The send Notification checkbox only related to the fact that the change of the Label(s) should trigger the normal notification flow of JIRA. Same flow as when you would edit other fields of the issue.
So this notification is specific to the issue that's being labeled.
If you want to get a notification for every issue that receives a particular label, you'll have to create filter like this:
labels = "<label>"
When you have saved the filter you can click on Details and create Subscription. More details here: https://confluence.atlassian.com/display/JIRA/Receiving+Search+Results+via+Email#ReceivingSearchResultsviaEmail-SubscribingtoaFilter
Hope this helps.
Usually Notifications are sent in the next minute. If you are having delays of an hour or so in some emails, and since you are on OnDemand, feel free to create a request in support.atlassian.comand we'll search the logs for any errors delivering your mails.
Sometimes Mail servers reject connections or consider some mails spam.
I don't quite understand what "Send Notification checkbox" you are refering to. Is it when performing a bulk operation on several issues?
I hope that answers :)
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