He is a typical Modern Orthodox teenager from Boston. He comes from a religious family, attends Maimonides High School during the year, and spends summers at a Modern Orthodox camp. He is well-versed in his community’s prohibitions against using technology on Shabbat, but sometimes, he told me, on Saturday afternoons he and his friends “get so bored.” That’s when their cell phones come out, in the privacy of bedrooms or basements, away from parents and other community members.“In the future I would definitely like a day of rest without technology,” said the teenager who, like most students I interviewed for this article, asked that his name not be used, as his parents don’t know he uses his phone—or turns on lights in his room, or writes in his notebook—on Shabbat. “It’s not healthy to be so obsessed with social media. It’s not a necessity, it’s not water, it’s not air.” But for now, he has no plans to keep his phone off throughout Shabbat.That some Modern Orthodox teenagers sometimes break Shabbat is not new. That teenagers might push boundaries in private, with an eye toward returning to the communal norm in adulthood, is likewise not a surprise. But technology is not a youthful fad to be picked up in high school and easily discarded as an adult. Forgoing technology on Shabbat, not being able to use your phone for 25 hours, has become an increasingly dramatic restriction over time, as more and more people read books online, use online maps, get their news digitally, and generally make open-ended social plans based on an assumption that they can contact one another as needed. Today, little in our lives can be done without technology, and as the recent products unveiled by Apple demonstrate, this will only become truer tomorrow.The public conversation around this restriction, and its accompanying struggle for observant Jews, dates back to a 2010 blog post by Rabbi Alan Brill, a professor at Seton Hall University who writes on issues of Jewish identity. On his blog The Book of Doctrines and Opinions he posted thoughts on the term “half-Shabbat,” explaining that it refers to a teenager who otherwise observes Shabbat but who also texts and checks social media. The concept of half-Shabbat deeply shook Modern Orthodox institutions. Brill’s brief post skyrocketed to the top of his most-read entries, eliciting shocked reactions from parents and educators and prompting a flurry of articles. A 2011 story in The Jewish Week suggested that over 50 percent of Modern Orthodox students kept half-Shabbat. A few days later, Dr. Scott Goldberg and Dr. David Pelcovitz, two professors at Azrieli, Yeshiva University’s Graduate School, published a response reassuring the public that, based on their own survey, the number of Orthodox kids texting on Shabbat was closer to 17 percent. This number, however, only served to further confirm the truth of the problem: Half-Shabbat was a new crisis.“I remember thinking, ‘I can’t believe that this the first time I’m hearing about it, and it is already the norm,’ ” said Rabbi Joshua Lookstein, the head of school at Westchester Day School, who attended Ramaz High School as a teenager. “It just felt like everyone was writing about how the best of our kids are texting on Shabbat, and that’s it. As if it was a done deal, a fact of life.”A few years later, the speculative accuracy of this crisis has hardened into unquestioned truth, along with the host of explanations that popped up to explain it (far overstepping Brill’s initial assertions), including many theories that mirror broader societal rhetoric about kids and phones: Teenagers are addicted to cell phones, they don’t know how to live without their devices, and the peer pressure to stay socially aware at all times is unbearable. All except one of the seven Modern Orthodox Jewish educators I spoke with for this article—working in day schools, high schools, college campuses, synagogues, and yearlong Israel programs—assumed that keeping half-Shabbat was a pervasive reality for current high-school and recently graduated students.“It’s so natural to them that even if they know their rabbi says it’s wrong, they’ll say it doesn’t feel wrong,” said one Modern Orthodox high-school Judaic teacher who asked not to be identified, since he was discussing his students. “To not have access to the phone, it’s like choking off their air.”***However, in talking to high-school students themselves, and not their anxious teachers, the reality seems more complicated. A lot of Modern Orthodox teens today would argue that the death of the fully Shabbat-observant teen has been exaggerated, or at least grossly misunderstood. “Honestly, no, my friends don’t use their phones on Shabbat,” said Zoe Ogden, a senior at Yeshiva Atlanta High School. “Obviously, I have friends who don’t keep Shabbat and they use their cell phones, but among my friends who do keep Shabbat, nobody uses phones. I don’t have friends who are in-between.”Shalhevet Schwartz, a senior at SAR High School in the Bronx, remembers when the concept of half-Shabbat first sparked communal soul-searching. “I think people talked about it more than it was happening,” she said. “I know lots of people who don’t keep Shabbat, but it’s not like they would text but not turn on and off lights.” She reconsidered for a moment. “I’m sure there are a few,” she said, “but I don’t know them.”Students and teachers kept referring me to colleagues, friends of friends, cousins, and others who, they promised, either kept half-Shabbat (meaning they considered themselves fully observant with the noted exception of texting and social media) or knew someone who did. Yet almost 20 interviews later, I had trouble finding people who text on Shabbat while keeping all other laws. Of course, some kids I spoke with struggle with using technology, but almost never in the unthinking and unreflective manner that so animated the adult discussion about kids and half-Shabbat. Instead, the particulars of when and what was kept and broken were always part of something more. Unlike other routinely broken rules—sleeping through morning prayers, forgetting tzitzit, wearing a bikini to the beach—using technology on Shabbat is a transgression that comes with a lot of guilt and soul-searching.A Modern Orthodox teenager from the West Coast told me she distinguishes between personal use of technology (looking at Facebook, or reading online) and interactive use, such as texting with friends or making calls: “If you break Shabbat in public, it’s worse than if you do it in private, because you’re hiding from God. When someone else comes in, God comes in, too,” she said. She goes to a Modern Orthodox school, synagogue, and summer camp and plans to spend a year in Israel at a yeshiva before college. She is adamant that the beauty of Shabbat comes from it being a societal break from technology.But every Friday night, after Shabbat dinner with her family, she gets into bed and turns on her iPad, falling asleep to an audio-book. While she does have friends who use their phones on Shabbat, they are mostly not otherwise observant, and the use of the prohibited technology is still a step outside the law that weighs heavily on her. “I feel guilty about breaking Shabbat,” she told me. “I know that I’m guilty, and I’ve suffered emotionally for it.” She paused in thought. “That helps me justify my actions a bit. But it’s just this one thing. I’m a religious person. I believe in God. I believe that the Torah comes from God. But I can’t fall asleep if I don’t listen to my audio-book. I feel like I can hide in my audio-book, but if my friends text in front of me, that really bothers me.” At times, she described herself as “dying from the guilt” of breaking Shabbat, but she can’t stop. She assumes—and hopes—it is a phase she’ll outgrow once she matures, has a family, and raises her own children.Continue reading: Navigating new territoryFor current high-school kids using a phone on Shabbat seems to fall anywhere between kissing before marriage and eating a ham sandwich: It’s definitely not allowed, but the degree to which it ostracizes one from the community is still up for debate.One senior at Ramaz told me that while it would be hard to square cellphone use with the values of Modern Orthodoxy, kids who did so weren’t necessarily outside the group. “If you go to a Modern Orthodox school or a Modern Orthodox shul, then you’re Modern Orthodox,” he said. Andrew Katz, a junior at Frisch High School in New Jersey, who considers himself fully observant of Shabbat, sees privacy as a critical aspect. “If you want to be part of the community you can’t keep half-Shabbat openly,” he said, referencing kids who come to shul with their phone in their pocket, but turned off. While Zoe Ogden agreed that for somebody who attends Modern Orthodox institutions, “there is little you can do to put yourself outside the community,” she added, “if someone said, ‘I’m Modern Orthodox but I use my phone [on Shabbat]’ I probably would say that’s not OK.”***Today’s teenagers are navigating new territory. Even 10 years ago, when cell phones were mostly just phones and maybe took a fuzzy snapshot, their use on Shabbat was perceived with a severity closer to the ham sandwich side of things, according to a range of alumni I interviewed from Modern Orthodox high schools who graduated between 1997 and 2006. “Nobody used their cell phone when I was school,” said a 2005 graduate of Flatbush High School who asked her name not be used, as she is no longer religiously observant. “Maybe I just had good-kid-type friends, but if you were Orthodox, it was just entirely unheard of to use your phone.”Sarah Cheses, who worked as a Jewish Learning Initiative Campus Educator at Yale and is a 2002 graduate of Columbus Torah Academy, remembers reading Brill’s initial post with shock. Using a phone on Shabbat was so foreign from her experience of Modern Orthodoxy that she “almost didn’t believe it,” until she got confirmation from a younger cousin, who had seen Modern Orthodox kids using their phones in Cleveland (though both insist it is foreign to the Columbus community).There are likely a number of reasons cellphone use on Shabbat has become less extreme of a taboo. Perhaps most significant is that phones today do a lot more, especially once they gained access the Internet. While a family computer would be public, and even a laptop bulky and hard to hide if a parent unexpectedly opened a bedroom door, a phone with Internet access is now much more private. Almost all Modern Orthodox kids have smartphones, and a quick update on social media is not only incredibly tempting, but completely discreet. The rise of texting, instead of calling, as the definitive mode of communication made social use even more discreet. A teenager silently texting under the covers risks no chance of being caught, unlike someone making an audible phone call. Most people sleep with their phones close by and are aware of them at all times throughout the day, which is not to say that they turn to them on Saturday because they are addicted, but that kids today are attached to their phones in a way not true even a few years ago.Today “you really need a cell phone, so I understand how even for something like Shabbat, it is definitely very hard to do that without a cell phone,” said a senior at Ramaz High School who doesn’t use technology on Shabbat. Still, he says all of his friends who keep Shabbat don’t use phones or electricity, and he doesn’t know any half-Shabbat kids.Brill connects the loosening taboo around phone use by kids testing the boundaries to the gradual slowing-down of Modern Orthodoxy’s conservatism shift in the 1990s. “We all assumed it would keep getting more to the right, and then it didn’t,” he said, recalling how “there was a certain point in the ’90s when you would never think of having mixed dancing at a Modern Orthodox wedding, and all of sudden people whose older siblings didn’t have it, now, in the 21st century, have it at their weddings.”Some educators recognize that the changing reality of cell phones, and their level of integration into daily social life, requires some innovative thinking. “The crisis here, if there is one, is the lack of a compelling Shabbat narrative,” said Rabbi Ben Skydell of Orach Chaim synagogue on the Upper East Side, who teaches Talmud at North Shore Hebrew High School and the Drisha Institute. “How do you sell Shabbat?”For many, the answer might be in praising the technology prohibitions themselves. “As the world does become more saturated with technology,” said Andrew Katz, “it becomes more important for me to have a space that can be free of that.” The gift of a tech-free Shabbat is a message that rabbis find particularly effective on college campuses and that resonates with many adults. Rabbi Jonathan Kroll, head of school at Weinbaum Yeshiva High School in Florida, is not alone when he says that he cherishes his three-day yontifs, when a Jewish holiday immediately precedes Shabbat, resulting in three days of religious restriction; for him, it’s three days to be free from the tyranny of checking his phone or email. While laws on modest dress, for example, are often challenged with ideology, even the kids who use their cell phones on Shabbat see it as deviant from their own personally held values. Keeping Shabbat free of electronics might be a struggle, but it’s seen as something worth struggling for.As one student said of her Shabbat technology use, “God is not in the room when I do those things.” For now, it’s a practice that puts her outside the boundaries of Modern Orthodoxy, but more important, it’s a problem she wants to fix.***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Shira Telushkin is a student at Harvard Divinity School, studying early Christianity and monasticism.