Imagine doing business with a company that compiled information about your political convictions, religious beliefs, health, and family. Now imagine that this company turned around and made such information, along with your name and hometown, freely available to the rest of the world.

If you've purchased something on, you've dealt with just such a company. The culprit is Amazon's Wish List, a tool that lets you build a list of books and other items you might be interested in checking out. Such lists can be viewed by anyone, unless you take an extra step to specify privacy. Indeed, it's possible to use the Wish List information to create databases of apparent liberals, gun owners, teenage girls, and so forth, and even to map them by location.

I'm not going to go off on privacy here. As far as I'm concerned, anyone who Web-surfs, gives out his or her name online, or buys things, and then still has an expectation of privacy is either clueless or a whiner. My point is that Amazon, a premium Internet brand and a much-admired company, hasn't done anything obviously wrong. The Wish List is a great feature. Yet the company was splashed with a bit of digital mud a few months ago when the feature's vulnerability to mass profiling was highlighted on Applefritter, a website aimed at Apple computer users. The item was then widely circulated around the Web, where it elicited a chorus of disapproval. One person called the Wish List "an invasion of privacy that could cast the shadow of suspicion onto ordinary, law-abiding people."

The simple fact is, figuring out what is ethical--a challenge under any circumstances--is getting trickier in the Internet age. As technology in general and the Internet in particular bring us more marvelous tools at an ever-increasing pace, companies are finding that moving toward the leading edge can earn them a black eye from some affronted segment of the online public. It's not just sensitivity about privacy but also free speech, marketing tactics, and a range of other issues. "With new technology comes new exposures," says Vivian Weil, a professor of ethics at the Illinois Institute of Technology. "There are new opportunities for companies to intrude one way or another on what people think is right, and these pitfalls are unfamiliar."

Just ask Sony BMG. In an effort to be proactive rather than just litigious in limiting illegal online music swapping, the label late last year tried something new: music CDs that when placed in a customer's computer installed a program to prevent the copying of songs. Companies have been adding antipiracy features to products for years, so what's wrong with that? Everything, according to an outraged mass of music fans. Installing software programs--even (or perhaps especially) one aimed at protecting intellectual property--without explicit user permission turned out be crossing the line. Even worse, the software made computers vulnerable to viruses. Sony quickly backed down and offered a program to remove the first one. But it just ended up making things worse when the new program was found to have similar security flaws.

Other recent examples: Best Buy was flamed by customers angry that prices they had seen advertised on the company's website--prices that can fluctuate hour to hour--didn't always match those in stores. Wal-Mart was smeared when its online store started recommending that buyers of the DVD Planet of the Apes also consider movies with African American themes. Even Google, celebrated for its "Don't be evil" motto, has taken some blows--for restricting the use of video clips it displays on its site, for example.

You don't have to be a big-name company to get bitten. B&H Photo-Video, a brick-and-mortar camera and electronics retailer based in New York City, has a solid reputation among online buyers. Henry Posner, B&H's communications director, responds to nearly every negative comment about the store, apologizing for screwups and explaining the company's side of the story when he feels a customer is being unfair. It sounds perfectly reasonable, but B&H has been blasted by online commenters who accuse the company of trying to dilute criticism inappropriately. "I aspire to be diplomatic," says Posner. "But there are people who will yell and scream no matter what I post."

How do you avoid being cast as the villain in the Web community's view of the world? Learn from others' mistakes. Here's a quick rundown of some of the ways you could run off-course in the blurry, dynamic, and sometimes no-win world of high-tech business practices. Note that in most of these cases, the companies could reasonably argue that they didn't do anything wrong--but lots of angry people begged to differ and were not shy about spreading the word.

Enabling evil You don't have to do anything bad yourself to find yourself in trouble: It's enough to inadvertently provide others with a means for shenanigans. Amazon's Wish List vulnerability is a good example. Google got dragged into that one, too, because, as Applefritter noted pointedly, the search engine's online mapping capabilities can be enlisted to create a map that shows the locations of, say, Wish Listers interested in books on Mao Zedong or Osama bin Laden. EBay gets into similar trouble. Buyers ripped off by unscrupulous sellers often blame eBay for their woes, even though the site has little way of policing the millions of transactions that take place on its pages and clearly states so. "It's not enough to say caveat emptor, we're just the bulletin board," says David Gebler, president of Working Values, a business ethics strategy and training firm in Sharon, Massachusetts. "That's just not acceptable anymore."

Problematic products Any company can release a product with problems, but technology is creating ever more ways to slip up, raising the stakes of errors. I-O Data, a Japanese maker of data-storage products, released a new external hard drive padded to prevent data loss if the drive is dropped. But the company unintentionally threw in a little bonus feature with the disk's software: a worm written by malicious hackers that can infect a customer's PC and force it to act as a spam distributor. Fortunately, the company caught the problem in time to avoid a widespread outbreak. LucasArts got dinged sharply when it performed a heavy makeover on its online game Star Wars Galaxies. The changes were intended to attract new players, but current gamers were enraged, claiming it invalidated their huge investments in playing time; one blog even noted that the new version excluded some disabled players because, unlike the old version, it can't be played with one hand.

Muzzling anything You have a right--nay, an obligation--to stop people from using your products and services to break laws, corrupt youth, and commit offensive acts, don't you? Maybe, but try explaining that to Web users who are fanatical about free speech online, no exceptions abided. Thus the popular MySpace website has drawn heat for censoring references to a rival service. Wikipedia, the online encyclopedia for which anyone can write and edit entries, drew criticism for some of the gross inaccuracies inserted by anonymous and occasionally malicious contributors. In response, the organization started to crack down on who could and couldn't contribute--which then drew sharp criticism from those who felt Wikipedia was betraying its wide-open-to-the-community mission.

No matter how careful you are, it may be impossible to avoid stumbling across some newly drawn ethical line. So be prepared to do some damage control when you get smacked down.

You could get into a Talmudic discussion about right and wrong in these situations. But it seems to me there are two practical keys here. First, recognize how slippery technoethics has become, and give more thought to the implications of every move. Involving as many constituents as possible--customers, suppliers, even random representatives of the online community--in decision-making is one way to increase the chances of catching a potential perceived ethical breach. And second, accept that no matter how careful you are, it may be impossible to avoid stumbling across some newly drawn ethical line, and be prepared for damage control when you get smacked down. "If a company comes out and explains why it did what it did and describes its process for addressing the problem, people respect that," says Gebler. "You can judge an organization by its first response to criticism."

David H. Freedman, a Boston-based writer and Inc. contributing editor, is the author of several books about business and technology. (