There doesn't seem to be the same gear icon available as in old Jira?
This is not possible wihout some development/scripting. You will have to write a listener to check if the custom field is changed and then throw a custom event.
Using the script I commented below it's very easy to create a listener. Give it a try. There's a lot of documentation, from experience :D
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Hi Marco, you could try the Script Runner plugin. It has Builtin Script Listeners that you can configure to send a custom mail as notification.
Hope this helps!
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What you could do is create a circular transition called "Set Planned Date" that returns to the same status as where it's called from and assign it a new event (which you can create in "Admin - Advanced - Events").
If you wish to send a custom mail with it's own HTML and different from the typical JIRA email, then I suggest you look into the "Email This Issue Plugin".
Hope this helps,
Jacques.
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