Hello @Francesco Santi
Your requirement of sending mail notification on workflow transitions is easily supported out of the box by Jira. So when your task arrives at the status "deadline date" then you can configure an event like "Issue Update" on the workflow transition and in the notification scheme configure to send an email on this event to all involved stakeholders.
Yes..use filter subscription.
For more information please visit the below article.
https://confluence.atlassian.com/jira064/receiving-search-results-via-email-720416706.html
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Yes, you can send the email automatically, after coming the new update of gmail it is now even easier, you can visit gmail customer care to know the steps to do the setup for sending email automatically.
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