When Paulo Demetrick, a 29-year-old federal prison inmate in Virginia, was asked, “If you could have a window in your cell, what place from your past would it look out to?,” his mind began to race. After 11 years behind bars for robbery, how could he think of just one photograph?

At first, he thought of his childhood, moments with friends and family. But it didn’t feel like enough. He sat in his cell for five days obsessing over the image. In the end, he chose a Bestway supermarket.

“At Bestway I learned to mingle with and learn from people of all walks of life,” he wrote in his request.

When Mr. Demetrick received the image, he was ecstatic. Apart from the store’s name changing from Bestway to Bestworld, the supermarket was exactly how he remembered it. “It has been over a decade and with the D.C. area having so many changes over the years I was glad this supermarket survived,” he said.

The image still hangs on the bulletin board next to his bed.

The photo — a reminder of what was and may still be — was done as part of “Windows From Prison,” a huge initiative that the cultural organizer Mark Strandquist started in 2012. He has posed the same question to hundreds of prisoners who had been convicted as juveniles in the Washington area but were later dispersed to federal prisons nationwide.

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It grew from “Write Home Soon,” a continuing project, which asks people to create postcards portraying a place they have lost. Mr. Strandquist thought incarcerated youth would be a good addition, so he reached out to Free Minds, a Washington-based nonprofit group that teaches incarcerated teenagers literature and creative writing. When he saw the work produced by the teenagers, he was inspired to propose an entirely new project to the executive directors of Free Minds.

Mr. Strandquist started to think about the power of words as a means to describe a scene. Then he began to think about his own background in documentary photography, a field he no longer practiced because he felt there was little reward for his subjects.

“From the beginning, it was incredibly important that the project strive to generate a new kind of prison photography,” he said.

There was also the issue of security limitations.

“I thought, if we can’t bring cameras into the prison, we have to ask people to respond to a prompt,” he said.

Since then, Mr. Strandquist’s project has brought thousands of inmates together with law clinics, universities and photographers across the country. In early versions of the project, all the images were photographed and mailed back. But the project has since expanded.

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This spring, he worked with students from the Duke Ellington School of the Arts in Washington. He would take students to each of the prisoners’ requested sites to sketch out the composition with digital cameras, then return to the classroom and decide on one image. The students returned to the site, this time with a medium-format film camera to shoot the final scene.

“Working that way slows down the process,” Mr. Strandquist said. “It’s not about the decisive moments.”

Last April, he printed the images alongside the inmates’ letters on 12×9-foot banners and set up a large installation in the public square at George Mason University in Fairfax, Va. He placed the banners around a central stage where for several days, debates, lectures and public sessions on prison reform and mass incarceration were held. Additionally, teenagers and adults from Free Minds currently in the re-entry process read poetry.

Mr. Strandquist hopes that by engaging the public, he can create a dialogue that helps shatter some common notions about prisoners and raise awareness about mass incarceration, a relevant issue because the United States has the world’s highest incarceration rate. With 2.2 million adults (or one in every 100 adults) in prison or jail, the United States accounts for just under a quarter of the entire world’s prisoners.

Brett Dignam is a clinical professor of law at Columbia University, where she is also the director of the Mass Incarceration Clinic.

“You don’t understand this problem until you are sitting opposite a table of a prisoner,” she said. “A lot of my students come in with preconceived notions of these horrible violent people, but they are brought up in different neighborhoods or they have different luck, but they are all the same age as my students.”

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Ms. Dignam said of Mr. Strandquist’s work, “To give them a pictorial representation of the outside world, to respond to a prisoner’s individual request, is really something huge.”

Kenneth Brewster — K.B. to those who know him — has been incarcerated since June 2005 for first-degree murder, and he will not be released from prison until 2062. “At least that’s what the paper reads,” said Mr. Brewster, 26. “Hope is highly addictive.”

Last year, he received the Windows From Prison query.

“It allowed my incarcerated mind to wander for a moment, to dig deep in the past and remember what’s now behind me,” he said. “It brought sadness, but gave me more joy to be able to remember and know how beautiful life can be.”

Mr. Brewster chose a view from his home on Oliver Street Northeast (Slide 9). He still remembers the day he received the photograph. “It was in a regular envelope, it wasn’t embellished with designs or enclosed in a package as if it were Christmas,” he said.

Initially he thought it was a notice about a coming event. Then he opened the envelope and saw the photo.

“People were walking around, the streets were littered with cars and … the sun was casted over the buildings,” he said. “I could tell that it was around 3:30 p.m. It was beautiful. I sat there staring at it for almost an hour dreaming and remembering when life was simple and carefree.”

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