Some things go together better than others. A piano plus an orchestra yields a piano concerto. An electronic synthesizer with drums, guitars, and vocals, might create a rock band. Switch it around—put the piano with the band, or the synth with the orchestra—and you’ll get an entirely different sound.
Pairings matter in the software world, too. Both Microsoft and Google offer systems to manage email, calendar items, tasks, contacts, and notes. But Microsoft Exchange works best with Microsoft Outlook, while Google Apps works best with Google’s Chrome browser. Each company “tunes” their software to work well within their own ecosystem.
Google Apps Outlook Sync for Microsoft Outlook connects Outlook on the desktop to Google Apps in the cloud. The sync software is like the piano sound on a synthesizer: it sounds like a piano, but isn’t a piano. Google Apps Sync lets you use Outlook mostly like Outlook…but not entirely.
The core Microsoft Outlook features work, of course: Emails sync, calendar items sync, contacts sync, and tasks sync. Even Outlook Notes sync to Google Drive as individual text files.
But not everything works. Google offers a complete guide online, but you’ll do well if you just know the following four items.
1. Some “Outlook-only” information won’t sync
Categories in Outlook, for example, don’t sync to Google Apps. Gmail uses folders and labels to organize email, not categories. If you rely on categories and switch back and forth between Outlook and Gmail in the browser, that may be a challenge.
Email drafts created in Outlook also don’t sync. If you’re in the habit of starting an email in Outlook, then moving to the browser, this may present a problem. On the other hand, if you work with Outlook all day—this may not affect your workflow.
Tasks sync, but some task details won’t. Outlook offers start dates, progress status tracking, and task reminders, none of which sync to Google Tasks.
2. Contacts within the Outlook Contacts folder sync
...But only contacts in the Outlook Contacts folder sync. Other contact information, stored outside of the Contacts folder, won’t sync. Keep your contacts in the Contacts folder—and update contact info there—and you’ll be fine. (Calendar information works similarly: calendars not in the Calendar folder won’t sync.)
3. Rules and Signatures
Neither Outlook rules nor Outlook signatures sync.
Instead of rules, create filters in Gmail. A filter may move, label, delete or otherwise handle incoming mail based on criteria you set. Gmail will apply the filter in the cloud, with the resulting changes syncing down locally to Outlook.
Unlike Outlook, Gmail supports only one signature—and legacy signatures from Outlook aren’t imported or synced. Within Outlook, you may create a signature that will work when emailing from Outlook. (Pro tip: Canned Responses, a Gmail labs feature, allow multiple signatures—and templated emails.)
4. Emailing to Groups
Personal distributions lists in Outlook don’t sync. You may use them, but the list will only be available from Outlook.
Create a Google Group to send email to sets of people. Each Google Group will have a unique email address: create a contact with the name of the Group, and add the Group’s email address. Sending an email to that address will then distribute the email to all members of the Google Group.
You—or an administrator—may configure Google Apps Sync for Microsoft Outlook to auto-update. Or, check for updates directly online.
For many users, Google Apps Outlook Sync offers a way to continue to use Outlook. As long as the sync features you need are supported, you’ll be happy. But if a key feature is missing, or doesn’t work as expected, that’s when frustration strikes. Troubleshooting can be difficult: is it a problem with Outlook? With an Outlook add-in? With Google Apps? With the Google Apps Sync software? Keep your backups current—because sync errors may cause significant headaches.
In the long term, the most elegant solution is to adopt Chrome and access Google Apps for your browser. Until you make that switch, you’re a bit like the synthesizer emulating a piano: workable, but never perfect.
(Addendum: In 1984, Ray Kurzweil invented one of the first synthesizers to emulate piano sounds successfully. He’s now at Google, where he works on natural language understanding. Separately, he’s a proponent of the ultimate backup: a backup of life itself. Backupify does not yet offer such a service.)
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