Cindy wrote:

Is there a way to set up the names we want to appear when Outlook
automatically suggests a name in the To field?

Open a compose window, enter in the "To" field the address you want to load
in the autocompletion cache, then press CTRL-K (or click Check Names). When
it underlines, it has been resolved and will then be available in the name
cache. You can close the Compose window without sending the message. If
you want the person's friendly name to be a part of that string, enter it as
well, like

John Smith

and then press CTRL-K. The next time you compose a message, you'll be able
to start typing "John" and it will pop up.

There are times when I type in a name/part of a name in the To field
(that is confirmed in my contacts), but Outlook doesn't spit back a
match. It shows up when I hit 'Check Names', however.

The autocompletion feature does not reference your contacts in any way
whatsoever. All it does is store addresses that have been resolved.
--
Brian Tillman