Ken Strutin
Ken Strutin ()

Technology is transforming our thinking and our communications. No longer bounded by speech and writing, we transact law in big data from virtual offices. Lawyers are surrounded by automation, but not the incarcerated. Theirs is the shadow play of confinement, the moldering of books, the magics of letter writing. An Information Curtain lies between the far-points of actual innocence and artificial intelligence, making access to the courts a technology issue.

Glaciers of Ink

We are on a journey from an ink drenched past to a paperless future. “Thinking like a lawyer” is being recast by algorithms and digitization. See Ken Strutin, “Automatic Justice: Shaping the Legal Mind of Tomorrow,” LLRX, June 2017. But there is always one precinct of society that never seems to change.

Attorneys work in a freewheeling technosphere, while paperbound prisoners are mired in glaciers of ink. And handwritten letters from inmates, vestiges of a waning paper culture, are hard put to penetrate a high-tech mindset.

A question of the day feature, posted by the American Bar Association Journal, asked for lawyers’ views on prisoner letters. See Jill Schachner Chanen, “How Do You Deal with Unsolicited Letters from Prisoners?,” ABA J., Aug. 29, 2012. One hopeful theme emerged: “Everyone deserves a response.”

Electronic messages tend to sanitize communications because they are easily created, readily dismissed, and quickly forgotten. All too often, the passion of words is dulled by the wrong information container. But when a note is tied to a rock, the rock does the talking.

Every day the incarcerated mail pleas for help: “I’m innocent.” “I don’t understand the law.” “I have been denied parole for the tenth time.” “I don’t want to die in prison.” Too often, the closest a prisoner comes to assistance is a stamp on an envelope addressed to a stranger.

Prisoner letters tell tales of wrongful conviction, excessive confinement and suffering created by the state’s blunt solutions to complex problems. Their pleas are reminders to all of us that within each of them is the spark of human dignity.

Still, the plight of the confined cannot be whittled down to 140 characters. Handwritten petitions are weighted with the pathologies of language and literacy, psychology and poverty, and outmoded print media. Theirs is a new burden, communicating at the pace of snails with a world that moves at roadrunner speeds.

Technology bends to the needs of its users. See Robert Ambrogi, “Debuting Tomorrow: A Keyboard Designed Just for Lawyers,” Law Sites, Jan. 4, 2017. But prisoners are technology free. So, their earnest pleas need a compassionate reading.

Above the Fold

To come from behind the Information Curtain, people denied technology must imagine how people with technology think. In other words, pencils and typewriters must learn the syntax of iPads and search engines.

A prisoner’s cell is a cobbler’s bench where hand hewn correspondence is multiplied thousands of times in the faint hope of a reply. See Larry McShane, “Inmate Goes Free After One of 62,000 Letters Pays Off,” Seattle Times, Aug. 26, 2001. If there is a chance of attracting attention, these letters have to be readable, their messaging economical.

Writing to someone in a paperless law office means that incoming letters might be scanned or digitized. Hence, prisoner correspondence must be smartly punctuated so that a machine, as well as a person, can read them. See Marc Davis, “Document-Scanning Firms Can Save Lawyers Money and Space,” ABA J., July 1, 2016.

Word processing and email have eliminated the back of the page, folded footnotes beneath mouseovers, and replaced paperclips with hyperlinks. Technology has made origami out of the traditional threefold paper letter.

When tweets and elevator pitches are the stages for persuasion, when countless texts and emails are exchanged daily, the information consumer is accustomed to reading above the fold. Thus, long handscripted correspondence can be a cognitive burden that wears down the tech savvy reader before their interest has been earned.

The lessons of lawyers writing to clients become equally valid for the incarcerated writing to lawyers—simplicity, succinctness, and clarity. See James W. Martin, “How to Write Letters Nonlawyers Will Read,” Practical Lawyer, Jan. 2000, at 19. For the letter recipient, an added measure of tolerance is necessary considering that prison issued pencils don’t come with spellcheck.

Compassionate Reading

For their part, lawyers receiving prisoner letters must realize that pro se literacy skills rollercoaster with speech and language, knowledge and learning, physical and mental status, sensory impairment and print disabilities, and most of all, conditions of confinement.

Often enough, the writings of the confined reveal legally valid causes, viz., innocent of their crime (actual innocence); innocent of their pleas and verdicts (wrongfully convicted); or innocent of their confinement (punished beyond rehabilitation and fairness). See Ilann M. Maazel, “How to Get Out of Jail (If You’re Innocent),” N.Y.L.J., Nov. 4, 2014, at 3. So it is that their mailings resound with injustice.

Prisoner letters are heartfelt holographics, the last testaments of vanishing people. For prison is the leaden decay of humanity; a postscript to life unlived. So, a generous portion of understanding and empathy is required by the readers.

Indeed, digital dictation, document assembly and OCR capture can automate replies with just a hint of humanity. See Phil Metcalf and Nerino J. Petro Jr., “A Guide to Speech-Recognition Software,” GP Solo (ABA), March/April 2014.


The raw correspondence of confinement can be vexing for overworked attorneys and government officials, but not so onerous as serving an unjust sentence or living in inhumane conditions. Imagine how far the incarcerated letter writer is from the free person, who with a computer and a keyboard access limitless communities of knowledge.

Dispatches from prison can humanize the punished, liberate their dignity, alchemize their readers, and when responded to, ennoble everyone. In the end, reading a handwritten plea for help from an incarcerated human being might be the last badge of humanity in a technological age.