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Could Microsoft Stage a Comeback Against Apple?

Stocks in this article: AAPL MSFT

3. Broader issues with Apple's iCloud:

Actual security loopholes in Apple's cloud services are one thing, but they may be a reflection of all the other problems with iCloud. You might recall how Steve Jobs, in one of his final presentations, introduced iCloud whilst admitting that its predecessor system -- -- had failed to "just work." Jobs had scolded his engineers for the failure to achieve flawless cloud synchronization.

As many people have been finding out over the past 18 months, iCloud remains far from perfect. How many people you know have had problems with synchronizing their Apple address books from device to device, via iCloud? If Apple can't synchronize your address book correctly, how can you trust it to keep your account secure?

Microsoft: Is this the opening?

Under the direction of Clinton's highly political long-time campaign strategist Mark Penn, Microsoft has been focusing its advertising attacks on Google and the so-called "Scroogled" theme. In essence, Microsoft is making its case by attacking the fact that Google is "reading your emails" (among other things) so as to show you more relevant ads.

Leaving aside that Microsoft too must be reading your emails, if it is to have a good spam and malware filter, the "Scroogled" theme has not worked because most people welcome the idea of getting more relevant ads, even if some Google server technically "reads" your emails.

During this misguided Scroogled campaign, it appears that Microsoft has continued to lose ground to Google on a daily basis: Gmail is catching up with Hotmail/Outlook, Google Docs is free and taking share from Microsoft Office, Android is approaching 70% market share, or close to 20 times Microsoft's mobile market share, and so forth.

Perhaps Microsoft has picked the wrong target, and the wrong issue? Perhaps Microsoft should stop obsessing about Google's superior ability to serve you relevant ads, and instead investigate whether it can scare people into believing that using Apple's cloud services (iCloud) is one big security risk instead?

After all, it's almost impossible for someone using iPhone, iPad and Mac to avoid using iCloud at least to some degree. And some Apple users put all of their documents, contacts, calendar, email and so forth into iCloud. This is potentially a fat target for Microsoft.

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