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Microsoft investigators noticed there was an oddly similar pattern in a seemingly unrelated area, advertisements for the game World of Warcraft. Though investigators weren’t sure how the two were connected, they began to see some similarities. Although traffic appeared to come from different computers, it was actually coming from two proxy servers, which mask the original address of a click.

Microsoft began trying to stop the suspect traffic, but a little game evolved. Microsoft would block a server, or block a certain level of traffic for those advertisements, but whoever was on the other side of the clicks kept finding new ways around the company’s fixes.

“They’re basically just trying to figure out what our filters and technology tools are going to flag, and seeing if they can change their thresholds to get around it,” Mr. Cranton said. “Then we figure out what they’ve done and we change our thresholds, and it goes back and forth.”

Microsoft didn’t know why someone would be interested in both World of Warcraft and auto insurance ads, though, until a third party told investigators that an advertiser for World of Warcraft keywords named Eric Lam was also taking a fee for directing traffic to auto insurance sites. Investigators figured out that seven different accounts, registered under different individual and company names, were linked to Mr. Lam and two other defendants, Gordon Lam and Melanie Suen, believed to be Mr. Lam’s brother and mother.

Microsoft’s theory is that Mr. Lam was running or working for low-ranking sites that took potential client information for auto insurers. The complaint said that he directed traffic to competitors’ Web sites so they would pay for those clicks and exhaust their advertising budgets quickly, which let the lower-ranking sites that he sponsored move up in the paid-search results.

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When people clicked through to his site, it asked them to supply contact information, which he then resold to auto insurance companies, according to Microsoft’s complaint, which estimated his profit at $250,000. In the complaint, it also said it had to credit back $1.5 million to advertisers because of the Lams’ alleged fake clicks. Microsoft is seeking $750,000 in damages from the defendants.