I went in to "Tools-Email Accounts and then under directory I went to
veiw or change existing directories or address books, Removed the old
entry because it pointed to the old server and then added a new address
book. This automaticly brought the sub folder contacts with it which
showed no entries. I then right clicked on my contacts folder in the
folder view went ot properties - outlook address book and unchecked
Show as outlook address book. I then shutdown and restarted outlook
and then re added my contacts folder as an address book but still no
entries under the contacts subfolder of outlook address book when I
click on "To" when trying to send an email. If I go in to contacts in
the folder view i see 500 entries with email addresses.

If I open a contact, highlight the email address do a "ctrl x" to cut
and then do a "ctrl c" to copy it back then click on "save and close"
this contact will show up under the contacts subfolder when I click
"To" in a new mail message.

Does this help you out more