Printing Mailing Labels and Envelopes from Address Books and Spreadsheets

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I recently spent some time researching how to print mailing labels and envelopes for a family member. I found that depending on your configuration the process could be simple or frustratingly complex. It is the time of year where many people are still agonizing whether or not they should send tardy holiday cards or last minute New Year’s cards. If this description fits you or you want to print labels or envelopes for another reason, read on, and hopefully I will be able to give you some tips or software recommendations to make the process go faster and more smoothly.

I primarily investigated printing labels and envelopes from the Mac OS X Address Book, but along the way I found a number of other solutions for the Mac, Windows, as well as options to generate label sheets on the Web.

Generating label sheets from the web, no software needed

The Avery Design and Print Online service is a free tool (registration required) that allows anyone to create label sheets online and download them as PDF suitable for printing. In order to use the online tool, you will need to export your address book as a CSV. How to do this can vary greatly depending on which system you use. For example, Apple Address Book cannot export directly to CSV, only to vCard and the Address Book Archive backup file. Microsoft Outlook can export addresses into a CSV file.

FileMaker Bento 3 ($50) can open the Apple Address Book directly and export it to a number of formats including CSV. Address Book to CSV Exporter can export the entire Apple Address Book or groups to CSV. It’s free and open source. There are a number of additional packages that offer additional flexibility for exporting from Apple Address Book. I’ll address those in a future article.

Mac OS X and Apple Address Book

My original goal was to figure out how to generate labels from data that was both stored in Apple Address Book and in spreadsheets. The Mac OS X Address book has built in functionality to print Avery Standard, Avery A4, and DYMO type mailing labels. Apple has two primary documents that discuss printing labels and envelopes. The documents are clear and useful, but surprisingly hard to locate either in the local Help Viewer or on Apple’s support site. Both documents have been recently updated for Snow Leopard and may be more up to date than versions in the local Help Viewer. The first document, AddressBook 5.0 Help: Printing, is a brief and useful introduction. The second document, Address Book: Printing mailing labels or envelopes with multiple names, covers a topic that people clearly find confusing given the number of posts to various support forums.

Tech Talk Point has a longer introduction with screenshots to better explain the process with their page on Printing Labels, Mailing List & Envelopes in Mac OSX with Address Book

PostCheck ($10) is a great little plugin for the Mac OS X Address Book by Brian Toth that will look up and add missing zip codes (and optionally zip+4 codes) to address book entries. PostCheck will can also bulk validate addresses and reformat address to conform to preferred USPS guidelines.

If the Apple Address Book does not print labels as you wish, you still have a number of options, some of which offer additional flexibility over the built in features.

• Microsoft for Mac Office will print labels and envelopes using a mail merge in Microsoft Word with an address list stored in Microsoft Excel.

• The Print Shop for Mac , $70, from Software MacKiev can print envelopes and Avery, CD Stomper, Memorex and NEATO labels using address taken directly from Apple Address Book. The application makes it simple to add graphics to labels.

• pearLabelizer from pearworks is a free application that can take contacts or groups of contacts directly from the Mac OS X Address Book. It has an option to print individual labels from plain text using the Services Menu.

• EasyEnvelopes from Ambrosia is a free Dashboard widget for printing envelopes. The EasyEnvelopes is attractive and straightforward to use. It integrates with the Apple Address book and includes support for USPS bar codes.

• Apple Pages can print mailing labels using free label templates from Avery. This MacFixIt article, How-To: Using label templates in Pages, provides a step by step guide. My recommendation is to try the free Avery Design and Print Online service first, although you will need to export your contacts as CSV.

• The iWorkCommunity Templates Exchange section on labels includes a variety of additional label types. The templates are free.

• Avery DesignPro for Mac is a free application for designing labels, business cards, greeting cards, and many other types of print work. The application is a large download and can be somewhat unstable. Like the online version, you will need to export your address book as a CSV file. I would recommend trying the online version first.

Microsoft Windows

Microsoft Windows users will likely find that using a combination of Microsoft Word and Excel or Outlook is the easiest path to printing mailing labels. The following support documents on the Microsoft Support site clearly describe how to create mailing labels and envelopes using the mail merge functionality of Microsoft Word with data stored in Microsoft Outlook or Microsoft Excel. The examples provided are for Office 2007, although similar documents are available for older versions of Microsoft Office.

• Create and print labels for a mass mailing - Word

• Create and print labels for a single item or address - Word

• Create and print envelopes for a mass mailing - Word

• Demo: Create a set of labels with mail merge - Word

• Avery offers several products for windows including Avery DesignPro and Wizard for Microsoft Word in addition to their online product.