fields gave an unhelpful error "Eror creating issue: Error occurred while creating issue. This could be due to a plugin being incompatible with this version of Jira. For more detials please consult the logs, and see: http://confluence.atlassian.com/x/3McB"
I assumed that checking the box did not matter because it only applied to multivalued fields. The text could usefully say "Only check for multi-valued fields"
You are right, the description of the checkbox should be more explicit. Checking it for an invalid field type will create an error. Of course, the configuration screen could disable the checkbox based on the field type, but that would be much more complicated to implement.
As for reporting issues, please see https://innovalog.atlassian.net/wiki/display/HOME/Getting+Support.
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