Could Microsoft Stage a Comeback Against Apple?

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

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

In an increasingly typical case, a user of these major ecosystems is storing most of the following information in the respective cloud verticals 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 first four of those categories above, the stakes are high to keep these systems secure. During the last year, however, there have been a variety of security breaches that illustrate the weakness of some of these 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 iCloud account was hacked and caused the criminal to remotely wipe his Apple computers, and worse.

2. Apple's iCloud left the gate open:

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

Concerned Apple customers who went to iCloud to look into their accounts had the option to turn on so-called "two-factor authentication" -- which basically adds to cloud account password security by sending a separate code by SMS to your phone. However, Apple responded by saying it needed 72 hours to implement this security measure.

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

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.

Objectively speaking, is Microsoft's cloud security more secure for the average consumer than Apple, let alone Google? That's a complex set 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 security disasters have been the Windows PCs. That's certainly true, but keep in mind two things here:

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

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

What about Google? Google is the ultimate in cloud-centric. Its services are designed from the cloud out, and it shows in terms of the ease of use and integration. It also seems like Google has an excellent security record. Google even invented a new PC operating system -- Chrome OS -- in order to protect its workers better than using Windows or Mac.

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

Microsoft is doing many of the right things. Later this year, it will execute on "the grand unification" of all of its platforms -- PC, phone, tablet, Xbox and more -- onto a new version of Windows 8. It is within reach for Microsoft to catch up with much of what Apple and Google 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 to protect the average consumer's cloud account. Whether in the end this is objectively true or not -- at least it would give Microsoft the opportunity to play on offense, for a change.

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

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

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