Photo courtesy of Andrea Matwyshyn

In the early 1980s, Helen Matwyshyn's uncle was run down by a military vehicle while he was crossing a street. The uncle was a veterinarian in Ukraine — which was part of the USSR at the time — and a critic of the Communist Party. The family suspected that it had  been an attempted assassination, but he survived, suffering broken bones and permanently shortened legs. Matwyshyn's mother got the news about the accident in a letter written by a cousin in Ukraine who sent it to a person in Poland who hand-delivered it to another person in Poland who mailed it to a family friend in Chicago who then delivered the letter to its intended recipient, Helen's grandmother. The roundabout method of delivery wasn't because that was how the postal system worked then; it was to evade government censors in the USSR who closely monitored written communication, especially letters being sent or received from people based in the States. Even going through a contorted delivery system, the letter was still taciturn, saying simply, "He had an unfortunate sidewalk incident. He wasn’t watching where he was going and stepped out.”

Over the past year, we've become hyper aware of the extent to which Big Brother is able to shoulder-surf our digital communications. The NSA documents leaked by Edward Snowden have shown how intelligence agencies run mass-collection programs to gather information about phone calls, texts, emails and even Facebook messages, leading to new calls from privacy advocates for better encryption practices and tools.

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While the way we communicate has changed over the years, the concerns about government monitoring have been a constant. In the 1990s, early Internet adopters calling themselves cypherpunks started coming up with — and trying to popularize — tools to preserve privacy online, a movement excellently documented in the book This Machine Kills Secrets. Among their creations were anonymous remailers which, like the privacy-enhancing browser Tor, cloak a network in secrecy to make it less clear who is sending what to whom. With remailers, designated servers act as middlemen for email messages, accepting them and sending them along without revealing where they came from so the sender can remain unknown.

Before the digital version of 'remailers' came along, there were IRL ones. Helen Matwyshyn's family — a group of Ukrainian immigrants who came to the U.S. after World War II ended — created a remailing network to exchange uncensored news with loved ones who remained in the former Soviet Union where mail was closely monitored. The family hasn't told their story before. Those involved didn't talk about it with strangers when the network was active — from the 1960s until the early 1990s —  for fear of its being discovered and disrupted. If such networks were set up by other immigrant families, they do not seem well-documented.

"After the war, people who fled the regime wound up wherever they wound up in the free world," says Olenka (Helen) Matwyshyn, who now lives in Chicago. She was born in Ukraine in 1938, though her family left the country when she was a toddler. "We had to move West and escape because my parents were not considered friends of the regime in the Soviet Union. My father was a business leader and was put under house arrest for 'not being a person of assistance.' We were on the list to be imprisoned and taken to labor camps in Siberia. We barely escaped."

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Targeted for political reasons, they moved westward through Czechoslovakia and Germany, settling in a refugee camp in Bavaria, where they were located when the war ended. They immigrated to the U.S. in 1949 when Matwyshyn was 10. Her family lived first in Philadelphia for six months and then her father got a job in Chicago. "Everyone who came to the States was anxious to link up with friends and family back home but everything was monitored," she said in a telephone interview that included her daughter, Andrea Matwyshyn, a lawyer and professor who specializes in technology issues and first told me about her family's IRL remailer network.

Letters were regularly read by authorities in the former Soviet Union, and letters from the U.S. were especially subject to monitoring and censorship. When Matwyshyn's family first started sending letters back and forth between the U.S. and Ukraine in the 1950s during the beginning of the Cold War, there were so many black-outs that they were unreadable. Matwyshyn's family has not kept the letters, but the black-outs looked like this:

Example of censorship during World War II: a 1944 letter in the USSR.

They realized they needed to send letters in roundabout ways. Any letter sent directly between the U.S. and Ukraine would be heavily censored, but if they could find people in other countries to act as go-betweens, then they might be able to exchange news that wouldn't get blacked out.

"If you were writing from the U.S. directly to Ukraine, it would raise suspicions. But if it was emanating in Poland and going to Ukraine, it wasn’t at the top of the censors' list to check because they were both under Soviet rule," says Matwyshyn. So Matwyshyn's mother Maria (pictured above) and grandmother Olena began a letter-writing network. They started a second network with a family friend named Natalia who also lived in Chicago, who wanted to communicate with a brother in Czeckoslavakia.

The intermediary country Maria and Olena used for letters to Ukraine was Poland, which was less suspicious of letters coming from the U.S. The chain could get complicated. For example, an uncle in Ukraine might send a letter to a person in Poland who would hand-deliver it to someone else who would send the letter to a cousin in Cleveland who would send the letter to Matwyshyn's family in Chicago. The human chains through which they sent communications became pretty set, through they would replace "nodes" in the chain if someone came under suspicion—as when Matwyshyn's great aunt's home in the Ukraine was raided by police who scoured it and read every letter they could find—or when a participant grew too old or sick to take part.

They would either send one long letter that subtly addressed multiple people or a letter with a second letter in a blank envelope. The letters were signed with pseudonyms and contained codes that indicated to whom the rest of the letter or the inner letter should be sent on. They needed to make it hard for any government official who reviewed the letters to discern the true origination point and final destination of a letter. At the last step in the chain, the letters were often hand-delivered, sometimes tucked into a newspaper or book.

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For those familiar with privacy-enhancing technologies like Tor, this will sound familiar. It's the analog version of how that tool works, sending traffic through different nodes so that what Alice's computer gets from Bob's server can't be detected by an outside observer.

The letter writers even used a kind of low-level encryption. "Things and people wouldn’t be called by their name specifically," says Matwyshyn. "Stalin would become Uncle Vanya, or some innocuous name, so it would look like they were talking about their families when they were actually talking about politics. You couldn’t say, 'I hope you aren’t hungry;' that was seen as politically sensitive because of the famine under Stalin. The Soviet Union would not allow that kind of depiction of life there. They wanted all external communications to reflect a country where everyone was happy and laughing."

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The remailer networks were sometimes used to break news of family members' deaths; Matwyshyn's family learned through the network that an uncle and a great uncle—a lawyer and a priest—both died in imprisonment after the war. People in the U.S. wanted to know if relatives sent to work camps in Siberia were still there and were still alive. "That kind of news was just barely in the letters," says Matwyshyn. "It had to be communicated in a way that didn’t seem like an indictment of the regime doing something horrible to a person. So it had to be said that, 'So-and-so came back from working on Uncle George’s farm.' No last names were used, just nicknames, first names or code names. But that meant they were back from imprisonment."

The remailers were dependent on people in Soviet countries being willing to take risks to help people they might barely know. To avoid scrutiny from authorities, the network needed as intermediaries people who seemed innocent—who had no direct connection to exiles or to citizens who appeared 'unsavory' to officials; they were the only people who could receive and send letters that wouldn't be heavily scrutinized. "You’d pick the family member with the least controversial last name to be part of the network, because last names often triggered searches," says Matwyshyn. "If the networks had been discovered, they could have lost their jobs, maybe even their lives."

The remailer wasn't perfect. Sometimes letters would go missing, which correspondents would only realize when someone referred to something in a previous letter that they had never read. And the letters were often hard to decrypt. "My mother and her cousin would pore over the letters to decipher family codes and nicknames to understand who they were talking about," says Matwyshyn. "Sometimes you couldn’t make heads or tail of it."

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It was the historical equivalent of forgetting the password for your encryption key.

The letter writers from the U.S., with younger members of the family

Matwyshyn's family network was most active in the 1960s and 1970s when the ties between those in the States and those back in Ukraine were the strongest. Phones became prevalent in the 80s, but they were extremely wary of using them. "You would hear clicks if you talked from the U.S. to there," she says. "You knew you were being surveilled. Sometimes your phone calls would be interrupted totally. You would not transmit any important information or say anything that was politically unwise. Paper was more trusted than phones because the latter were completely surveilled, and because you could disguise the true sender and recipient with mail."

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The networks remained in place until the early 90s when Ukraine became independent, says Matwyshyn, meaning three decades of using this elaborate and complicated communication system. "The letters got better in the 80s. When the Soviet Union fell apart, it was much easier," says Matwyshyn. "For me, it was like seeing things for the first time and discovering a new country. By 1995, it was wonderful to be able to write something that was not coded. My mother especially appreciated that as the chief letter writer."

Our current privacy tools for communication seem incredibly easy compared with the painstaking and time-consuming way Matwyshyn's family went about it. Digital encryption tools can be hard to use but they are getting simpler and we have a range of options that have been developed to try to ensure the privacy of communications—whether it's Tor for web browsing, the Signal app for encrypted phone calls, PGP for email, or Adium for chat.

Lance Cottrell is a privacy technologist who developed one of the best early anonymous digital remailers: Mixmaster, released in 1993. A digital version of the Matwyshyn's family remailer, Mixmaster introduces additional nodes in an email communication chain, strips off identifying information from messages, manipulates them so that all messages that come through the service are the same size and then sends them on; it makes tracking the provenance of an email incredibly hard. It theoretically would let a whistleblower emailing a journalist remain anonymous, but like any tool, can also provide a shield for wrong-doers, as when a Mixmaster account was used a couple of years back to send bomb threats to a university.

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Cottrell says that he had heard about physical mail forwarders before—usually in the context of drug smuggling—but nothing "done at scale." "It does seem like an obvious thing to do, if communications from country A to country B are under close observation, go through neutral country C to avoid attention," Cottrell, who is now a chief scientist at NTrepid Corporation, said by email. "The Cypherpunks were very active in creating anonymous remailers because email provides so much tracking info and opportunities for interception. PGP was already out and providing security for the message contents, but not the transactional information."

Another Finnish developer of a digital anonymous remailer released in 1995 told Wired he was inspired to create it in part by the intense monitoring of who-said-what in the former Soviet Union, calling it "appalling" that the government should be able to perfectly track such things down.

This immigrant network had to get creative in its 'infosec' or news simply wouldn't have gotten through. "People are inventive in desperate times because their need to communicate with family and friends is so important," says Matwyshyn. "You have to deal with difficult situations. No matter what calamity befalls you, you find ways to connect. People get inventive and are creative in the face of great need."