Q: How can I send an email to all of the email addresses associated with one contact? Similarly, in regard to group lists, how do you include for distribution all email addresses associated with each contact in the group?

I don't believe there is an easy way. The only thing I can think of would be to create multiple groups and set different email addresses in each. I haven't tried it, though.

Don't be surprised.

Apple offers free, basic Mail and Address Book apps and creates paid, more sophisticated solutions, also allowing Developers to provide more sophisticated solutions for sale in the marketplace.

When I need to repeatedly email to multiple contacts, I create a blank draft email, and use the Address Book button to list the appropriate address book group. With the Address Book window open, it's easy to click to add multiple email addresses for a single contact name. Each is added to the message email address list. Then I save that blank email to iCloud Drafts, and it retains the email addreses I've entered. Next time I need to send a message I double-click on it in Drafts to open it, and drag it to one of my other email accounts to add Subject and details, then send from the other account.

Message was edited by: kostby

Another way to manage that list is to create a text clipping of the addresses. Address an email with all the addresses you need, select them all, then drag the whole list to the Desktop (or another location). That will create a text clipping. You can drag that text clipping back into the To field of a new message.

That allows you to keep the addresses out of your Contacts if their only purpose is to contact the team.

There is an easy way that is built in. Open AddressBook, highlight the group's name, on the menu, click, "Edit," then select, "Edit Distribution List." Then highlight the individual address to be used by that group.

From that point on, when you enter the name of the group into one of Mail's address fields, it will go to the addresses that you selected.

Sorry, misread your question.

I had to make a duplicate of the contact in Contacts, with the second email address. Then I created a group with both contacts and I email to that group. It's a clumsy solution but it's the only way I can automatically email to both email address someone has.

I found this reply to this problem in another discussion group (not Mac).

In your contacts, select the mail list/group. You should see each "contact". Then select the contact with multiple emails. This will take you to the details for that individual contact. Near the top, under the area where it says "job description, Company" you should see a little drop down with the name of the list/group in it. Click the down arrow, which will expose the multiple addresses. Next to each email, there is a check box. The ones checked will get mail when sent to the list, so put a check in the additional email address checkboxes. Once you do this, moving forward, all mails to the group will get the email, including the multiple addresses you checked.

But I cannot find the pull down menu mentioned. What am I missing here?

Thanks for this most helpful tactic.  I am using it to individually address to multiple contacts an email with some customised content but a large body of common content.  It will save me a lot of hassle.

My Apple ID address won't eliminate from a smart list when I don't want it.  Two addresses are listed for me in the Smart List Edit Distribution List Box, and I cannot figure out how to eliminate one of them .  The correct address is selected in the first listing, but the second listing (My apple id address) springs back after I click the correct address and close the dialog box.  I tried adding a company and job title listing (even though I'm not one) but no check box re selecting which address.  Running new MacBook Pro and El Capitan up to date.