How can I email a list of users from a custom Context Field?

Question

I have created a custom Context Field under Project Settings -> Issue Types. I have used the People type so I can select many users. I want to set up an email automation that can email the users selected, but when I dereference my custom field using smart values ({{customfield_15308}}) (by printing it out in the body of the email), I don't see an email address property there. If I drop it in the To field, I just get the error below

Send email

Could not send email, the 'To' address field is empty. If you have referenced a field it may be empty.Is there a way to send an email to each person in my custom Context Field using automation? Everything I have tried has failed thus far.
Thanks!

drgilby · Answer

Great suggestions. I was going to go with option 3 in your list, but was holding out for a better solution :) .

Thanks again, I have what I need and have upvoted that feature request.

Bill Sheboy · Answer

Until that suggestion/defect with People-type fields is addressed, the options are limited...

* create a saved filter to detect when issues transition to that specific status, tell stakeholders about the filter, and let them subscribe to it at their desired cadence
* add all the interested stakeholders as issue "watchers", and let them add/remove what they want to see via their profile.  It will be a bit noisier than your idea of only notifying on one specific transition, but it is easy.
* add their email addresses explicitly to another field (e.g. text) and parse those for notification in the automation rule
* and the brute force solution: using the values in the people field, let the automation rule repeatedly call the REST API to get their user information and email address, sending an email for each.  This one seems a bad idea, as the rule will be slow and could lead to rule throttling/usage limit issues

drgilby · Answer

Thanks for the response. We do have a Team-managed project and I upvoted that feature request.

Ultimately what I would like to do is be able to specify a list of stakeholders for an issue and use automation to email them when the issue moves to a specific state (i.e. it's ready for a stakeholder to review the item). Maybe there is a built-in field that might work rather than me creating a custom field?

Thanks again for the response.