Print Address Labels & Return Address Labels with OS X Address Book

If you want to print address labels for mass mailings, you cannot do that with Apple’s Pages, because Pages puts only one address per page in its mail merge function. This is fine, if you want to write a lot of identical letters to different people and also want to add custom printed envelopes. But If you don’t want to feed each envelope individually into your printer, you need address labels.

If you don’t want to buy third party software (see below), this can be done with Address Book. the problem here is, that labels can not be edited. You choose the contact(s), or group, and then select Print->Labels. After selecting the type of label, they can be printed directly, or send to a PDF, or to preview. If they don’t contain exactly the information you want, you must edit your information in Address Book; there is no way to edit the label information prior to printing.

If for instance you want to print a label to Toby and Spouse Junker, you would take the Toby contact and add Spouse Junker to the spouse field. If would only add Spouse to the spouse field, the label would read Toby Junker and Spouse. In other words, the label engine is smart enough to recognize the same last name.

This also works for partners with different last names, families, and children. However, you cannot use the other field, for it will be ignored. If you enter Family into the spouse field, the label would be made out to Toby Junker and Family., etc. If children are listed, they will be added, too. Depending on if the child’s last name is provided, it will show up either as Toby and Child Junker, or Toby Junker and Child. Finally, even spouse and child can be added at the same time. Again, depending on whether or not the last name is listed, it will be printed as Toby, Spouse and Child Junker, or as Toby Junker and Spouse and Child.

But now to the biggest mystery: How do you print return labels for yourself, that you put on the top left of the envelope. If you try it, you’ll find that it is not possible out-of-the-box. I even tried to create a new group and add myself to it several times. That does not work, because a unique contact can appear only once in a contact group. I found the solution in a post by Daniel J Greene in this Apple Discussion thread (paraphrased here for better legibility and with faster mouse and shortcut actions):

1. Select your card and drag it to the desktop.
2. Click it, and press Command-D 28-times to duplicate it for a total of 29 cards (assuming you want to print onto sheets with 30 labels such as the common Avery Standard #8160 ).
3. Then select these cards and drag them into the right-most panel of Address Book.
4. You will be warned that you are trying to import duplicate cards. Select “Review Duplicates”.
5. In the Reviewing Window, click “Apply to All” in the bottom left, and select “Keep Both”, then click OK.
6. Select all 30 cards (the original plus the 29 duplicates) and go to File->Print (or press Command-P) and follow the standard procedure to print address labels (see above).
7. For future use, save this as a PDF, and then delete the 29 duplicate cards.

This is a rather cumbersome work-around and I find it hard to understand that something like this should be necessary. Alternatives reported elsewhere in the same thread are to use Microsoft Word, or MacKiev Print Shop, but these are no alternatives for me, because I don’t want to spend the money for new software for just this little feature. For all my other word processing needs I use NeoOffice or Pages.