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Lyn Ulbricht moved to Colorado last year. She uprooted her life to be near her son, Ross Ulbricht, who is an inmate in a federal maximum security prison an hour outside of Colorado Springs.

Ross is serving two concurrent life sentences for his role in the founding and running of Silk Road, a dark web bazaar where users could buy and sell drugs and other illicit items, often using bitcoin. The charges against him included money laundering, computer hacking, and conspiracy to traffic narcotics. In a separate indictment, he was charged with procuring murder. Though that charge was dropped, Judge Katherine Forrest of the Southern District of New York cited it as central to her decision to go well beyond the minimum sentence of 10 years and instead imprison him for life without parole.

At his sentencing, Ross made a modest request: "I've had my youth, and I know you must take away my middle years, but please leave me my old age.…Please leave a small light at the end of the tunnel." Although Forrest was not moved, the Ulbrichts hope the Supreme Court may feel differently. If their case is accepted, it could trigger a landmark decision about digital privacy and autonomy, as well as about what responsibility the creators of online tools bear for what others do with them. Reason's Katherine Mangu-Ward spoke with Lyn by phone in April, shortly after she got a small piece of encouraging news from the high court about Ross' appeal.

Reason: Since Ross' conviction, there have been quite a few revelations about prosecutorial misconduct and other questionable practices related to his case. Can you describe what has happened?

Lyn Ulbricht: Even pretrial, there were so many issues. For example, the government deprived Ross of bail, based partially on allegations of murder for hire, then two months later dropped those charges. And those charges were never brought to trial. He was never tried or convicted for those charges, and yet Judge Forrest used those charges to enhance a very unreasonable sentence for all nonviolent charges.

That is one of the questions that [we're bringing to the Supreme] Court: Is it constitutional for a judge to use uncharged, unproven allegations to enhance an unreasonable sentence? That deprives Ross of his jury trial rights.

By the way, there is still an indictment [on the murder-for-hire allegation] in Maryland. It's been languishing there for almost five years, unprosecuted, based on evidence supplied by Carl Mark Force, a corrupt [Drug Enforcement Administration] agent who's now in prison.

That was another one of the things that was a huge issue: The existence of this corrupt agent was precluded from trial. The jury was not allowed to know about him or another corrupt agent who was working for the [National Security Agency] and the Secret Service at the time, Shaun Bridges. The defense didn't even know about his existence until after trial.

So this was not allowed to be known to the jury. And it seems to me that that could have easily led to casting a reasonable doubt on Ross' guilt. These people not only stole over a million dollars [from Silk Road] using their access as investigators, but they had the ability to act as Dread Pirate Roberts, the pseudonym of whoever was running the site. They could change passwords, PIN numbers, keys, write things in chats—change evidence, essentially. And this was not permitted to be known to the jury.

Our readers' ears might perk up when they hear that there was an NSA component of this, since it's not really about national security.

That part was brought up by the defense before trial, and the government never denied it. They simply mocked the defense. [The DEA's Force] said, "Oh, he's bringing up this crazy stuff about the NSA." This was around the FBI investigator Christopher Tarbell's testimony under oath about how he found the Silk Road server, which experts worldwide basically called a lie. It was gibberish, according to them. In fact, [cybersecurity expert] Robert Graham even said, "We think it was the NSA."

And this is all illegal. I think your readers probably know that, but the NSA investigating and using spying surveillance against U.S. citizens is illegal. When [Reason's] Nick Gillespie interviewed [NSA whistleblower] Edward Snowden at Liberty Forum, he asked about Ross: "Can we assume that the NSA was involved?" And Snowden simply said, "Yes," and later said it was unthinkable they weren't.

Well, a few weeks ago it came out that there are classified documents from Edward Snowden showing that the NSA was tracking bitcoin users urgently. Not terrorists, mind you. Bitcoin users. And since they were illegally targeting bitcoin users, there are a lot of questions as to the validity of the investigation [against Ross] at all.

This is very, very troubling, because of course it brings up the whole question of parallel construction and what many call "intelligence laundering," where the NSA uses their extensive surveillance abilities and invasion of Americans' privacy to go after people, basically, and then turns it over to the DEA, the [Department of Justice], and the [Internal Revenue Service]. This is a real slippery slope, in my opinion, to horrible Fourth Amendment violations. And it's something that everyone should be concerned about. We're turning into a surveillance state. I don't think most people want that.

What happened today with the Supreme Court?

Ross and his legal team have petitioned the Supreme Court on two very broad-reaching questions that affect a lot of people. They submitted that petition in December. And then in January, 21 groups, including Reason Foundation, joined in support of that petition in five amicus briefs. These are groups from both sides of the political spectrum. I think that's important to note.

We just went through the process where a batch of cases are brought into conference to evaluate whether or not the [justices] were going to take the case. If they reject it, that's very, very bad. If they are willing to take it, that's very, very good. That was on Friday, so it was kind of a nail-biter over the weekend. And on Monday we found out that at least they did not reject it. There was a list of over 200 cases they did reject, and we combed that list and Ross was not on there.

It could have been relisted—just kicked down the road to the next week. But we found out today that it was not on the list for relisting, either, which indicates very strongly that they are probably holding it, pending another important Fourth Amendment case, Carpenter v. U.S. [which was argued last November]. So we're happy about it. We're still in the game. Ross' case is still before the courts.

What is Ross' life like right now? I know that you visit and correspond with him frequently.

Ross has been put in a maximum security prison, which is where the Bureau of Prisons puts its most violent offenders. He's a totally peaceful guy, but he's there because they automatically put people with a life sentence in these places, whether [their crimes are] violent or not.

Ross has no record of violence. He's a first-time offender. And actually, just as an aside, I've had guards come up to me, my husband, Ross, his lawyer—not only guards, but his counselor, his case manager—and they have all said, "Ross doesn't belong in here. What's he doing in here?" It's really a dangerous place. It's full of violent people, violent gangs, and there were a couple of stabbings just last week.

"I want to provide to him a lifeline to the outside world, so that [the prison is] not his only reality. That's what happens to people, and then when they get out, they can't assimilate well. It's a terrible system."

Is there anything that could get him moved?

Eventually I think that you prove yourself, which of course Ross will. They love him there. He could be moved to a medium security [prison]. But that's years away. And there are violent people there, too, of course.

What is his daily schedule like? How much contact does he have with the other prisoners?

Under normal circumstances, he's in a unit and he knows a lot of the people in the unit. But a lot of times they're having lockdowns lately. That leaves him locked in his cell for days at a time. It's been, off and on, at least half the time since Thanksgiving. When he's in a normal situation, he can walk a track and look at the mountains and be outside, which is really important for Ross because he's very outdoorsy and loves nature. He can go to the law library. There's a chapel where he can go meditate or pray. They have controlled moves—they can't just wander around, but when a move comes, it's announced, and then they can move to the next thing.

He has friends. His birthday was this past month. He turned 34 in there—his fifth birthday in a cage. Some of the guys got together and paid somebody to draw a nice card for him and then put together a meal for his birthday. It was really sweet. He's had no real issues or conflict. He's well-liked, which has been true for his whole life. It applies in prison too, you know? They're people.

As someone who's in there for a different reason than many of the others, do his fellow inmates find him a curiosity?

They know everything about everybody in there. They're well aware of Ross' notoriety, and they know he's a peaceful guy. Actually, there are other nonviolent people. A good friend of his, Tony, is doing a life sentence for marijuana. He's already served 13 years, and the federal prison happens to be in Colorado, where it's legal. That's insane, OK?

There's another good friend of his, Jose, who is in there because of the three-strikes law—thank you, Bill Clinton. One of his three strikes was residual cocaine on a dollar bill years ago, and he's got a life sentence. Ross says he's such a sweet person. Not everyone in there is dangerous or violent. The guy he shares his cell with isn't, luckily. But that said, there are gangs.

[The other inmates] know who Ross is. He passes Reason around, and they ask him about bitcoin—they think he's the expert about things like that.

What kind of person would you have expected to find in a maximum security prison before this happened, and what do you think about the people who are his friends now?

Sometimes I say, "Ross, I worked all your life for you to have a good peer group and good influences, and now you're friends with gang leaders." He's like, "Mom, gang leaders are people too." That's his thing. And he said he hasn't met one person who's truly evil in there. He said, look, some people made very bad decisions, but a lot of it has to do with the drug war. Of course there are some people you probably wouldn't want to live next door to. I'm not for everyone getting out of prison. But we have the technology to put ankle bracelets on people, let them go home to their families and their children. I think we should do a lot more of that.

What's your best-case scenario, going forward?

I'd like to get to the point where Ross could have a new trial, a fair trial, one that brought everything forward and he would be exonerated and free. That's our goal, for Ross to be able to come out and have a life. The thing is, you'd love Ross. He's not going to be somebody who's a threat in any way, and I know that he would never even come close to crossing the line into breaking the law again. He's not that stupid, frankly. He's a fast learner.

Walk me through what happens next, legally. A lot of people seem to think that if you win at the Supreme Court, everything gets magically resolved. But it's a lot messier than that, right?

Understanding that I'm not a lawyer: Let's say they reverse Carpenter, meaning that the previous ruling from 1979 allowing the government to surveil us without a warrant is reversed. Then they would remand [our case] and return it to the appellate courts. Ross would be back in New York in front of the 2nd Circuit, but with guidance from the Supreme Court saying, "No, this was not done properly. This needs to be re-evaluated."

Then I would hope that they would say we'd have a retrial. At the least, I would hope and pray for a resentencing. A few people say, "Oh yeah, he deserves life." I don't think they understand what life is. I don't think they understand that what we're doing to people is torturing them and their families. Most people that I have talked to, though, say that even if Ross is guilty of everything—which I don't believe—double life is just draconian. It's part of a trend that's very alarming in our country. Life sentences have quintupled since the '80s. There are 17,000 or so people serving life who are nonviolent.

One of the reasons I have moved is to be close to Ross. I want to provide to him a lifeline to the outside world, so that [the prison is] not his only reality. That's what happens to people, and then when they get out, they can't assimilate well. It's a terrible system.

How do communications work? You can visit him in person at certain times. Is that the only way you interact?

Most of the inmates have email privileges. They do not allow Ross to have email privileges, because his is an internet crime, or something. But violent gang leaders, who have nationwide networks, they have email privileges. He gets 300 phone minutes a month. He can call us. We can't contact him.

I, and of course his father and our family and some friends, have gotten on a list to visit. You have to go through a background check and all that. In this prison, it's three days a week for five or six hours a day, so I've gotten to have a lot of time with Ross. We're lucky, you know? We have an internet business, so I can do that.

But most people can't, right?

Most people can't. I don't have a small child in school. It's very hard on families. When you see the kids in there, being torn from their fathers after the visit's over and crying, wounded, really harmed by this, it's hard to forget. It's a terrible thing what we're doing to families.

People say prison food is itself a punishment. They say it as a joke, but of course it's not even remotely funny.

I wouldn't say that's a joke. It's certainly nothing you would order in a restaurant, let's just put it that way. Sometimes it's OK, but Ross a lot of times buys food in the commissary and makes his own food. He's doing the keto diet and the keto fasting when he can, and he's staying healthy. But yeah, I mean, prison food is pretty substandard.

Has prison changed Ross?

One of the things about prison that's the most insidious—and Ross and I were talking about this just this past weekend—is how demeaning it is. How you have a loss of dignity as a human being is really intrinsic to the whole thing. Ross says one time he was referred to as "freight." A guard into his radio was saying, "Got freight here coming up." And Ross is like, "Oh, I'm freight now?" Or they say, "We've got some bodies," or they're a number. They're stripped of their dignity as an individual.

Ross hasn't lost his dignity. He's very strong mentally and emotionally. He's reading the Stoics, he meditates, he's a spiritual person. He's staying strong, but it's very tough to keep that sense of who you are. I think people ultimately can be crushed by that.

This interview has been condensed and edited for style and clarity.

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