Webware

This post has been corrected from the original. See fifth paragraph.

Short URL powerhouse Bitly is baking into its Web service the Yfrog picture-sharing service made by Imageshack. Yfrog competes with other Twitter-friendly image-sharing services such as Twitpic.

For users who want to create easy short links to images they upload from their computers, this will be a bit of a time-saver. Also, users will get the real-time click through data from their images on the Bitly site.

Imageshack CEO Jack Levin says that his 11-person company services 3 billion images a day. That's the highest hit-per-employee ratio in Silicon Valley, he boasts. He also says that Imageshack has, due to its tenure, a larger and more stable infrastructure than competitors.

I find it interesting that a service that I thought treated all sites equally--I'm talking about Bitly here--would make a deal clearly favoring a particular source. Of course, Twitter itself gave Bitly its big break when it baked the URL shortener into Twitter itself, replacing TinyURL. Benevolence, or favoritism, depending on how you look at it, flows downhill.

Levin agrees that deals like this are "Web politics" but is happy to have what is for now unique placement on the Bitly service. This post has been corrected from the original, in which it was stated that the Yfrog arrangement was an exclusive deal. Bitly CEO John Borthwick sent in this correction: "If users like it, other photo sites will be included."

The image-upload feature should go live on the Bitly page at the end of the month.

Bitly also announced on its blog that Google Reader and Typepad now generate Bitly links natively.

Previously: As the URL burns: The short-link soap opera.

Disclosure: Bitly and CBS, CNET's parent company, have partnered to create branded short links for CBS News. CNET itself has no partnership with Bitly.

Eric Woodward, creator of the short URL service Tr.im, painted his product into a corner when he announced first, that he was going to take it offline, and then a few days later that he wasn't. Nobody wants to trust their Web links to a capricious business that could go offline again, and take working links and traffic with it.

On August 17, Woodward put a fresh coat on the prior week's drama with a new gambit: He said he was giving the service to the community. In the bitter post announcing this plan, he continued to claim that due to the fact that Twitter made Bit.ly the default URL shortener for the service, a product like Tr.im has no real chance for success. Related, he says, is the recent announcement of the 301works archive for short URLs, which he sees as a craven publicity stunt to boost Bit.ly, since the same people behind it are also running 301works.

Woodward says that the Internet needs an open link-shortening service, because the traffic data short URLs generates is too valuable to entrust to a single company. "You can't get the aggregate data on what's being shared in real time by everyone," he told me. "Twitter wants to become a real-time search engine, so the data Bit.ly is capturing is very valuable."

(Bit.ly data is currently wide open, at least on an individual URL basis. Simply append "+" to a Bit.ly link to get traffic stats on it. Woodward wants to see a "fire hose" of short URL data, however.)

A Twitter keiretsu?
Woodward does have reason to be envious and even suspicious of the Bit.ly-Twitter relationship, although it's difficult to draw the connection all the way to malfeasance on the part of the two companies. And it's hard to believe that his strident posturing will win him much support outside of a small group of the most zealous open-source boosters.

Several powerful companies in the Twitter ecosystem are inter-related. Bit.ly's CEO is John Borthwick, and Borthwick is also CEO of Betaworks. Betaworks helps build companies in the social-messaging space. It incubated Summize, the Twitter search engine Twitter acquired last year, and through that deal Betaworks remains connected to Twitter. Betaworks has also worked with Tweetdeck -- which also uses Bit.ly as the default link shortener. The company has several other Twitter (and Facebook) projects running right now. Suffice it to say that if you're in Betaworks' network, you've got great access to Twitter. If you're competing with a Betaworks portfolio company to get Twitter's attention, you've got a tough road ahead.

Betaworks is one of the drivers of the 301works short URL data project, and it's the relationship between Bit.ly and 301works that led Woodward to shun the project, at least for now. "There's nothing wrong with it in theory, but it doesn't solve the link rot problem," Woodward said. He added, "Why would I give them the publicity?"

With so many URL shortening services out there, this was bound to happen to at least one of them: Trim is shutting down. According to a blog post by parent company Nambu Networks, it was an expensive and fruitless effort.

"We simply cannot find a way to justify continuing to work on it, or pay its network costs, which are not inconsequential," the post read.

Those expenses may have been particularly encumbering recently, when the service, found at Tr.im, was hit by a denial-of-service attack last week that knocked it offline.

The blog post was tinged with more than a hint of bitterness. Twitter, the service that led to the explosion of URL shorteners as Web users needed to truncate lengthy addresses to fit into a 140-character space, has shown a clear preference for Trim rival Bitly. Twitter uses Bitly as its default URL shortener, and it's even been rumored that Twitter may acquire it altogether.

"Twitter has all but sapped us of any last energy to double down and develop Tr.im further," the post read. "What is the point? With Bit.ly the Twitter default, and with us having no inside connection to Twitter, Tr.im will lose over (in) the long run no matter how good it may or may not be at this moment, or in the future."

What the company hasn't said: what will happen to existing Trim URLs? It's likely that Nambu Networks hasn't yet decided. If Trim is completely closed, that would mean that those shortened URLs would turn into broken links. It'd be possible to close it to new entries but keep existing ones, except that wouldn't solve the financial problem.

One commenter on the Trim blog post suggested that perhaps the service could live on in the form of an open-source project. But for now, its fate remains up in the air.

Twitter's dramatic rise has helped ignite an industry to shorten Web addresses to fit within 140-character messages. With the technology, though, comes a new handful of challenges.

Among the challenges are reliably connecting people to the Web sites they want to reach, keeping spam and phishing attacks at bay, and maintaining the service into the future.

Joshua Schacter, founder of Yahoo's Delicious site for storing and sharing Web bookmarks and now a Google programmer, summarized the issues in an April rant about short-URL problems. "I feel that shorteners are bad for the ecosystem as a whole," he concluded.

TinyURL's interface for creating short Web addresses.

(Credit: Screenshot by Stephen Shankland/CNET)

Until a remote future arrives when Twitter and the telecommunications industry decide 140-character messages are too short, though, URL-shortening services aren't going to go away. Fortunately, their potential problems can mitigated through careful use, and newer services such as Bit.ly are being designed expressly to avoid the pitfalls.

And even if some service falls by the wayside and stops functioning--well, welcome to the real world, where not all information is preserved.

"In the digital age, everything has a certain amount of bitrot," said Paul V. Mockapetris, who invented the Domain Name System (DNS) that serves as the Internet's address book.

Growing like weeds
URL-shortening services are abundant and becoming more so. They're usually designed with a priority on minimum character length, not easy reading: Is.gd, Bit.ly, Twurl.nl, Tr.im, Sn.im", Cligs, and TinyURL. If you want to see dozens more, Mashable has a long list.

And the traffic they handle is large. On a typical day right now, Bit.ly is used to create 5 million to 7 million shortened URLs each day, and it handles 25 million requests to expand them--and the growth rate is at a breakneck 5 percent to 15 percent week over week, the company said. Snipurl has delivered 53 billion since its inception. And TinyURL has a database of 293 million URLs.

URL-shortening services have been around for years--TinyURL was founded in 2002, and SnipURL, which also operates Sn.im and Snurl, in 2001. The services typically were used to keep long URLs from being split into chunks in e-mail, where line limits of 80 or fewer characters could break up a Web addresses.

So what's new now? First, Twitter, and second, shortening URLs is becoming an actual business--notably at present through the addition of "analytics" features that can let those who use the service see data about how many people clicked on links, when, where they're located, and the Web page where they found the shortened link.

TinyURL's funding today primarily comes from advertising on its Web page, but that's changing, said founder Kevin Gilbertson. "I'm working on something else that should increase that (revenue) quite a bit," Gilbertson said. He declined to share details at this stage beyond saying, "It will not change any functionality."

He's employed contractors, but with the new funding, he expects to hire full-time programmers and improve his computing infrastructure. Also coming is analytics. "We will be offering that sometime here soon," Gilbertson said.

Snipurl has been run as "a personal endeavor," said leader Shashank Tripathi, with just three employees, but the new climate has got him thinking about venture financing.

Getting analytical
Analytics are important for URL shorteners, in part because it helps the services break out of low-value freebie use to corporate accounts that need to track what's going on.

Bit.ly can tell you how many people clicked your short URL, where they clicked it, and which country they live in.

(Credit: Screenshot by Stephen Shankland/CNET)

"We have a bunch of commerce providers who have embedded Bit.ly into their systems. They're using it for tracking and understanding ROI (return on investment) on various promotions," said John Borthwick, Betaworks CEO and a Bit.ly investor.

Bit.ly is just shy of a year old. So why get started now when there already are dozens of alternatives? In short, to do it better, Borthwick said.

"At Betaworks, we had a series of companies who said there's a need for an URL shortener that was more scalable and reliable than the stuff out there today, that had real-time metrics associated with it, and that had an open API (application programming interface) so people could encode and read decodes through the API," he said. "So we said that's a problem we think we can solve."

The API lets third-party software such as TweetDeck or Twhirl call upon Bit.ly's servers to create a short URL. It also can be used to more easily show the destination URL hidden away behind the short URL.

URL shorteners also can give insight into hot trends by spotting sites people are sharing moment by moment. Bit.ly Now spotlights Bit.ly's top Web addresses hourly.

Grappling with reliability
Then there's the problem of reliability. URL shorteners add a new step to the process of retrieving a Web page, and when the service goes down, Web pages can become inaccessible.

"We've had some growing pains and some issues," such as a database replication issue in March and a faulty switch in April, said TinyURL's Gilbertson. And Snipurl's Tripathi said traffic spikes such as those from Michael Jackson's death can be tough to accommodate.

Compare that to DNS, an arrangement of impressive scale that converts a typed address, such as "slashdot.org," into the numerical Internet Protocol address that's actually houses the address, 216.34.181.48. There are primary "root" servers for DNS, but countless servers on the Internet mirror the primary address book or portions of it, providing broad protection against failure.

DNS is used not only every time a person visits a Web page--several times per page in many cases--but also each time an e-mail is delivered. And while it's had issues, it's generally been highly reliable.

The shortener companies are working on greater reliability for their services. And in fairness, their scale of operation, while growing, is vastly smaller than the DNS.

Still, there's a longevity issue. Shurl.net and URLtea.com no longer function, for example. It's easier to start a shortening service than it is to maintain it for perpetuity.

"Many knockoffs have come and vamoosed," Tripathi said, but he expects Snipurl to do better. "Unlike recent post-Twitter entrants into the space, our links have been around since 2001. While we cannot guarantee anything, we can tangibly claim to have been the best in terms of longevity."

Even without shortening services, URLs aren't guaranteed to last forever. Some "linkrot" is inevitable as companies come and go, services such as Geocities are closed, Net addresses are sold, and people decide not to pay the annual fee to maintain their domains. Here, Bit.ly can actually help by maintaining its own copy of the page.

Can you trust that link?
One of the problems with short URLs is knowing what you're getting into when you click them. Is that link really the fun video of the guy tripping into the lake, or is it site that will spam you or attempt to install malware? Is it really a warning from your bank about a bad transaction, or is it a phishing attack to try to fool you into parting with your password?

Clicking many regular URLs involves a leap of faith, to be sure, but not being able to see a "youtube.com" or "bankofamerica.com" name because it's masked by a short URL makes that leap even longer.

TweetDeck has a preferences option to show details of shortened URLs before you open them.

(Credit: Screenshot by Stephen Shankland/CNET)

"My thinking is that the No. 1 concern is the masking of dodgy domain names from user inspection, for example, those registered in .cn for seemingly English-language sites," said Vern Paxson, a University of California-Berkeley associate professor of computer sciences who focuses on Internet security.

Some services don't do much to help the situation. "Add adverts to your URL to get FREE Traffic," promises the LongURL.net site. "When you send this link to newsgroups, forums, Twitter, Facebook and other social networks, people will load source Web page with your own ad."

And SNVC asks, "Are you an affiliate marketer looking to cloak your affiliate links?...If you choose to check the 'Hide Real URL?' box then it will allow you to keep your shortened URL in the address bar by using a hidden-frame trick."

But avoiding the issues of opaque links is top of mind for many services. For example, adding the word "preview" in front of a TinyURL link will show a Web page with the destination URL expanded. Greasemonkey scripts and extensions let some browsers automatically show the expanded link. And Bit.ly's API permits the Tweetdeck application to automatically show the ultimate destination.

Many services also try to screen out nefarious Web pages through use of blacklists such as SpamCop or Google's Google Safe Browsing. There's brand value in being seen as a shortening service that can be trusted.

"With our brand, we're trying to create a relationship with our users where it's understood we're looking out for them," said Andrew Cohen, a member of Bit.ly's still-small team.

Clicking links from your friends involves trust--they're your friends, after all. But as Twitter becomes evolves into a global conversation, with tweets revealed through search and hashtag identifiers, short URLs from strangers become more common. The more companies use URL shorteners for analytics purposes, the more people will encounter those links outside of Twitter, too.

Fundamentally, URL shorteners are just the latest iteration an old problem.

"The trust issue...is not fundamentally different from other Web, email, and link techniques that are out there," said UC Berkeley professor Randy Katz. "It all comes down to context and being sufficiently aware not to blindly open anything suggested to you."

Last.fm announced Friday that it has launched a mobile version of its social radio platform for Google Android-based phones. The Last.fm app, which is already available for the iPhone and iPod Touch, allows users to listen to the company's streaming radio stations and plays in the background while users perform other functions on the device. Last.fm's Android app is free and available now in the Android Market.

URL shortening service, Bit.ly, announced Thursday that it has updated its Twitter plug-in for Firefox. The update now provides users with the context of a Twitter conversation when they hover their mouse over the "in reply to" link in Twitter. The update is available now for Firefox users.

Tripwolf, a travel guide site that combines professional material and user submissions, announced that it has closed a $2.5 million funding round led by the MairDumont Group. According to the company's executives, they plan to use the funding to launch an iPhone app and expand their operation abroad.

Vudu, a company that provides streaming movies through its set-top box, has launched an iPhone app that will allow its users to browse and search the company's catalog of titles, as well as purchase and rent those movies for viewing on their Vudu box at home. The app is free and available now in the iTunes App Store.

Dogpile has raised $250,000 in just two months for pets in need, the metasearch engine announced Friday. Its goal is to raise $1 million by the end of 2009. Dogpile raises the money each time a user conducts a search. The more searches conducted on the site, the more Dogpile can contribute to the American Society for the Prevention of Cruelty to Animals (ASPCA), as well as other animal-related charities. The Dogpile "Search and Rescue" program will continue through the end of 2009.

Disclosure: Last.fm is a part of CBS Interactive, which also publishes CNET News.