A series of articles on how technology is changing prison as we know it.

Jim was three whiskeys in when someone plunked down a red leather handbag. He looked up, shielding his eyes from the afternoon sunlight. “I thought I’d find you here,” said a warm and officious voice. Jim blinked, focused on the face of Molly Moore in a peach silk pantsuit. He’d noticed it at the audition. She looked like a creamsicle. “You found me,” he said. He wasn’t in the mood to talk.

My favorite pecan pie recipe is from a Methodist cookbook sold at a church not far from the Virginia farm where my grandmother grew up. The pie’s perfectly gooey consistency comes from an obscene amount of Karo corn syrup; its slightly salty crust accentuates the toasty flavor of baked pecans. I make it every year for Thanksgiving, the quintessential American holiday I celebrate despite not living in the U.S. and not being American.

In a small conference room nestled inside a secure red-brick building, I met with 11 fellow staff members of the Nash News, a prison newspaper in North Carolina. It was late March, and we were huddled over folding tables to discuss a novel idea: hosting a mock election for Nash Correctional’s 900 medium-custody prisoners. Cris, the paper’s graphic designer, suggested it. “Maybe we can learn how our choices compare with society’s,” he said, smiling. “It’ll make a helluva story, too.”

The first thing I do in the morning is check PurpleAir. It shows dozens of dark maroon dots around the southern Oregon valley where I live, and this is bad. During the night the air quality has chromatically shifted from an “unhealthy” red to a “very unhealthy” maroon. Begrudgingly, I pad pajama-clad to the windows, where I peel back the curtains and stare directly into the dull orange face of a sullen, smoke-soaked sun. Coffee seems so pointless.

When my partner got me a sleep tracking ring for my birthday, I was ambivalent. I’d long resisted the siren song of the quantified, optimized self, and I was cynical about trading privacy and personal data for personalized insights. After a decade working at Bay Area startups, I knew too well that technologies are rarely inert tools. They shape our desires and behavior. They demand things of us—too much, sometimes. At the same time, I needed to do something about my sleep. Even before I becam...

The 36-year-old vlogger appeared on my screen wearing a curly black wig with a big yellow bow, fake oversize glasses, and a green dress. Caricaturizing a homemaker, her signature over-the-top costume transformed Leslie Ann Pamela Montenegro del Real into her online persona: a satirical YouTuber best known as Nana Pelucas. From 2012 to 2018, Montenegro del Real and her husband ran an online outlet called El Sillón magazine from Mexico’s popular beachside city of Acapulco.

It’s 7 p.m. at Central Prison in North Carolina, and I find myself in a familiar dilemma. I’m nearing the end of my last bundle of the prepaid minutes I use to send messages, which I bought from the private company ViaPath on the promise of communicating with the outside world at a rate of 1 cent a minute. I could purchase another bundle—but I’d be left without money for toothpaste or deodorant.

When Sgt. 1st Class William Reinier logs in to Reddit at work, he’s not doing it to kill time or slack off. As a public affairs officer responsible for social media outreach for one of the Army’s most senior service members, Reinier scans the site as part of his official duties. He’s looking for posts about some of the most pressing problems facing the Pentagon: suicide rates, sexual assault, and horrible living conditions at multiple installations. Users often tag him to get his attention.

The writing sounded like the typical 3 a.m. word-vomit of course concepts—the sentences relaying a superficial understanding at best of what we had done this semester and the argument only vaguely responsive to the prompt. It was the sort of paper that usually makes me wonder: Did this student even come to class? Did I communicate anything of any value to them at all? Except there were no obvious tells that this was the product of an all-nighter: no grammar errors, misspellings, or departures into the extraneous examples that seem profound to students late at night but definitely sound like the product of a bong hit in the light of day. Perhaps, just before the end of the semester, I was seeing my very first student essay written by ChatGPT?

The first time I visited death row as an investigative intern, the man whose case I was working sat behind a plastic divider and ran his fingers through his graying hair. He picked up the phone at the same time as his attorney, sitting beside me, lifted the phone on our side of the divider. “I recognize you,” he said to her, with no hello. “But you might be somebody else.”

I’ll never forget the way my body felt after that blast inside a dugout trench in northern Iraq. It was 2016, and I was there as my unit’s journalist, accompanying Sgt. Joshua James and the seven other men in his team. Each time James and his section fired their artillery piece—a long-range cannon that could shoot high-explosive rounds for miles—the force of the explosion was so strong it knocked the breath out of me and caused a shudder in my bones. As the dust cloud began to form from the sand blown off the walls and ground, filling our noses and staining our uniforms, I also felt a dull pain in my head, like I had just gotten hit in the face.

When my dad died, he became part of the cloud. Not the one up high in the sky, but rather an online cumulus that now stores and archives a record of his last 18 months on earth. On my laptop, and even more prominently on my phone, I carry with me digital traces of my dad that I can’t yet bring myself to access. Four years after his death, I still sit with a kind of grief that remains more raw than residual, and his memory lingers in digital purgatory—undeleted yet untouched; saved but not sought. He “lives” in this liminal digital space; like a grave I can’t yet bring myself to visit, but simply know is there.