While calendar sync seems slightly more stable than contact synchronization, even this service presents some perplexing issues. When setting up Apple's iCloud with Microsoft's Outlook calendar, the install insists on creating a unique copy of your primary calendar information. This iCloud calendar must become your primary Outlook calendar view, but it has limitations. Reminders and repeating events either do not work or throw up error messages. Worse, in my tests, repeating events such as birthdays, anniversaries and the monthly recycle pickup, either do not get copied to this new "iCloud" copy or seem to randomly get copied multiple times between your various "synched" calendars, creating multiple events across your Outlook file and iDevices. The end result of this process is you can (and in my case would) miss future events if you don't check both your primary Outlook calendar and its iCloud counterpart (which of course completely dispels any motivation you may have for transferring critical details of your life to Apple's Cloud Service).
The requirement to duplicate your entire calendar in order to place it in the "iCloud," with all its attendant limitations (such as repeating events ONLY being able to be posted to your primary calendar which cannot be your iCloud calendar!), is particularly perplexing because Google's sync process doesn't require this duplication and therefore circumvents these limitations! What's more, Google has very servicable, free, sync tools which work with your current Outlook profile.
Contact information seems more complex and even more prone to error. Apple's service took hours to sync the first time with my admittedly large 1,000 plus contact database which spans 25 years. The result? Massive duplications! In many cases, contacts with only Company Name (e.g. "American Airlines") were duplicated a dozen or more times; contacts with a first name (e.g. "Randy") get similar duplicative treatment. Other, seemingly even more random, duplications swelled my Outlook Contact database from 1,000+ database to well over 4,000!
Worse, as this iterative process unfolded, one seemingly logical step I took was to sign out of iCloud services. (If you are unfamiliar, to get iCloud on a contemporary Windows box requires a `separate "app" in your Task Bar in order to keep synchronization "current.") When I signed out of the iCloud Windows application, without any warning!, my 25 years of contacts were deleted from my local Outlook PST file!!!
So two bits of advise before moving forward!:
- If you are going to experiment with Apple Cloud Sync, or any other sync service, BACK UP YOUR OUTLOOK DATA before proceeding! Often this admonition is a boilerplate precaution you may, or may not, even read before proceeding. In this case, you should follow the "recommendation" very literally, your data is at risk!
- Take a second to export your calendar and contact data separately. Multiple backups are always good, when working with cloud based services and with sensitive data, multiple backups are a must! If you are unclear about how to back up your Outlook data there are many great online "how to" articles on the subject including this post.
So what is my conclusion? Whether you are an Apple fanboy, a Microsoft afficianado, a diehard Googler, or just someone ready to enjoy the benefit of having your data available on any device, anywhere, always current, iCloud is not a stable alternative at this point. Google is a better partner to this dance....
Google has managed to remain device agnostic, providing solid iOS Apps for iPhone and iPad users, unsurprisingly, has great Android apps, while at the same time providing rock solid Google Calendar and Google Contact applications which run in any modern browser. The company also provides synchronization tools such as Google Calendar Sync which allows one way and two way syncing using Outlook's default calendar. For many, these free tools will be more than sufficient. This landing page offers step by step instructions and tools for synchronizing your mail, calendar and contacts with a variety of devices.
If you want greater control, or want to expand your synchronization options to include Evernote, Dropbox, Nozbe and more, the Gsyncit Utility is superb. This application is not free. Currently, the developer is charging $19.99 (or $4.99 for a major update from an earlier release). I have used Gsyncit for several years and have found the developer extremely responsive. (There have been points in time when the number of updates pushed out has almost been overwhelming, but behind the scene changes in Google's databases has made the updates necessary and it is admirable that issues are promptly addressed.)
Gsyncit can be tried for free before purchase. It is simply the most robust synchronization tool I have found. Highly recommended. Here's a partial list of its features:
- ONE and TWO WAY syncing of Outlook calendars, contacts, notes and tasks.
- Sync with Google, Dropbox, Simplenote, Toodledo and Evernote
- MULTIPLE ACCOUNTS: Sync with multiple Google, Toodledo, Dropbox, Evernote, and Simplenote accounts and works with multiple Outlook profiles
- SYNC MULTIPLE COMPUTERS: Sync multiple computers using Outlook with a single Google account (gSyncit license required for each computer)
- MATCHING LOGIC: Automatically matches entries to prevent duplicate items when syncing.
- AUTOMATIC SYNC: Automatically sync items on a regular interval, between certain hours of the day, and/or when Outlook starts/exits.
- DETAILED CONFIG: Detailed sync options to control how and what you want to sync.
- FILTERING: Keyword and category filters to control the Outlook content you want to sync.
- CATEGORY SYNC: Advanced options to sync Outlook categorized items with Google, Toodledo, Evernote and Simplenote.
How are you synchronizing your critical mail, contact and calendar data? What is your experience with iCloud and Microsoft Outlook? Please share your thoughts through the comment section below.
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I currently participate in the Amazon Associates Program and certain item links included within this post may tie to this affiliate program.
I have a long position in $GOOG
Companies: Apple, Google, Gsyncit
This commentary is not meant as an endorsement of any company or to provide financial advice. If the author has any financial interest in any company mentioned at the time of this article’s posting, it will be explicitly noted. I welcome feedback and comments.
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