Ok...yes, I believe I have had that problem as well.
Try this...
This method is the one I now use to get contacts from my Mac "Contacts" into my Outlook contacts:
Obtain the free software called "AB2CSV." It has a User Guide and a welcome screen, but the software is not entirely easy to figure out, quite frankly. Anyhow, once opened, close out the welcome screen and a small square execute box appears. First, go
to the top menu screen of your computer and select the "AB2CSV" bold letters and go to the Preferences. Here you can select "entire address book" or you could possibly select a group of addresses that you may have previously set up in your mac contacts, such
as a Smart Group, for example. After setting up your AB2CSV preferences the way you want them, go back to the small execute box and when you click on it now it will ask you where you'd like to store the .vcf cards that it will make. Store those in a folder
on your desktop, perhaps. Now go back to Outlook and open up Contacts in Outlook. Now, simply drag and drop the .vcf cards from the desktop folder into the Outlook Address Book.
This method works every time for me, and is the one I use instead of my above method.
~TD