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A Massachusetts man pleaded guilty to 25 federal crimes in connection with one of the most wide-ranging cyberstalker campaigns in recent memory.

Ryan S. Lin, 25, targeted his former roommate and a half-dozen other people with more than a hundred hoax bomb threats, stolen private diary entries and nude pictures, fake solicited rape fantasies online, and other tactics, according to federal authorities.

Lin was arrested in October, and pleaded guilty Wednesday to seven counts of cyberstalking, five counts of the distribution of child pornography, nine counts of making hoax bomb threats, three counts of computer fraud and abuse, and one additional of aggravated identity theft.

The plea will carry least seven years in prison, and a maximum of 17 ½ years, according to the U.S. Attorney’s Office for the District of Massachusetts.

The account of events outlined in federal charging documents shows an escalation in criminal behavior—and invasions of the victim’s most guarded secrets.

It began when Lin answered a Craiglist for a roommate in a Watertown, Mass. residence, in late April or early May of 2016. He joined three roommates, including the 24-year-old victim.

The victim had an Apple MacBook laptop kept in her bedroom. But there was no password on the computer—and no lock on her door.

In a single document on the laptop was the passwords to all of her online accounts, according to federal court documents.

Lin, a computer software expert who had a degree in computer science from Rensselaer Polytechnic Institute, started exhibiting strange behavior toward the woman soon after moving into the apartment, according to the affidavit in support of the original criminal complaint, filed by an FBI special agent on the case.

The victim moved out of the house within a month of Lin’s arrival.

But even before she left, his text messages referenced an abortion she had months earlier. It was something she had not shared with him or the roommates—but that she had written about in her private diary, stored on her Google Drive account.

Her prescription medications were flushed down the toilet, causing flooding and damage throughout the apartment.

After she moved out, she returned back to the apartment to retrieve some other belongings—and she found printed out copies of her online diary scattered around her former bedroom, according to the court documents.

Lin was forced out of the apartment in the summer of 2016.

But someone around that time sent parts of her sensitive diary, along with a sexually-explicit collage of her pictures, to family, friends and associates—even the car dealership from which she leased her car—from a “spoof” email account that was intended to appear to have come from her. The emails eventually reached her boss, her coworkers, her 13-year-old sister, her parents, former teachers and a series of institutions connected to the woman.

A masked account sent pornographic pictures of pre-pubescent girls to her mother, her former roommate and two of her former college classmates.

Sexual solicitations for “rape fantasies” and “gang bangs” were posted online—and resulted in three men showing up at the victim’s door seeking sex, as well, according to the documents.

Lin pleaded guilty to making more than 100 bomb threats in Waltham and the surrounding areas—including 24 in just one day. One hoax threat was a school shooting claim made last summer, according to the affidavit.

Lin repeatedly tried to keep in touch with the victim through social media, as well.

Lin used “The Onion Router,” or "TOR," to anonymize his IP address, and virtual private network, or VPN, devices for texting services. At his Waltham workplace computer, artifacts for PureVPN, Protonmail, TextNow and other surreptitious software were found on the machine, even though it had been reinstalled with a new operating system in the month since he had been fired in July 2017. All were used to mask his IP address—but shared email address sign-ins connected the devices, according to the FBI agent.

But it seems the victim in the latest case was just the latest of Lin’s targets, according to the affidavit filed in October 2017. Interviews with people Lin knew in high school and college indicated he had harassed others—even a roommate he had lived with in the months prior to arriving in Watertown.

“The investigation has revealed that Lin had previously engaged in a similar course of conduct with other acquaintances, including high school classmates, college classmates and roommates, and his roommate immediately prior to moving in with Smith,” the FBI special agent swore.

The sentencing is scheduled for Sept. 14.

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