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Microsoft Entourage Gets Spotlight and Sync

Microsoft has released the 11.2.3 Update to Office 2004. The 57 MB download incorporates all previous updates and service packs, so if you’ve neglected the care and feeding of your copy of Office 2004, now might be a good moment to mend your ways.


The Read Me file accompanying the download lists various minor bug fixes for Word, a stability fix for PowerPoint, and a security fix for Excel; but don’t go looking for your favorite pet peeve to be mended in this release. (None of ours were.) The emphasis of this release is on Entourage, with several bug fixes (such as improved calendar printing, meeting and event handling, and 10.4 Server connection support) plus two long-awaited new features: Spotlight support, and synchronization with Address Book, iCal, and iSync.

Spotlight — To turn on Spotlight support, choose Entourage > Preferences > Spotlight and check "Include Entourage items in Spotlight search results." You should then press the Rebuild button to create the initial Spotlight metadata files. After that, when you perform a Spotlight search, Entourage items are included in the results, and choosing a found item opens it in Entourage. For example, the top hit for "TidBITS#" on Matt’s machine is "TidBITS#820/13-Mar-06", the subject line of the most recently sent TidBITS issue; choosing it opens that email message in Entourage. Searching for "Engst" gives a top hit in the "Contacts" category of "Adam C. Engst", and choosing it opens Adam’s entry in the Entourage Address Book. Notes are also searchable (with the results appearing in the "Documents" category), as are Calendar Items and Tasks (with the results appearing under "Events & To Do’s").

Spotlight searching is implemented through an importer (stored in your /Library/Spotlight folder) and XML metadata files reproducing the contents of your Entourage database as individual items (in ~/Library/Caches/Metadata; Matt’s is now about 32 MB, about one-third the size of his database). Just to give you an idea of the possible power of a search on this material, the metadata for an email message’s Spotlight metadata file includes (along with its content) its date sent, its subject, its recipients’ names and email addresses, its sender name and address, and more than two dozen other bits of information. One’s overall impression, in short, is that the Microsoft folks have done this exactly right, and despite the extra hard disk space that the implementation requires, we’re not at all sorry to have the contents of the Entourage database (which is in a proprietary and always at-risk format) reproduced in a form that any text processor can retrieve.

Sync Services — Entourage’s use of its own internal Address Book separate from Apple’s Address Book has been a long-standing problem, to which the solution has traditionally been Paul Berkowitz’s excellent AppleScript scripts. Microsoft’s approach has the advantage of using Mac OS X’s Sync Services, which means that it’s much faster than AppleScript and works not only between machines (and even, in a very real sense, platforms) using .Mac, but also, even if you don’t subscribe to .Mac, it works on your own machine and (most important) it’s live, or nearly so. To start, choose Entourage > Preferences > Sync Services and check "Synchronize contacts with Address Book and .Mac". You’re offered a choice of replacing Apple’s Address Book contents with Entourage’s, or the other way around, or merging them. Merging can result in some duplicate items, but the good news is that all you have to do is resolve these duplicates in one place; changes in one address book are reflected almost instantly in the other.


When you set up Sync Services synchronization for events and tasks with iCal, on the other hand, Entourage creates an "Entourage" calendar in iCal, and that’s the only set of iCal events that it synchronizes with. This seems a reasonable approach. Conflicts are unlikely, and the use of different calendars within iCal gives you control over what’s read back into Entourage and what’s not. One downside, however, is that if you already have numerous items in iCal and you hope to move them into Entourage, you must select them (individually, or collectively using the list pane at the bottom of the window) and assign them to the Entourage calendar. Even then, because Entourage uses Categories and Projects to organize events and tasks, rather than separate calendars as iCal does, you may have difficulty maintaining a distinction between types of events and tasks that maps correctly between the two programs.

If you are a .Mac member and have the relevant checkboxes (Calendars and Contacts) selected in the Sync pane of .Mac System Preferences, your Entourage contact, event, and task data also sync with .Mac. This means you can access your Entourage Address Book (though not, alas, your calendars) via the .Mac Web site, and that you can synchronize the data with other computers you own, even if they don’t have Entourage on them. Entourage also adds a new item to the Sync list: Entourage Notes. Since there is no equivalent Apple application, synchronizing this data at present simply means making a backup copy of it onto the .Mac servers, as well as making it available to other Macs you own that have Entourage on them.

In addition to Apple software, other Sync Services-compatible products such as SOHO Organizer can now access your Entourage data (and vice-versa). Similarly, if you have configured iSync to synchronize data with your Palm device, cell phone, or iPod, your Entourage data now suddenly becomes available to these devices as well (possibly through a third-party conduit such as The Missing Sync).

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Unlike Apple Mail, which includes synchronization support for account settings, rules, signatures, and smart mailboxes, Entourage currently does no email-related syncing.

Overall, this seems on first meeting to be an extremely well conceived and implemented update. Entourage has suddenly become a far better Mac OS X citizen. With Spotlight searchability, Entourage users need no longer feel left behind by Mail users; with Address Book and iCal synchronization, they are no longer obligated to perform manual double-entry or risk forgetting which of two different venues contains a vital bit of information. There are some disappointments: Microsoft’s entire notion of Categories fails to cross the synchronization boundary, because it corresponds to nothing in Apple’s applications, and custom fields have the same problem. Nevertheless, it’s no exaggeration to say that a great weight has been lifted from the minds of Entourage users. To the Microsoft team that brought us this update: bravo.

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