Transferring contacts from a Mac with Address Book to a Windows PC with Outlook is challenging. If you’re considering this, you may need professional help to make it happen. If you’re adept with both OS X and Windows, this guide might help.
OS X Mac Mail transfers of POP3 email messages to Windows Outlook are discussed in another posting, since on the Mac contacts and email are integrated but completely separate entities. In Windows, the contacts are an integral part of Outlook. Transfers of documents, pictures and music from a Mac to Windows are also problematic and are covered in another posting.
Getting contacts from Mac Address Book to Outlook is tedious because these two programs do not talk well to each other. That is, they don’t use the same export/import conventions. Because of this, contacts transfers may fail or may contain garbled information. That is unacceptable. The final result has to be perfect or the end user will be upset. I do this for other people who pay me for a good result. So a perfect outcome is not only desirable but a necessity.
Method 1 (Fail): When export is chosen in the Mac Address Book, and vcard is chosen as the file format, a single vcard file is created that contains all of the contacts. From the export menu, the user cannot choose one vcard per contact. This works fine when importing to the Address Book on a different Mac, but Outlook can only read the first entry in the vcard file because Outlook only expects one contact per vcard file. Groups were not exported.
Method 2 (Fail): Another way to export contacts from the Mac Address Book involves using automator to create separate vcard files, because by default Mac Address Book export creates a huge vcard file containing all contacts. I tried this and it did create separate vcard entries for each contact. However, Outlook didn’t match the fields properly on import and some fields were missing, including a few important ones like the second line of a primary address. The second line typically contains suite and apartment numbers. Groups were not exported.
Method 3 (Fail): In the Mac Address Book export menu, one can specify a CSV file but in my experience this is a last resort because the field mapping to Outlook is fickle and unpredictable. In fact CSV field mapping even from OE to Outlook is fickle, and they are related products.
In my experience, the only way to transfer contacts (including groups) from Mac to Outlook is to use temporary email clients as go-betweens. These are high quality email clients you weren’t intending on using but they have the smarts to understand both sides. In this case, on the Mac we will use Thunderbird, and on the Windows side, we will use either Windows Contacts (part of live mail in Vista and W7) or Outlook Express on an XP computer. The import/export protocol these go-between email clients both handle perfectly is called LDIF (use your favorite search engine to find out more about LDIF).
Note: I don’t actually consider WLM to be a high quality email client but it is very useful in this one respect.
Mac Side: On the Mac, Thunderbird is designed to import without error the Mac address book contacts when first invoked. Download and install the latest copy of Thunderbird, then answer affirmatively when prompted to permit access to Mac contacts. Now all the contacts should be in Thunderbird (including groups). Thunderbird uses an export mechanism for contacts called LDIF, which the Mac Address Book client does not offer. Open Thunderbird, check your contacts for any corruption, and then export all the contacts using LDIF protocol to a file. Put this LDIF file on a flash drive.
Windows Side: Take the LDIF file to the Windows PC and import the LDIF contacts file into OE (XP) or WLM (Vista/W7). All the contacts and groups should transfer perfectly. Exit the temporary email client. Then start Outlook, and import these contacts from WLM or OE to Outlook. Outlook should give you a choice of importing contacts from one or the other of these clients depending on whether the Windows PC is running XP or Vista/W7.
Your contacts should now be in Outlook, perfectly transferred with no errors. I did not test or check all possible contact fields, so it’s possible that some fields may not transfer properly. But I didn’t notice any errors with my data set.