Could Microsoft Stage a Comeback Against Apple?

NEW YORK (TheStreet) -- The thesis of this article is that Apple's (AAPL) recent cloud-securityissues could pose an opening for Microsoft (MSFT).

I'm approaching the issue at hand from a regular consumer'sstandpoint. The average American today is increasingly signing up fora "total cloud experience" with at least one of the major ecosystems: Google ( GOOG), Microsoft or Apple. There are also the three smallercomputing ecosystems: Amazon ( AMZN), Facebook ( FB) and BlackBerry ( BBRY).

In an increasingly typical case, a user of these major ecosystems isstoring most of the following information in the respective cloudverticals provided by Google, Apple, Microsoft and others: email/SMS, address book, calendar, documents, telephone records, music/video multimedia and books.

If you consider the information contained in particular in the firstfour of those categories above, the stakes are high to keep thesesystems secure. During the last year, however, there have been avariety of security breaches that illustrate the weakness of some ofthese cloud security systems:

1. Mat Honan:

In this hack last August, a prominent Wired magazine journalist's --Mat Honan -- life was taken over. The chief weaknesses in the systems to enable this came from Amazon and Apple, where Honan's iCloudaccount was hacked and caused the criminal to remotely wipe his Applecomputers, and worse.

2. Apple's iCloud left the gate open:

More recently, on March 22, it was discovered that anyone could getinto your iCloud account by just knowing your email address and yourdate of birth -- easily obtainable online by any hacker worth his orher salt. Within hours, Apple shut down its iCloud password resetsystem -- or at least so it thought.

Concerned Apple customers who went to iCloud to look into theiraccounts had the option to turn on so-called "two-factorauthentication" -- which basically adds to cloud account passwordsecurity by sending a separate code by SMS to your phone. However,Apple responded by saying it needed 72 hours to implement thissecurity measure.

Well, for people who instructed iCloud to activate this securitymeasure on March 22, it took a whopping 13 days for Apple to enableit. A hacker doesn't need much more than 13 seconds or 13 minutes todestroy someone's life.

3. Broader issues with Apple's iCloud:

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

As many people have been finding out over the past 18 months, iCloudremains far from perfect. How many people you know have had problemswith 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 campaignstrategist Mark Penn, Microsoft has been focusing its advertisingattacks 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 morerelevant ads.

Leaving aside that Microsoft too must be reading your emails, if it isto have a good spam and malware filter, the "Scroogled" theme has notworked because most people welcome the idea of getting more relevantads, even if some Google server technically "reads" your emails.

During this misguided Scroogled campaign, it appears that Microsofthas continued to lose ground to Google on a daily basis: Gmail iscatching up with Hotmail/Outlook, Google Docs is free and taking sharefrom Microsoft Office, Android is approaching 70% market share, orclose 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 superiorability to serve you relevant ads, and instead investigate whether itcan 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 andMac to avoid using iCloud at least to some degree. And some Appleusers put all of their documents, contacts, calendar, email and soforth into iCloud. This is potentially a fat target for Microsoft.

Objectively speaking, is Microsoft's cloud security more secure forthe average consumer than Apple, let alone Google? That's a complexset of issues, and it's not clear there is an objective answer here.It's also a moving target.

Some people will argue that one of the most notorious IT securitydisasters have been the Windows PCs. That's certainly true, but keepin mind two things here:

1. Microsoft's security has improved a lot since the XP and Win 7days. Windows 8 is a huge improvement.

2. We are not talking about the security of the PC here. We aretalking about cloud account security. You could have a pristinelymaintained and virus-free PC, but it wouldn't matter at all if somehacker manages to reset your cloud account password.

What about Google? Google is the ultimate in cloud-centric. Itsservices are designed from the cloud out, and it shows in terms of theease of use and integration. It also seems like Google has anexcellent security record. Google even invented a new PC operatingsystem -- Chrome OS -- in order to protect its workers better thanusing Windows or Mac.

Is Apple really that insecure? Who is to say? We know the problems Icited above. Someone like Mark Penn has never been shy about making abig issue about a small accusation or suspicion. Likewise, if anadvertising attack were to boomerang back into Microsoft's court, hecould help it bounce away as if Microsoft were made from teflon: Itsure worked for the Clintons!

Microsoft is doing many of the right things. Later this year, it willexecute on "the grand unification" of all of its platforms -- PC,phone, tablet, Xbox and more -- onto a new version of Windows 8. Itis within reach for Microsoft to catch up with much of what Apple andGoogle have been doing, and to regain the initiative again.

I think Microsoft's better case is to go after Apple -- not Google --and its best way of attack could be to claim it has better security toprotect the average consumer's cloud account. Whether in the end thisis objectively true or not -- at least it would give Microsoft theopportunity to play on offense, for a change.

At the time of submitting this article, the author was long GOOG, FBand AAPL, and short MSFT.

This article was written by an independent contributor, separate from TheStreet's regular news coverage.

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