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The internet loves a marketing disaster. It makes few allowances for the brands that try and fail. It never forgets. And it rarely forgives.

The dreadful irony of these digital catastrophes is that they frequently befall companies that are doing their best to innovate. If Skittles hadn't been attempting to engage with user-generated content, it would never have exposed itself to the nasty reality check that forced a rapid rethink of its social media strategy. In other cases, such as the deathless ‘Dell hell' saga - which began in June 2005 when a disgruntled blogger took the computer giant to task over its poor customer service and faulty hardware - the brand well and truly had it coming.

As the scope of the web increases, a growing roll-call of brands have a digital marketing disaster against their name. One of the latest to join the list is Habitat, which learned a brutal lesson about Twitter hashtags in June. In the process, the furniture retailer handed a useful tutorial to any brand contemplating an exciting social media adventure.

For that reason, no brand should be utterly condemned for fouling up in its attempts to master a new medium. Each incident illustrates a different rule of engagement, and in many cases, those rules need to be broken in order to become apparent to all. While the unlucky brand spends a few days in the digital stocks taking a squishy bombardment from the online community, its mistake is written up in the annals of common-sense digital marketing, and no one has to make it again.

In hindsight, some initiatives, such as ask.com's faux guerrilla ‘Information revolution' campaign from 2007, seem to have been destined for ridicule. But the notoriety of these well-known bodge-jobs tends to mask the fact that brands frequently get away with terrible clangers when no one is really looking.

To help you avoid making such blunders, we bring you six of the biggest digital marketing messes of all time. Perhaps unsurprisingly, most relate to brands making a hash of social media.

Social media Habitat

Habitat won't be repeating the trick of using
bad-news-related hashtags to drum up interest on Twitter. In June it was caught piggybacking searches for ‘Iran' and ‘Moussavi' during the country's post-election riots. A predictable storm quickly picked up, online and off, and Habitat moved to distance itself from its own strategy, blaming ‘an overenthusiastic intern' who was, we were assured, ‘no longer associated with Habitat'.

But while the initial Twitter mix-up could be put down to mild cynicism and naivety from a brand getting to grips with a new platform, there are those who believe the real sin was Habitat's reaction to the outcry.

"Once you have been caught out, you need to admit culpability, and that is where you might regain a bit of the kudos you lost with the original campaign," says Garrett Dearey, associate director at Positive Digital. "Clearly it was a mistake and Habitat owned up to it very quickly, but blaming the intern and sacking them was unnecessary. If you are caught out, stick your hand up, say it was an initiative that didn't go well and try to make some degree of compensation, where possible."

User-generated content Skittles

In some respects, a brand like Skittles should be hailed as a hero of digital marketing. Yes, it made mistakes in throwing open its homepage to
social media feeds, but it messed up while trying to do something new, and then it amended its approach and stuck with its original strategy.

In March, the Mars-owned brand moved to harness the energy of social media, replacing the typical corporate bumf on its website with Skittles-related feeds from Facebook, Twitter, Flickr and YouTube. Agency.com was behind
the strategy, and in some respects, it was an immediate and enormous success, drawing huge numbers to the site and crashing Twitter in the process. Unfortunately, most of those people had something obscene or inane to say about the brand. The campaign was swiftly rethought, the Twitter element marginalised and, presumably, proper filters set up, but Skittles' social media experiment goes on.

Credit has to go to Skittles for finding a way to harness the conversation, rather than attempting to muscle in with broadcast-style messages.
"In social media, which is such a private place, brands can easily stand out like a salesman at
a dinner party," says Katy Howell, managing director of Immediate Future.

"After you have dished out whatever you are offering, everyone waits for you to leave so they can carry on their conversation. That's why, for brands, social media can be really dangerous,"
she adds.

Banner ads O2, Tesco and Vodafone

The unhappy spectre of ad misplacement came back to haunt the online fraternity in May, when O2, Tesco and Vodafone were among the brands whose ads appeared on Facebook beside groups supporting holocaust denial and the BNP. Facebook had accidentally embroiled itself in a similar controversy two years before, when the victims included the AA, eBay, First Direct and Vodafone; and in 2008, Orange, T-Mobile and Virgin Media found themselves booked onto ‘extreme fighting' sites in the US after a mix-up by an ad network.

The industry takes such slip-ups seriously, and so do brands. After the incident in May, Tesco promptly backed out of advertising around Facebook groups.

The IAB and its dedicated IASH offshoot are there to speak sternly to ad networks and sales houses where preventative systems are found to have failed. Most agree that IASH has had a transforming effect on the conduct of ad networks, which is why cases such as the above are relatively rare. "It has taken a while, but IASH is getting there, and if something goes wrong, ad networks know they will be booted out," says Jonas Jaanimagi, managing partner of WebAds.

Blogs Ryanair and Skype

No one is ever likely to be able to persuade the notoriously aggressive Ryanair that its ugly tiff with a blogger in February damaged its brand. There is an argument, indeed, that because Ryanair clearly prides itself on its cheapness rather than its niceness, the spat only reinforced the airline's punchy, no-nonsense reputation. But it features here because it would have been the death of any conventional brand, and because there is nothing terribly clever about being unpleasant.

The incident involved an unnamed Ryanair worker who visited the blog of one Jason Roe, who had noted an apparent bug in the airline's booking system. The representative's opening salvo - ‘Jason! You're an idiot and a liar!!' - set the tone for what followed, and Ryanair's official statement, when it came, took a similar line.

Robin Grant, managing director of We Are Social, wryly gives the airline credit for consistency of message. He points to an alternative approach his consultancy employed for Skype last October, when The New York Times wrote about the Chinese government bugging calls made by Skype users.

"It was a massive crisis for Skype," says Grant. He describes a recovery process that began with a frank, honest response from Skype president Josh Silverman within five hours of the story breaking, followed by a campaign to publicise the post among all the blogs and news sources that had picked up the thread.

"Within 24 hours of the crisis, Silverman's post was the number-one Google result for related searches," says Grant. "We had process in place to track conversations online, and Skype responded in a human way."

Brand advocacy Belkin International

In the US in January, a gadget blog exposed a Belkin International salesman for offering payment to consumers in exchange for positive reviews of its computer peripherals products on sites such as Amazon. An apology was forth-coming and the world kept on spinning, but with a little black mark against Belkin's name.

In the US, such incidents are considered to be ethical issues, albeit profound ones, but in Europe, they are positively illegal. A European consumer protection law enacted in 2008 effectively made it an offence for British and Continental brands to conduct covert operations online, so phony blogs, anonymous self-promotion and general misrepresentation all moved across the line into the realm of crime.

In the internet's Wild West days, not so long ago, such tactics abounded. It looked like they might have returned last autumn when blogger Patrick Altoft picked up on a scattering of blog comments, written as if by a variety of consumers, extolling the virtues of a Nokia phone. Some of them, he demonstrated, came from one IP address, but under three different names. No link with Nokia was ever demonstrated and the story cooled, but can we be sure this type of activity doesn't still go on, in subtler forms?

"There are companies and agencies breaking the law," says We Are Social's Grant. "But even if
it wasn't illegal, we would feel it was wrong, as it ought to be about open conversations."