2. RealNetworks RealPlayer (1999)

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A frustrating inability to play media files–due in part to constantly changing file formats–was only part of Real’s problem. RealPlayer also had a disturbing way of making itself a little too much at home on your PC–installing itself as the default media player, taking liberties with your Windows Registry, popping up annoying “messages” that were really just advertisements and so on.

And some of RealNetworks’s habits were even more troubling. For example, shortly after RealJukeBox appeared in 1999, security researcher Richard M. Smith discovered that the software was assigning a unique ID to each user and phoning home with the titles of media files played on it–while failing to disclose any of this in its privacy policy. Turns out that RealPlayer G2, which had been out since the previous year, also broadcast unique IDs. After a tsunami of bad publicity and a handful of lawsuits, Real issued a patch to prevent the software from tracking users’ listening habits. But, less than a year later, Real was in hot water again for tracking the habits of its RealDownload download-management software customers.

To be fair, RealNetworks deserves credit for offering a free media player and for hanging in there against Microsoft’s relentless onslaught. We appreciate the fact that there’s an alternative to Windows Media Player; we just wish it were a better one.

3. Syncronys SoftRAM (1995)

Back in 1995, when RAM cost $30 to $50 a megabyte and Windows 95 apps were demanding more and more of it, the idea of “doubling” your system memory by installing a $30 piece of software sounded mighty tempting. The 700,000 users who bought Syncronys’s SoftRAM products certainly thought so. Unfortunately, that’s not what they got.

It turns out that all SoftRAM really did was expand the size of Windows’s hard disk cache–something a moderately savvy user could do without any extra software in about a minute. And, even then, the performance boost was negligible. In the U.S., the Federak
Trade Commission dubbed Syncronys’s claims “false and misleading”, and the company was eventually forced to pull the product from the market and issue refunds. After releasing a handful of other bad Windows utilities, the company filed for Chapter 7 bankruptcy in 1999. It will not be missed.

4. Microsoft Windows Millennium (2000)

This might be the worst version of Windows ever released–or, at least, since the dark days of Windows 2.0. Windows Millennium Edition (a.k.a. Me, or the Mistake Edition) was Microsoft’s follow-up to Windows 98 SE for home users. Shortly after Me appeared in late 2000, users reported problems installing it, getting it to run, getting it to work with other hardware or software and getting it to stop running. Aside from that, Me worked great.

To its credit, Me introduced features later made popular by Windows XP, such as system restore. Unfortunately, it could also restore files you never wanted to see again, like viruses that you’d just deleted. Forget Y2K; this was the real millennium bug.

5. Sony BMG Music CDs (2005)

When you stick a music CD into your computer, you shouldn’t have to worry that it will turn your PC into a hacker’s plaything. But that’s exactly what Sony BMG Music

Entertainment’s music discs did in 2005. The discs’ harebrained copy protection software installed a rootkit that made it invisible even to antispyware or antivirus software. Any moderately clever cyber attacker could then use the same rootkit to hide, say, a keylogger to capture your bank account information, or a remote-access Trojan to turn your PC into a zombie.

Security researcher Dan Kaminsky estimated that more than half a million machines were infected by the rootkit. After first downplaying the problem and then issuing a “fix” that made things worse, Sony BMG offered to refund users’ money and replace the faulty discs. Since then, the record company has been sued up the wazoo; a federal court judge recently approved a settlement in the national class action suit. Making your machine totally vulnerable to attacks–isn’t that Microsoft’s job?

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