After years behind bars, can prisoners re-enter a digital society?

tags in their spare time probably beats the alternative. But they’re only experiencing the theoretical digital world. The real one — the one with Facebook profiles, Spotify playlists, and unfettered web access – remains beyond their grasp.

“The vocational training they give here is from 30 years ago,” Butler says. “Nobody out there uses CD players anymore. Nobody sends letters. We’re the only ones doing that.” Steve Lacerda, another student in Code 7370, tells me that he used to work as a tech support manager, and that being cut off from the digital world while in prison has been harder than expected. “I come across problems, and researching them is tough,” he says. “I miss the Internet.”

For former inmates, the transition out of prison and into the 21st century can be jarring. Many newly paroled inmates, especially those who served long sentences, have never sent an e-mail, used a smartphone, or filled out an online form. The unfamiliarity of these systems can create hurdles when it comes to mundane tasks, such as buying groceries from the self-checkout aisle at the store or using an electronic subway pass. And when it comes to applying for jobs, small hurdles can turn into huge obstacles.

The post-prison lives of inmates are rarely easy, technology problems or no. 77 percent of ex-convicts are arrested again within a 5 year period of being released, according to a study conducted by the Bureau of Justice. But numerous studies have shown that vocational training and educational opportunities, like those offered by The Last Mile, can help keep ex-inmates from returning to prison. A 2010 study by The Rand Corporation showed that fewer than half of incarcerated people receive academic instruction while behind bars. Those who do receive educational or vocational training, though, are 43 percent less likely to become repeat offenders, and 28 percent more likely to land a job.

One graduate of The Last Mile, Kenyatta Leal, got his first smartphone shortly after being released from San Quentin, where he served the last part of a 19-year sentence for firearms possession. Leal, 46, was no stranger to technology – years before, he’d been given 40 days of isolation in “the hole” as punishment for having a cell phone in prison – but he’d never had a phone capable of downloading apps, streaming music, and sending e-mail. In his new job at RocketSpace, a San Francisco tech co-working space whose founder hired Leal after meeting him in Code 7370, he realized he would need to catch up.

“I didn’t have any tech skills, but I had bust-my-ass skills,” says Leal. “My boss gave me a Galaxy III on my first day, and I took it home, figured out YouTube, and watched, like, four different videos on how to send an e-mail.”

“Teaching men and women about computers gives them an opportunity to learn 21st-century job skills. Not just shoe repair.”

Eventually, Leal found other sites he’d heard about in prison, like Wikipedia, and learned how to download music on Spotify, keep track of projects on Evernote, and post photos on Instagram. Now, six months after his release, his time in the tech world has clearly rubbed off. On a recent evening, he was wearing a gray hoodie and jeans, and peppering his speech with tech truisms like “fail fast” while discussing his most recent gadget, an Android smartphone called the OnePlus One. Leal says that if prisons taught basic technical skills to inmates, the re-entry process would be easier.

“Prisons have an obligation to rehabilitate,” he says. “It’s called the California Department of Corrections and Rehabilitation. And teaching men and women about computers gives them an opportunity to learn 21st-century job skills. Not just shoe repair.”

Another recent California parolee, Troy Williams, who served 18 years for aggravated kidnapping, says he has been struggling to adapt to a new digital society. “I walked into this halfway house and there was this old phone booth in there, and I grabbed a quarter and tried to put it in the coin slot,” said Williams, recalling the days immediately after his release. “One of the guys behind me was laughing.” Williams asked the man if there was something funny. The man exclaimed, “that phone hasn’t worked in years!”

Williams is no tech neophyte. In 2007, he founded the San Quentin Prison Report, a one-man documentary TV show, which he filmed using some equipment left behind by a production team from Discovery Channel. The footage was shown on a closed-circuit station within San Quentin. He later started producing segments for 91.7 KALW, a local radio station in the Bay Area.

“I was able to do some pretty remarkable stuff for a prisoner inside of the walls,” says Williams. Now, though, Williams is faced with the challenge of finding a job on the outside. ”I’m really optimistic right now,” said Williams. “I feel like I can accomplish the things that I’ve waited 20 years to do.”

Most inmates will have trouble searching for jobs. (One study gathered by the CCA showed that only 12.5% of employers said they’d accept an application from someone with a criminal record.) But inmates who have been locked up for years, and have missed out on technological progress in the meantime, have an extra burden. Almost all of today’s entry-level service jobs require an applicant to fill out a web-based form, send a PDF résumé, or use an online scheduler. Many clerical functions require familiarity with Microsoft Office and other business programs. Paroled inmates who lack these skills are often stuck in limbo.

“If you look at the kinds of jobs folks are going to be applying for out of prison, more than 90 percent of them now, it’s all online submission,” says John Laub, a professor of criminology and criminal justice at the University of Maryland. “You can’t go to a restaurant and say, ‘Hire me as a dishwasher.’ It’s all online. And there’s basically no training about, how do you create a resume? How do you create a PDF? How do you upload a file?”​

“If you’ve been in prison for 11 years…there’s a whole world that you’re largely unaware of.”

In 2013, three researchers from Arizona State University found that “participation in criminal lifestyles contributes to digital inequality” by removing entire populations off the grid for years at a time. (The study, published in the Social Science Review was titled What the f#@% is a Facebook?’ to ‘Who doesn’t use Facebook?’: The role of criminal lifestyles in the adoption and use of the Internet.). Its authors concluded, “It seems reasonable to suggest that time spent behind bars ‘freezes’ individuals’ exposure to and familiarity with new technologies.”

Scott Decker, one of the authors of the study, put it more bluntly in a presentation at the National Institute of Justice in 2013. “If you’ve been in prison for 11 years,” he said, “not only have you missed Facebook, you missed email and downloading things from a website and Craigslist, and there’s a whole world that you’re largely unaware of.”

Some criminal justice researchers, like Bruce Western of Harvard’s Kennedy School, have proposed a national re-entry program for paroled felons that would include education on some basic technical skills. But no such program exists today, meaning that for most parolees, their first days outside prison walls are spent trying to teach themselves many years worth of technical skills.

“[Prisons] would be wise to adapt, sooner than later,” says Scott Nelson, a policy consultant with the Texas Criminal Justice Coalition and author of the criminal justice blog Grits for Breakfast. “As we get to an era where frankly, most criminals are younger people, folks are just glued to those phones for so many things.”

Manuel Colon Jr., a father of two who recently spent 27 months in Oakland’s North County Detention Center, is now back home and seeking employment. Colon says that when most former convicts he knows re-enter society, they get involved with organizations and programs; but sometimes that support isn’t enough.

“We’re human,” he says. “Everybody needs some help.”

While Colon was incarcerated, he took it upon himself to stay abreast with the latest advancements in technology. “I was learning about the Bitcoins and stuff,” he says, adding that he was an avid reader of Wired. Colon said there’s a difference between people who actively try to stay connected with the world while incarcerated, and those who don’t. “Certain people got this mentality that, ‘I’ll cross that bridge when I get to it,'” he says. “Which ain’t cool. Because you get to that bridge, and then it won’t be that easy to cross; you’ll be stuck. You’ll be lost.”

Leal, who has since been promoted to operations manager at RocketSpace, says that it’s only a matter of time before prisons start to incorporate tech skills into their programming. And he predicts that fearful prison officials will find ways to overcome the safety issues. “People understand that technology isn’t going away,” Leal says. “It’s embedded in everything we do.”

In San Quentin, the digital divide is still in place, even if it’s getting narrower these days. With no Internet access, no officially sanctioned smartphones or tablets with which to brush up their skills outside of class hours, and no willingness to jeopardize what little access they have by sneaking in contraband, the members of Code 7370 are stuck in an odd kind of limbo – close enough to the digital world to know its basic contours, but too far away to see it in clear focus.

“The real world is literally a couple of miles away – there’s a building here where you can look out the window and see the lights of Oakland,” Butler tells me, while trying to write code for an accordion menu on his test page. “I’d like to get on Facebook and Twitter and tell everyone, ‘Hey, I’m out of prison!’” He looks up from his screen. “I want this.”

Next, we look at one jail that is trying to become the “Google or Facebook of corrections.”