If you do not have JIRA admin rights have the JIRA System Administrator mail cache/queue to see if they are stuck in a backlog.
If the mail queue is empty:
-- then for Confluence the person updating the confluence page removed the notification to Watchers checkbox.
--for JIRA check the system automation rules and see if audit logs reveal anything
So, if the mails leave Confluence correctly but missing in Outlook this suggests there is a spam filter or filtering rules "hiding" the mails - or the mail servers involved (between Confluence infrastructure and your receiving mail server is causing trouble).
Do you have a mail administrator (the one who provides you the mail service) which could help in further debug?
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