The field I have created for Number of attachments works on new attachments. Did did not find an existing or closed issue that attachments added before adding custom field are not included.
If I restart Jira will that solve the problem?
I would guess that there is a count (+1) for each attachment that you upload. I would be surprised if the issue itself would hold the information on how many attachments are bound to that issue in general. That info is probably just being stored in that custom field (as soon as you start using it) so I doubt that restarting would change anything. Correct me if I'm wrong :-)
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