Information Technology Reference
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dressing more accurate. To do this, choose Window > Previous Recipients, and
then select and delete any addresses you don't need. (Try sorting the addresses
by Last Used to easily find ones you haven't used in a long time.)
Tip: If a contact has more than one email address, you may find it helpful to create a
separate Contacts entry, with a different name, for each alternative email address. To
learn more about why and how you might do this, read Jeff Carlson's TidBITS article
Prevent Apple Mail from Auto-Completing the Wrong Address .
Multiple addresses: If you type or paste an email address into an address field
(as opposed to using autocomplete for an address Mail already knows) and want
to type another, press Return or type a comma. Mail then encapsulates the ad-
dress you've just typed in a tidy blue bubble, and is ready for the next one.
Groups and smart groups: The Contacts app lets you create groups of ad-
dresses—for example, a Family group that contains the contact records of your
family members. You can type a portion of a group's name and Mail autocom-
pletes it just as it would for an individual name. Autocomplete does not work for
smart groups you created in Contacts, but if you type the entire, exact name of
the smart group, then even though Mail doesn't autocomplete it, it does appear
in a nice blue bubble after you type a comma or press Tab or Return, and the
smart group does work—Mail sends the message to the correct addresses. The
failure to autocomplete smart addresses is most likely a bug, and I expect the
problem to be fixed at some point.
Group Address Options
When you address a message to a group, Mail can either expand the group name into
the individual addresses (the default setting) or simply leave the group name as the
only addressee. To toggle this setting, go to Mail > Preferences > Composing and se-
lect or deselect When Sending to a Group, Show All Member Addresses.
Prior to Mavericks, if this checkbox was deselected, recipients of the message wouldn't
be able to see each other's addresses, even if the group address was in the To or Cc
field rather than in Bcc. However, in Mavericks (including 10.9.2), even though Mail
doesn't show you the individual addresses, the recipients do see them. I don't know if
this is an intentional design change or a bug, but in any case, if you want to be sure
group recipients don't see everyone else's address, you must put the group name in
the Bcc field.
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