Another Way to Sync..... If iCloud Rains On Your Day, Google Has An Umbrella....

Apple's Cloud syncing service has been decidedly problematic in my three month evaluation period. My Windows and iDevice environment apparently represents a challenge for Apple. Mirroring a typical, "mixed use," environment, using a mixture of iDevices and Windows PCs, ostensibly, makes me the exact type of user this iCloud service is intended to help. In my evaluation, Apple's link between Windows based Outlook clients and iDevices seems particularly prone to errors. At times these syncing issues can be quite serious creating circumstances where a user's data can be at risk. At its most destructive, your data can be deleted without warning!

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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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. 

Music Row Tech will never sell, give away or use your personal information with third parties. 

All rights reserved @2012, Music Row Tech (MRT). Any reproduction without the author's consent is prohibited.

Is Apple Losing Its Mojo? The iCloud Has At Least A Few Raindrops....

Apple’s once seamless experience, the “it just works”  mojo which every fanboy has waved in front of Windows centric guys like me for years like a red cape in front of a bull,  is being bloodied of late. In many ways, it pains me to write about these missteps. You see after decades performing network support, coding for, and proselytizing the merits of the Wintel ecosystem (particularly for mainstream businesses of all sizes), I have embraced the Apple Kool Aid. For the past six years, I have advocated that Apple’s walled garden approach is a “better mousetrap” for many, especially for individual users and smaller businesses.  The  lack of mainstream malware issues alone more than offsets the TCO (total cost of ownership) equation for virtually this entire, massive, user community despite the premium you pay for that stylish Apple packaging and logo  on the front end.

The tipping point for me, and many others, has been the undeniably joyous mobile experience of the iPod, iPhone, and iPad.   I have used every iteration of iPhone and iPad on a daily basis and have been accused of working for Apple, or at the very least being a shareholder (which sadly I am not, then or now!). I have happily related the personal and professional productivity these tools have added to my life on hundreds of occasions since the earliest days of the iPhone’s debut.  My tales and ad hoc demonstrations are responsible for “selling” dozens and dozens of iProducts to family, clients, and even passing strangers.

So why do I sense the winds may be changing…? Let me cite this recent, “unApplelike” experience:

Authentication!  With the addition of iCloud and its at times confusing subsets—Photo Stream; iCloud Music/Match—Home Sharing and of course the Apple Store, log in issues are surfacing with great frequency and causing (real losses of productivity, not to mention frustration). Ironically, in many instances, it is the long term Apple faithful, experiencing the most frustrations.

If you happen to be beginning your trip into Apple’s garden today, authentication can be administered in a straightforward manner. Sign up following Apple’s rules for user name and passwords when you register your first Apple Product. When you purchase your second (and Apple hopes your third, fourth, ….) use the same user name/password log in combination. When you add a new service to your personal ecosystem such as iCloud, iCloud Music (and yes they are different), Photo Sharing, Home Sharing, use the same authentication!  Adhere to a few more caveats which are known issues but aren’t highlighted in Apple’s many getting started videos and tutorials.

 For instance, don’t try to share your devices and content libraries with your family members.  Think you and your daughter should be able to listen to each other’s music while sitting around the house through your family iPad or through the family iTV? After all, you (Dad) in all likelihood paid for all that great “99 Cent” song content no matter what Apple ID your kid was signed on as when s/he hit that all so easy, “Buy Now” button! No way, Pops! Not if you (very rationally)  gave your kid their own Apple ID to say keep track of  their online spending (after all what Dad wants to give their kid unrestricted “Buy Now” rights to their Apple tied AMEX card at age eight???) or for any of number of other valid reasons. Multiply this several fold if your nuclear family (and number of Apple Accounts) is  larger than my little two person household (discounting the dog who to date hasn’t gotten into this circus beyond chewing on an Apple charging cord several years ago). Or how about reading an eBook and wanting to share it with your family member? Not likely (this one you can assign blame to the print publishing world who is even further behind the twenty-first century curve and the folks down the street from me on Music Row  many of whom still are living in denial of the “new” digital music world in which they live. But this is a topic for another post.)

Don’t travel internationally (you can’t use the same credentials in Apple’s Japan iStore, as well as several other countries,  and in America). Again, certain legal issues make this separation necessary, but we expect Apple to solve these logistical hurdles for us, or at the very least make them well known "potholes," and not let us fall into these problems unwittingly!

You think everything you buy from Apple is yours to use on any device? You have to understand, it is your authentication, now really a verified email address, not your AMEX number, not even your Social Security Number, which is the glue holding your iCloud world together (or will tear it apart).

Problems, some severe, arise if you have multiple Apple IDs; happen to have an Apple ID which is not a fully qualified email address (such as “rwachs”) or have at one time accepted an Apple email account tied to the soon to be jettisoned, Mobile Me experience….?  If any of these situations applies to you, the promise of putting your life in Apple’s hands and servers can be filled with stormy iClouds….

Reports of “losing” access to at times years of paid content; improperly or non-synching of important, critical, calendar and contact information, and more have resulted from these issues. Add imposed DRM (digital rights management) constraints imposed by book and music content providers (and yes there are still plenty of hoops to jump through!) and the problems simply multiply! Even after sorting through the various user name/passwords governing:

•          Apple Store
•          iCloud Data (Contacts/Calendar/Bookmarks/etc.)
•          iCloud Music/Match
•          Home Sharing

across multiple devices including iPhones; iTvs; iPads; iPods and computer systems (including a Windows box running  the now aging iTunes software which remains the chief local “meteorologist” for this new iCloud  vision of your digital life), and I have vexing problems. After more than thirty days of “experimentation” with these services My iPad2 still insists that, “This Device is Already Associated With an Apple ID…. You can use iTunes Match on this device with just one Apple ID every 90 days. This device can be used with another Apple ID in XX days.”

Of course my iPad is associated with an Apple ID! Ironically, until very recently, you couldn’t even use an iPad2 without tethering it to an iTunes enabled computer and “phoning home” with an Apple approved account! I don’t even know which ID my iPad2 is unhappily tied to (when I purchased this unit the first day it was available almost a year ago I only had one Apple Account to associate)...  Frankly, I stand a very real chance of typing the “wrong” ID again when my 90 Day penalty box finally expires (which will put me into the summer of 2012 before I can play music or  synch a book or app, off this device again)! By the way, the iCloud process kindly erased all my existing music on this device before telling me it “isn’t eligible” for the newly purchased iCloud Music Account or other iCloud synching benefits!

To be fair, authentication issues aren’t “easy” to fix and merging accounts on the backend of complex databases can be a challenge. Google (I am currently  hold a long equity position in this company) struggled to get Google Docs users onto Google+ for several months (during this product’s beta period which is the time to explore these problems!) But Apple certainly has the engineering resources to resolve these issues and should have every motivation to do so as it is its most loyal base of long term users that are bearing the brunt of these problems.

I spent several hours sorting through these problems. I resorted to creating simple spreadsheets to identify and isolate which devices and log ins might be causing the problems I was experiencing. I even contacted Apple Support in an effort to “merge” my user name with the verified, primary, email address tied to this account, thinking this would solve some of the issues. After an hour’s conversation and some internal discussion I wasn’t privy to, I was able to make my primary email, rwachs@musicrowtech.com my default Apple ID—my ten plus year, “rwachs” user name was not accepted by one or more new Apple services which require a fully qualified email address. This did resolve some, but not all, of my connectivity/synching issues.

All told, I spent about eight hours troubleshooting, researching, and contacting tech support on these issues alone. The $25 annual iCloud Music charge, bandwidth, upload time, and other costs are strictly incidental to my time and yes, “frustration.”  If these inconsistencies between new Apple products  prove vexing to someone with nearly thirty years of IT experience, I can only imagine what some of the less computer savvy—including  many of those I have encouraged to move  to Apple’s ecosystem through the years!—must be experiencing. Judging by Google searches and support forum posts I have read in an effort to understand my problems, I am far from alone.

Apple, with Steve Jobs at the helm over the past couple of decades, has built what is arguably the premiere technology company, not to mention the most highly valued worldwide corporation, by building wonderful products which “just work.” Whether it is reaching for the next new thing (e.g. cloud computing), pushing a product out the door prematurely (with the exception of Siri, Apple is not known for releasing products into “the wild” in beta), or simply striving to appeal to an ever growing audience beyond its core constituency Apple fan base, iCloud seems to be the first major endeavor in quite some time to leave Infinity Loop not quite ready for prime time…. Stay tuned for more.

How has iCloud impacted your life?  Have you had a smooth transition? Can you not live without the cloud in your life? Not live with it!? Please share your thoughts….

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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