If you frequently send Mail messages to specific groups of people, it makes sense to get familiar with setting up and using a Mail group, as it saves a little time and is easy to control.
Appleholic reader Charlie Reich wrote me to lament that the ability to choose a “To” address directly from within the Mail shortcuts bar disappeared with the release of Yosemite.
Charlie used this feature quite extensively when sending mail to groups of friends and family; he found it easier to use the tool to drop an address into the relevant field than it was to begin typing their address. While he can select multiple addresses by depressing the Command key while choosing them, he began using Contacts groups instead.
To set up a Contact group
Launch your Contacts App.
In the window that appears, you should see three panes – information about specific contacts sits to the right, individual contacts are listed in the center and the different contacts sources are listed to the left, thusly: All Contacts, iCloud/All iCloud, All on My Mac.
To create a contact group hover your cursor above the words iCloud and then click the “+” icon that appears (or choose File>New Group
A new listing will appear to the left; by default, this will say "Untitled group." Change it to something relevant, such as “Colleagues," or “People I know who are going to buy an Apple Watch." (Send the latter group this link: “An Apple Watch user guide.")
Now, you must find and select the contacts you wish to include in this collection from your “All” iCloud or Mac contact books and drag-and-drop them to your new Colleagues collection.
All the chosen connections will now appear inside the new contact book.
Smart Contact groups
You can also create Smart groups. Like Smart Folders, these will automatically be populated with contacts who fit parameters you set.
To create a Smart Group select File>New Smart Group in Contacts.
You will be asked to set parameters for the group, by default you will be given a “Card” “Contains” set up. Using this, you could create a group comprising everyone who shares the same domain, or whose contact information says they work at the same company, or anyone called “John” – whatever you like.
Criteria include: Name, Company, Phone, Birthday, IM and conditionals include contain, does not contain and more. Read OS X: Everything you need to use Smart Folders for an idea of how to apply these choices.
You can choose to apply multiple criteria to these groups – just click the “+” button to add another set, or the “-“ button to remove them.
You can use this feature to automatically create and update contact lists, based on information you hold in their Contacts file.
Using Contact groups
These groups are incredibly easy to use. When you are addressing an email all you need to do is type the name of the contact group in the “Bcc” window and hit return to see all the emails of people you’ve selected for that group appear in that window, ready to mail out.
That means that if you have created a group called “Colleagues” all you need do is type that word in the “Bcc” window, hit return and the mail will be ready to send to everyone in that group -- you will not need to enter each email individually.
Such groups are really useful if you need to keep in touch regularly with groups of family and friends.
NB: The reason to leave the “To” window blank and use contact groups to populate the Bcc window is ever so simple: It means people responding to your email will respond only to you, and not to everyone on the list.
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