In some Jira tickets, I have been the Issue Watcher but I don't receive email when the reporter comment. Another user also experiencing a similar issue, sometimes receive and sometimes not. This is randomly happened. Notification Helper Page indicates that our users should be notified, in fact we are not receiving our notifications in JIRA.
Now the Jira server is 8.5.5, is it a bug? does any workaround?
from your description I understand that Notification Helper is stating everything is configured fine - this is good. A first step into diagnosis it perfect to be done by Notification Helper.
The next steps, in case you control the mail server (the one where Jira sends it mails through), would be to check the server logs of the mail server. If you do not have access to it you would need to ask your IT department for help.
Please note that several parts of the mail system could be need to be inspected, depending on your infrastructure.
This means, if there are server based rules for mail sorting or a spam filter - all those pieces also would need inspection by a system administrator.
In the easiest of all cases a client based spam filter is in place. But this is such a obvious thing so it sometimes is just not mentioned.
Note: for outgoing mail debugging on Jira Server there is also the possibility to extend logging on Jira's Server side:
Please accept my apologies for not making it anymore specific - the root cause needs to be found in your infrastructure. However, Community members have no access to it, advice must come from your IT department, hoping you have one in place.
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