Novax,

The contact issue you are experiencing is new to me. The information you have provided does suggest an indexing issue with the contacts.

Not sure if this will work, but attempt an export of all contact data from your boss's PC. Export it to a .CSV and see if the data correctly exports. This essentially will make a back up of his full contact list outside of the active directory list.

It is recommend that you import the contacts to a new test account just to validate the data is not corrupted. You can then remove the contacts from his mailbox and import the .CSV. See if this work around fixes your issue.

Hope this helps..