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Former prisoners struggle to re-enter society. What happens when society moves online?

Many of the social services and job programs that former prisoners rely on to achieve re-entry into their communities are inaccessible without a comprehensive knowledge of the internet.
After spending decades in prison, Renaldo Hudson had to learn how to use a smartphone.
After spending decades in prison, Renaldo Hudson had to learn how to use a smartphone.Alex Wroblewski / for NBC News

When Renaldo Hudson left the Danville Correctional Center on Sept. 2, he was beaming. As the sun shone down on a hot day in Eastern Illinois, Hudson took his first free steps in 37 years. 

Later that day, he arrived at the Precious Blood Ministry of Reconciliation, a restorative justice nonprofit that helps former prisoners get on their feet. There, he saw friends for the first time in years and hugged his attorney, Jennifer Soble.

He was also handed a Samsung smartphone, a piece of technology that wouldn't have been imaginable to an American in 1983.

"People would say things like they were so simple." said Hudson, 57. "'Listen, go to your browser and open this up.' I'm like, 'Who is the browser?'" 

Hudson, like many people who leave prison after lengthy sentences, quickly realized he had entered a new world, one dependent on technology and innovation. The challenge he faced has been amplified in the past year as the Covid-19 pandemic has driven many more parts of life online.

Many of the social services and job programs that former prisoners rely on to successfully re-enter their communities are inaccessible without a comprehensive knowledge of the internet. Advocates say that's an issue that can be overlooked by organizations meant to help, and former inmates sometimes struggle to adapt to decades of technological innovations that passed them by while they served time.

Renaldo Hudson uses Zoom.
Renaldo Hudson uses Zoom.Alex Wroblewski / for NBC News

In 1983, when Hudson was imprisoned, cellular phones weighed about 2 pounds and were larger than bricks. An early version of the internet is considered to have been born that year, although it looked nothing like the internet we know today. 

"It connected me to the world on a level that I couldn't have imagined," he said. 

There are essential services many prisoners returning home need access to immediately, like health insurance, food stamps, medical care, job opportunities and state-issued identification. Before the pandemic, people could physically go to the Department of Motor Vehicles, a social services office or a staffing agency. Now, everything is online, and the obstacles in the way of gaining access to those services are far greater.

Bringing people up to speed can be challenging.

"A person will come home and we'll have to, like, really, really take the time to really show them how to navigate around everything," said Wendell Robinson, a program manager at Restore Justice, an Illinois nonprofit focused on criminal justice reform and lengthy sentencing relief, who came home in 2018 after 25 years in prison. "If it's sending emails and attaching documents, everything, just all the preliminary steps of navigating through this fast-paced world."

Soble, who is also the executive director of the Illinois Prison Project, said that most of her group’s clients are in their 60s and 70s and that most of them have been in prison for 30 years or more.

“They literally do not know where to begin,” she said. “They don't know how to turn the computer on when they first come home."

Learning from the ground up

Maria Burnett, a Washington, D.C.-based human rights lawyer, didn't even consider gaps in digital literacy when she began taking on pro bono compassionate release cases during the pandemic. 

At least 18 states and Washington implemented some form of compassionate release last year to lessen the density of prisons, releasing prisoners close to the ends of their sentences and releasing elderly and medically vulnerable prisoners at greater risk of contracting Covid-19.

Under Washington’s compassionate release guidelines, Burnett had to draft a detailed re-entry plan for her client, John, who asked to be identified only by his first name. 

"I thought I had thought about a lot of factors and had been really meticulous in thinking through the challenges he would face," Burnett said. "I didn't realize how dependent all of those factors would be on his digital literacy."

Burnett didn't realize John was struggling to use technology until he began to miss online appointments. 

She was looking forward to hearing about John's telemedicine appointments but realized he didn't know that his phone had to be connected to Wi-Fi or cellular service to call in. Similarly, Burnett was eager for John to attend re-entry support groups on Zoom but realized he didn't know what a hyperlink was and therefore didn't know he could arrive in a Zoom room just by clicking on a line of blue text. 

"The prison system, I promise you, is really like walking into a time warp," Hudson said.

Harold Hagerman, a member of the Future Leaders Apprenticeship Program, which Robinson runs at Restore Justice, said he came home in April after serving a sentence of over 28 years in Illinois.

"A friend of mine, the very same night I came home, they gave me the iPhone 11, and I had no idea what the heck to do with that thing," Hagerman said. "I came home and it's like you've been in the stone ages when you see all this technology."

Harold Hagerman and Wendell Robinson.
Harold Hagerman and Wendell Robinson. Alex Wroblewski / for NBC News

Another problem among former inmates learning to use contemporary technology is not knowing the basics and being too nervous to ask for help. 

"The thing that becomes intimidating about that is you get to a point where you don't want to keep asking because you don't want to seem this slow," Hagerman added. "Like, OK, they showed it to me one time and they expect you to just get it."

Seeking help from the youngest generation

Beyond seeking help from nonprofit organizations and public libraries, former prisoners have learned the basics about technology from their youngest family members and friends.

Robinson said he met his 2-year-old nephew when he came home and was inspired by his command of the technology.

"This little guy, he walked around, he had a pacifier in his mouth and he had a pamper on, but he picked up the phone and used it like nobody's business," Robinson said. "That was more inspiration to me, like, I'll be damned. This little dude can't even read. He ain't even talking. He ain't even putting together full sentences. How is he going to outdo me?"

Robinson found that the youngest members of his family were not just the most technologically savvy, but also some of the biggest supporters on his technology journey.

"My nieces and nephews, the little bitty kids, were like some of the best teachers when they came to helping me in, you know, those initial steps," he said.

Burnett said her client learned to use Zoom from her 9-year-old daughter. They spent an afternoon sitting outside an internet-equipped cafe until he understood how the program worked.

"It was cool to see my daughter be so reassuring and so capable of teaching someone something with such grace," Burnett said.