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At 8 a.m., the first bell rings, signaling the start of classes for Heather Scott’s 26 chattering students, who begin trickling into her classroom. Some clutch thermos bottles and plastic bags filled with Asian pastries as they take their seats around the rows of desks she has arranged. Most are bundled in big winter coats, scarves, and gloves that they either throw over the backs of their seats or don’t take off because the room feels cold. The collision of Mandarin, Cantonese, and other dialects is foreign to the teacher’s ears, but there is a Chinese word she readily recognizes by now.

“Finish the paragraph about the picture,” Ms. Scott says sternly once the students have settled down. She enunciates every word in a persistent tone, glancing around the room as she reads the directions off the Smartboard. This is a level one class, designed for students who only began to learn English at the start of the Fall 2013 semester. After a moment of silence, one student seated near the front of the class responds, “Shénme?” Immediately, Ms. Scott snaps back, “You, shénme!” This playful interchange sets off an eruption of laughter from every Chinese pupil in the class. Even the lone Bengali student chuckles shyly to herself.

By now, both she and Ms. Scott know that shénme is Chinese for what? There’s no more common word in this classroom of mostly Chinese transferees. They are among the 12,000 immigrant youths who have emigrated from China and entered New York City’s million student system, known as English language learners. With immigration from China on the uprise, ESL, or English as a Second Language education, is more crucial to this city than ever.

Inside Lower East Side Preparatory from Susan Cheng on Vimeo.

At Lower East Side Preparatory, 570 students spend anywhere from one to three periods of their school day learning English. Fully 65 percent of them are from China. Famous among the Chinese-speaking community in New York, this Lower East Side institution is what is known as a transfer school, meant for those between the ages of 17 and 21 who have previously dropped out or fallen behind in high school credits. It is ideal for those who have just moved to the city and know little or no English.

Although schools like Lower East Side Prep are among the best in the city at preparing English language learners for college, the challenges that impede student progress are daunting. They include the constant temptation to revert to native languages both at home and at school. Many lack family support so coping financially often ends up taking precedence over their studies.

Those who attend Lower East Side Prep are students like 16-year-old Minci Chen, who moved to New York last October from a small town in southern China’s Guangdong province. A month later, family members introduced her to the much-lauded high school, where she was placed in Ms. Scott’s class. From my weeks of classroom observation, it was clear that Minci is one of the dozen or more of Ms. Scott’s students who are most eager to learn the new language. Although she doesn’t often raise her hand, her bespectacled eyes are always lit and she listens intently to her teacher, diligently copying vocabulary words into her notebook. She keeps up with the class, sometimes with the aid of a dictionary or through an exchange with classmates. But outside of school, she struggles to use what she’s learned.

In animated Chinese, with a touch of a Cantonese accent, she explained: “Whenever I’d go out shopping or to the store with my sister, everyone would speak English, and I’d feel doomed because I had no idea what people were saying. Even buying something at the store felt like the greatest challenge. Last week, for example, I went with my family to buy shoes, but we didn’t know the word for ‘boots.’ I had to use my hands to gesture until finally I learned the word ‘boots.’” Although she is frustrated, her voice betrayed no exasperation. On the contrary, she continued to chatter on, giggling at herself every now and then, admitting that she is happier here than she was in China, even with the language barrier.

Minci lives in Bay Parkway, Brooklyn with both her parents. Her father works in a Chinese restaurant and her mother at a factory. She has it easier than most of her classmates, who work after school and on weekends. Her only obligation is to study hard and make good grades.

Chongyan Peng, who I found inside Mr. Weimin Peng’s classroom at lunchtime, buses tables every Friday after school and on weekends at a sushi restaurant on West 23rd Street. Three days of work a week is a lot to carry in addition to a full course load. During the weekends when he works all-day shifts, he doesn’t get back to his home in Flushing until 1 a.m. “On Sundays after I work, I go home only to have to get up for school at 6 a.m. again,” he told me during fifth period, when most of the students have flocked to the lunchroom.

Chongyan uses the lunch period to avoid the school’s crowded and noisy cafeteria. Instead, he goes to Mr. Peng’s classroom, where the older, college-bound students congregate to work on SAT practice questions or study together. While Chongyan is still a few years away from college, he likes to eat his cup of ramen noodles in the classroom’s relative peace while he browses the Internet on his smartphone. “Whenever and if I ever get a free moment, I’ll just sleep,” he said, laughing. His Mandarin has a thick coat of Fuzhounese, a remnant of life in his home county of Changle, which he left with his father and older brother only two years ago.

For Chongyan, there isn’t any pressure from his family to work; he does so simply to feel more independent and to help out when needed. His restaurant gig can earn him up to $100 a day, most of which he saves. “If I make a lot, I’ll give half of it to my family, depending on the situation. I don’t really spend it on myself. Once in a while I’ll spend it on breakfast or if I go out to eat.”

Other students, like 20-year-old Bingjun Cao, must fend for themselves. Bingjun’s parents emigrated from Beijing to the the United States without him when he was only two years old. They left him in the care of his grandmother until he turned 16, when his parents wanted him to join them in New Jersey. After some encouragement from his grandmother, he agreed in 2010. But the arrangement lasted only about a year. He is vague about the details, saying not much more than that he moved out.

“They left me when I was two years old, so we had big problems—generational gaps,” Bingjun said in perfect English. “They're old school, so it’s hard to communicate with them.” As a student in ESL level five, he not only speaks with more confidence and a broader range of vocabulary, but there’s also a trace of agitation and fatigue in his voice, like he’s tired. Perhaps that’s because he has that much more responsibility.

When the school day ends at 2:39 p.m., Bingjun makes a 45-minute commute to Queens, where he works full-time at a Popeyes restaurant. That affords him a living and enough money to pay his half of the rent on a Chinatown apartment in Manhattan, which he shares with a classmate. “When I came here, they talked about the American Dream—working hard to achieve the goal,” he said. “Now I’m lost. I don't know what my goals should be. Of course, I need to find a better job, get good grades, go to college. Now I think it’s hard to go to college. Sometimes, I’m really jealous of people who have a good mother and father, who only have to study.”

Things aren’t necessarily so much easier for students like Ms. Scott's pupil, Minci, who come from intact families and aren’t expected to work. Their parents often do not speak English, obliging the children to take on the sometimes awkward role of interpreters. Minci’s parents can speak a little English but not enough for most situations. “I’m their translator when words are too complex,” she said.

John Hunt, an immigrant education expert, has observed experiences similar to Minci’s through adult English learners in his classes at LaGuardia Community College. He also teaches parents of English learners how to navigate the city’s school system. Often, parents who don’t speak English have a hard time even getting their children enrolled in school.

The biggest problem is when parents can’t get enough or understand enough of the information they need, especially in situations where there is no one to translate. Although the city’s Department of Education offers various translation services to parents with limited English proficiency, parents often are unaware of the resource, and it isn’t always available exactly when it is most needed. “So the children end up becoming the interpreters,” Hunt said, “which is just not fair to put a young child or adolescent into that position.” Beyond academic concerns, the students assume a role of authority in other ways too, some of the teachers told me. For instance, whenever the house phone rings, it’s the children who have to answer. Some have to check medical prescriptions for other family members or help them navigate a city full of signs they cannot read.

“My mom works on 8th Avenue in Brooklyn,” Minci said. “The first day she had to go to work, nobody helped her, really. I told her what roads to take, how many stations to pass, and where to get off. She eventually found it on her own after I’d help her find a map on the Internet.”

   

In November of last year, hundreds of teachers from New York state gathered inside the Crowne Plaza in downtown White Plains for the 43rd annual conference of the New York State Teachers of English to Speakers of Other Languages. In one room, two high school teachers discussed their experiences in the classroom while also touching on the complexities of identifying a student who requires ESL training.

The New York State Department of Education has specific mandates for determining whether a new student is an English language learner or not. Within the first 10 days of a student’s enrollment in a public school, the parents take a survey called the Home Language Questionnaire, available in English, Chinese, and 13 other languages. It contains questions such as, “What languages are spoken in the student’s home or residence? What languages does your child speak?” If the parents indicate that their child speaks a language other than English, the student is then likely to be given the New York State Identification Test for English Language Learners. Commonly known among educators as the NYSITELL, this exam is an improved version of the previous test, the LAB-R, which prospective English language learners took before NYSITELL came into effect in February 2014. If students score low on the exam, they are labeled an “English language learner” and placed into an ESL class.

One university professor who sat in on the presentation mentioned that many of her students who graduated from an ESL program in high school often struggle with the transition to college. The special language student label sometimes stigmatizes them.

“They need to be in an environment where they don't feel like they're stupid. They need to be an environment where they are encouraged and not discouraged, where they are free to make mistakes,” the professor said, adding to the two presenters’ discussion on how to best accommodate an ESL student. “Sometimes ESL students in college feel like, 'I'm in this program because my language is not good.'" Why ESL students feel this way remains unclear, but hearsay among parents can be a factor, sometimes perpetuating misinformation about these programs and the stigma as well.

One of the high school teachers who gave the presentation mentioned that she has also encountered and heard of cases where longtime residents of the city tell immigrant parents: “You don’t want your kids in ESL.” Some immigrant parents will go so far as to claim that English is spoken at home, when it is not, in hopes of getting their children placed out of ESL into regular English classes. If the parents are successful, their children can then bypass the language assessment exam that follows the questionnaire and be placed into a mainstream English class. This in turn can sometimes be more detrimental to their learning than beneficial, especially if the student has a learning disability.

Hope Sterns, an M.A. candidate at Columbia University’s Teachers College, points out another inherent issue that educators have found with the survey. The questionnaire neglects to ask if the student has any learning disabilities or a low literacy level in his or her own language. That lack of information could easily cause a misinterpretation of low test scores, she said, which might seem to indicate the need for ESL training when the results actually call for other forms of remediation.

Actually, there is a failsafe built into the system, but it too often fails. The State Board of Education recommends that ESL educators conduct informal interviews with prospective students in their native languages before the exam is administered. But the interview is often skipped for whatever reason, teachers at the conference told me.

Sterns said anyone who actually conducts the interview would be able to recognize if the need was special ed or ESL, whether the student needs help with spoken English or with literacy more generally, even in their native languages. Some students may even have the compounded problem of no English, low literacy skills, and learning disabilities.

It’s not much of a leap to think that literacy and learning disability issues might also be prevalent in the language-learner population. The 2003 National Assessment of Adult Literacy, the latest study to survey the literacy of U.S. adult citizens since 1992, found that 30 million adults had “below basic” prose literacy. In addition, a report by the National Center for Learning Disabilities also found that 2.4 million students enrolled in public high schools were diagnosed with learning disabilities in 2009.

Richard Ciriello is an ESL teacher at Lower East Side Preparatory with a background as an occupational therapist whose previous practice involved many handicapped and learning disabled students. He thinks the more prevalent diagnosis of learning disabilities reflects both the greater awareness educators have of these issues and the higher standards of education being imposed in the public schools. Higher standards also have hit the job market. Ciriello cited as an example the current qualifications needed for a position as a city sanitation worker. They must have a high school education and need to pass a written exam.

“The more literacy demands you put on people, the more now you're gonna see the neurological range in human beings and that the environment determines what makes people learning disabled,” Ciriello explained. In order words, when jobs and schools demand a higher level of literacy from people, the more learning disabilities become apparent.

Mr. Ciriello’s classroom, which is just a few doors down from Heather Scott’s, is just as rowdy as Ms. Scott’s before the seventh period bell rings. After he counts down from five to zero, the 33 students in his level two ESL class pipe down to hear his instructions. Their assignment for the next three periods that day is to survey the modes of transportation each student uses to get to school in the morning, which they later convert into presentations.

Since it is after lunch time, most of the students are energized from a meal or nap and chatter in loud animated whispers. Two or three others, however, seem drained. They stay silent, looking blankly at Mr. Ciriello who lectures with enthusiasm. As students in ESL 2, they’ve moved on from learning basic English to tackling the academic English required for college-level work. Conversational English is one thing, but to develop academic English skills is another altogether, Ciriello explained, in between checking up on his students’ progress.

“Many of them want to go to college, and I'm mandated to make all of my students college and career-ready,” he said. “I want to do that—so there's all these layers of trying to get students from where they are to making them . . . ready in terms of language.” This requires him to repeatedly assess their progress, their strengths and weaknesses.

“But then on top of that,” he said, “I need to look at their language. In education, language is the tool for imparting information and for also making sure that students understand information . . . the very tool that they need to show success is the tool that I have to teach them."

But here’s the rub: to fully acquire academic English skills takes anywhere from seven to 10 years, a span of time the students at Lower East Side Prep do not have.

As one period goes by, the students transform the data they’ve amassed in their surveys into colorful bar charts on drawing paper, which they later present in groups of four. One particular student stands out. With his eyes glued to the teacher, he participates actively and speaks with more confidence than his peers. When his group is sent to the whiteboard, the sentence he has written is nearly perfect. Unlike most of his classmates, the 18-year-old has given himself an English name. He introduces himself as “Shawn Zhang.”

“I didn’t really have a formal education,” he told me the next day at lunch. In between scoops of mashed potatoes, he reels out the different schools he attended in Hunan province, where he was born and reared. “I’ve always changed schools a lot because of my mom’s jobs,” he said. At one point, he even attended a school where they taught skeet shooting, of all things. “When I was living in China, I didn’t get the foundation I needed,” he said, “but I work hard now.”

Working hard means studying much harder than he did in China before coming to the States in 2011. “When I first came here, I only knew A-B-C-D,” he said, smiling sheepishly before taking a gulp from his carton of milk. “When I lived in Rockland County, I would hang out with American kids and speak with them, but I would rarely write it—that’s why my spelling is poor.”

Now that Shawn lives in the city, however, he has less opportunity for casual conversation in English. Most of the people around him, including his peers, are Chinese and tend to revert to their native language. “My first feeling when I came to this school was like I was back in China,” Shawn said, echoing a sentiment I heard over and over again from the students at the school, like Bingjun. When I ask the 20-year-old his impression of Lower East Side Prep, he told me that it’s very different from the private school he attended during the brief time he lived with his parents in New Jersey. If it hadn’t been for the troubles at home, continuing at the private school would have been his preference.

“First off, for those of us who immigrate here, we come here mainly to try and immerse ourselves in a new environment,” Bingjun said, this time in Mandarin. “Now that I’m here, I don’t see that. I see everyone speaking Chinese. Everything is the same as China. Chinatown is just like China . . . there isn’t a difference that feels new or stimulating, nothing that makes me more curious or that I like it more,” he said. His articulateness suggests that this wasn’t the first time he’s voiced these frustrations.

When I asked him if living and attending school with all or mostly Chinese students has helped his transition to American life, his response struck me as wise and insightful. “I don’t know if you know this saying: rén wú yālì qīngpiāopiāo (人无压力轻飘飘),” he said, calling to mind the tone of a parent. It means that a person without pressure will merely float on slowly. In other words, if English language learners like Bingjun aren’t pressured, they will not learn English quickly.

From the looks of recent studies, Bingjun may very well be onto something. In 2013, two Purdue researchers, Brigitte Waldorf and Raymond Florax, found that immigrants who choose to live and work in ethnic enclaves are more likely to continue speaking in their native tongues. While Chinatown may be more comfortable for an immigrant who has just arrived from Fujian province or Hong Kong, the familiar environment may slow the assimilation process.

On the other hand, Hunt, immigrant literacy expert, believes the effects of ethnic enclaves are more nuanced. “The obvious answer is that the more you’re exposed to people who don’t speak your own language, the faster you are going to learn,” he said. “I wouldn’t say that you are more motivated, I would just say that there are more opportunities to learn English.” But on arrival, he said, other needs may well take precedence over language.

“Housing is one of them; you generally use your network to find housing options,” he said. “Obviously, the thing to do when you first come here is to network with your ethnic community. I wouldn’t say that immigrants want to isolate themselves. I think it just makes more sense at the beginning when they arrive.”

John Casey, a professor at Baruch College who previously worked for the Mayor’s Office of Adult Literacy in New York City, added that ethnic enclaves provide other important benefits for newcomers. “They form because new arrivals want to live somewhere where they can find their services and because of ‘chain migration,’” he said.

Lower East Side Prep, under the guidance of its principal, Martha Polin, has taken steps in recent years to diversify its student body. Years ago, before Bingjun had even come to the United States, the Lower Manhattan school consisted of roughly 95 percent Chinese immigrants. Now, that number has dropped to 65 percent with 20 percent of the school's English language learners arriving from Spanish-speaking countries, and five percent from places like Haiti, Ghana, Yemen, and Bangladesh. The other 10 percent are not new immigrants, so students do have the opportunity to interact with non-Chinese schoolmates during the school day. Even with this concerted effort at increasing diversity, Ms. Polin acknowledges that the propensity of students to stay within their ethnic affinity groups, is powerful.

"So even when half the class is, let's say Spanish and American, [and] half the class is Chinese, they don't talk to each other,” Ms. Polin said. “It's really hard to bridge the cultural divide. But it's more them than us. In other words, the opportunity exists for them to speak English plenty, but they don't use that."

They don’t, but then again, it’s hard to pass judgment on such a reflexive, effortless act as speaking in a native tongue. Although not immediately apparent, some of the benefits of this instinctual response may actually outweigh the detriments.

Mr. Ciriello agreed. “I think that a lot of times what the students don't realize is, you're coming from another country, you're coming from a place where we don't even have the same writing system let alone words that are kind of similar,” he said. For newcomers especially, “it’s probably best to start in a place where you shift from using your native language a lot of the time to little by little, using it less and less.”

While some students may have the determination and diligence to thrive in a regular high school, it doesn’t seem likely for those who are just learning the foundations of English. “What if you were in ESL 1 or 2 and everyone around you were speaking English and you can’t,” Mr. Ciriello said. “Nothing says that you are going to be successful in that environment.”

Alan Werner is an educational consultant for Lower East Side Prep, who spent 10 years working for the Board of Education. Even though his own father benefitted from a full immersion experience when he immigrated from Poland many years ago, Mr. Werner doesn’t think it works any more. “There are some hardliners who talk about turn-of-the century immigrants who only learn English through full immersion—thrown into society, thrown into schools,” he said.

The problem with trying to implement that today is the wide range of student backgrounds. Some hail from large cities, where they’ve had prior schooling and dabbled in English classes; others come from the countryside, where they took on jobs instead of furthering their education. There was a time when affluent families from big cities like Hong Kong and Beijing would send their children abroad to study at Lower East Side Prep to improve their educational opportunities. But today, most of the students are immigrants from poorer regions like Fujian, where making money is valued over learning.

Another disadvantage of full immersion is how mentally exhausting it can be for a new learner. Victoria Rasinskaya, who has been teaching ESL at Lower East Side Prep for about five years, gave this example: “If you travel in a foreign country, you feel very tired. Why? Because you try to read all the foreign signs,” she explained. “The specialists say, ‘Stop reading the signs. Just relax. Don't read the signs otherwise, [you’ll] be tired.’” This is why she and many other teachers at the school choose not to enforce a strict no-English rule. “If they say a word or two in Chinese, I don't think it’s going to harm them. It’s a release. Otherwise, in eight minutes, the student goes on vacation: you don't understand, you don't want to, and you don't care.”

Another issue is the lack of outside English reinforcement of what is being taught during the school day. Mr. Werner noted how often students return to environments where only their native languages are being spoken. “Even the places these students work are often based in places like Manhattan’s Chinatown and Flushing. They come back [to school] and have to re-adjust to the English. It’s not that it’s becoming inherent in their speech.”

Lack of self-assurance also confounds the learning process. “I think to some degree, it’s a confidence issue because I think their receptive language is a lot better than their expressive language,” Mr. Werner said. “I’ve been in classes here, where I’ve seen students who really understood what’s being said but, when called upon . . . perhaps didn’t have the confidence to make the attempt to respond. And then they would respond in Chinese to their fellow students, who would then translate it to their teacher.”

It was my impression that most Chinese students at the school would feel more inclined to speak up in an environment of peers who speak their native language, but not Yanling Zhang. “I'd rather move to place with more Americans, which would be good for our speaking and our studies. Everyone in my classes are Chinese,” she said in a small voice that surprised me.

When we first met in Mr. Peng’s classroom, Yanling struck me as tough and standoffish. She glanced up at me with an icy gaze when I approached her desk and then looked back down to punch away at a video game on her Smartphone. The next time, when we met in the library, she put her phone away and opened up a bit more. Slouched back on a seat in the corner, she seemed exhausted. On school days she goes from Lower East Side Prep to her job as a Chinese language teacher’s assistant in Chinatown.

“In a given day, I won't say even 10 sentences in English,” Yanling said, “so my speaking is pretty poor.” Yet it seemed the biggest block was her fear of the judgment of her classmates.

“Yesterday I was in my speaking class; we were having a debate,” she said. “If you said something wrong, if your grammar was wrong, the rest of the class would laugh at you. It's awkward, so I'm scared to speak.”

It doesn’t help that most of Yanling’s school friends have already graduated. While she knows most of her classmates, she doesn’t consider anyone a close friend now, a situation that makes learning English and staying motivated more difficult.

Teresa Devore, after 10 years of teaching at the school, understands the reasons for Yanling’s reluctance.

“In the activities that I do in class,” Ms. Devore said, “I try to help them make connections to their peers; they're not allowed to just sit silently and be in their own little worlds. But those who are hard to reach and hard to keep motivated are the ones who don't have connections to other people in the school. Those who drop out—often they didn't make good friends here, and they [didn't] have people pulling for them here. But those who have made connections . . . they drink the juice of education, and they want to make their teachers happy.”

   

Family life also plays a role in how fast a learner masters English. A study conducted by Suet-ling Pong and Nancy S. Landale, two researchers at Pennsylvania State University found that the education level of parents before immigrating has a more significant impact on their children’s English development than any other socioeconomic factor. How often a parent will read to his child, for instance, is directly related to the parent’s level of education before moving to a new country.

Casey, the Baruch College professor, experienced this himself, having immigrated with his family from Hungary to Australia at the age of two. “If the parents see education and English as important and instill this in their children, and the children have access to quality education, then they will learn,” he said. “My parents valued education and we [lived] in a neighborhood with good schools.”

Unfortunately, only about a quarter of the students at Lower East Side Prep have the support of a family. Some, like Bingjun, share an apartment with classmates. Others live with distant relatives, who don’t usually offer a lot of support. Even those who live with their families sometimes don’t find a lot of encouragement.

Of those who live in the city with their families, only half have understanding parents who encourage them to finish school, Ms. Polin told me. “ . . . half of them are constantly telling the kid, ‘Why don’t you quit school and go to work?’”

Many of the students do, in fact, leave school to take on part-time jobs. Weeks before I interviewed Mr. Weimin Peng, he told me of a subway encounter he had with a former student who had dropped out of Lower East Side Prep. He couldn’t pass his English Regents examination, a standardized test most students across the state of New York must pass in order to graduate. “So he's working in South Carolina at a sushi restaurant,” Mr. Peng said of his former student, who was in town on a visit.

The Regents exam, Mr. Peng said, “is very hard—definitely very hard.” Although 86 percent of students at the school pass the English Regents annually, it’s still the most difficult challenge for the language-learning group. They can take all other tests—Math, History, and Science—in one of a slew of languages, including, Chinese, Spanish, Haitian Creole, Korean, and Russian. Mr. Peng runs the Regents prep program for the ESL students and always feels “very proud of them if they pass.”

For some students, no hurdle is too high. As Ms. Devore explained, “They want a better life. They recognize that they don’t want to follow in their parents footsteps. . . . some of them feel pressure from their families to go to college, and that’s enough to make them want to go to college and make them want something better, but some of it is something more intrinsic. They expect something of themselves.”

Some former graduates have gone on to finish college and come back to Lower East Side Prep as teacher’s aides. Iris Chan is one of them. She left her home of Guangzhou and enrolled in the transfer school back in 2004 and has since graduated from Brooklyn College with a degree in Childhood Education and Studio Art. She returned to her high school to help out Ms. Scott and Mr. Ciriello in the lower level classes. Ms. Polin said hiring former students to come back and help is “almost my best advertisement.”

   

I returned to Ms. Scott’s class some weeks after my first visit to find the students reviewing the negative form. The lesson seems straight forward enough to me, but when older material on the past tense and subject-verb agreement get thrown into the mix, the warm-up exercise becomes trickier for these English beginners. As their teacher takes attendance, they work on negating the sentences displayed on the Smartboard. Meanwhile, Iris weaves in and out of the rows of desks to check on the students’ progress, giving assistance whenever necessary. Some of them prattle on loudly in Mandarin. The more sleepy-looking ones mumble to themselves, sometimes through a yawn. Though some sit unengaged with their heads resting on their hands and blank expressions on their faces, the more studious ones are hard at work. Next to me, Minci furiously erases what’s in her notebook and thinks to herself before jotting down a new answer.

A few moments later, I see Iris take a student who had been slacking off to the back of the classroom. When she asks him to negate each of the sentences as instructed, he wears a look of both embarrassment and smugness. His response is chock full of “ums.” She cuts him off with a stern, “Don’t ‘um.’ Answer the question.” Finally, he attempts the exercise.

Sighing slightly, Iris appears exasperated. “I've found that a lot of kids like to dream,” she said. “They say they want to be an editor, but what they don't realize is that they need to know English, and they won't work hard to learn. . . . They don't know they have to put a lot of effort into it to make their dreams come true.”

Despite the frustrations with teaching new learners, she’s optimistic. “When I was in ESL 2, I was like the kids in ESL 2 now, unable to communicate,” she recalled. “Our English was mechanical, ‘robot’ English.” When I ask how she grasped English so quickly, coming as she did as a 17-year-old from Guangzhou province, she mentioned her art books and painters such as Mary Cassatt, Manet, Monet, and Georgia O’Keefe, and how learning them and other such pastimes sped up her learning process. “I listen to English music, watch movies,” she said. “Any time I don't understand something, I'll hit pause and copy down the vocabulary words. Afterwards, I'll rewind, go back to the last . . . and try to understand.”

Ms. Devore said for many of the students at Lower East Side Prep, seeing what their parents have gone through to come to the United States and send them to an American school is a prime motivator. “The students don't want to let their family down, which is inspiring . . . they have so many barriers up around them, . . . yet they're still strong enough, mentally and emotionally strong enough, to do it,” she said. “Those are the kids who stay here for the duration, they graduate, and they go on.”

Those who do not make it to graduation are predominantly those who drop out to help their families make ends meet. It’s usually not by choice, assistant principal Samantha Dong explained, although there are some exceptions.

“No kid is like, ‘Oh I don't want go to school anymore; I just want to hang out,'” she said. “It’s more like, 'My family needs me to work, and right now I have to prioritize making money and supporting my family or supporting my kid and my livelihood before school.’”

But other times, such as with the student Mr. Peng encountered on the subway, the reason can be the repeated failure to pass the Regents in English. In other cases, Ms. Polin said, it’s a student who never intended to complete the program, the ones who come “to learn survival English, get Metrocards, get free breakfast and free lunch.”

Mr. Werner said for at least some members of this group, the importance of staying in school and getting a high school diploma comes only after they have worked for a period of time. And then some of them actually do come back.

“One mindset is [that] you come here to make money. It’s America,” Mr. Werner said. “The other mindset is that you come here to take advantage of the educational system.” Both goals speak to the desire for a better life, he said, however, “How you define that improvement sometimes doesn't really come to fruition until you get to that place and see exactly what the offerings are. For some, it’s get to work. For some, it’s get to school.”

Johnny Zheng experienced this first-hand after moving from Fujian to New York City nearly four years ago. When I approached the 20-year-old in Ms. Devore’s ESL 7 class, he and the rest of his peers were researching scholarships on NYC Collegeline.

Unlike the lower level classes, there are fewer students in ESL 7. I count 15 seated comfortably at four round tables, with Newburyhouse dictionaries stacked in the center of each. With their eyes glued to the Lenovo laptops in front of them, the college-bound students talk softly among one another. Meanwhile, Ms. Devore moves from pupil to pupil, helping each of them decide on a scholarship for which to apply. For the past few weeks, Ms. Devore’s class had been drafting and developing their end-of-the-semester essays, to be used for grant money applications too. Now, the students’ assignment is to decide by the end of class on a scholarship to target.

When Ms. Devore notices that many of her students have clicked on sponsors and foundations that do not require the submission of an essay, she advises them to look elsewhere—which seems like smart advice to me, since scholarships that do not require essays are likely to receive a higher number of applicants, hence more competition.

Despite his teacher’s recommendation, I hear Johnny remark to the two girls next to him in Chinese, “Just pick some and apply to them,” as to quickly wrap up the day’s task. His happy-go-lucky attitude and eagerness to chat strikes me as a quality that is uncommon among most of the students I have observed and spoken to at the high school.

“In China, I was not really interested in studying, so I would play a lot . . . so when I came to America, I still wanted to play and I wanted to make and save some money to start my own business.” Johnny began his days in the United States washing dishes and bussing tables at Chinese restaurants in various places like upstate New York and Vermont, away from his parents in the city. Instead, he lived in the communal apartments that his bosses owned and rented out to workers like him.

After two years, he realized how strenuous restaurant life could be. He said he made good money working six days of the week for about 14 hours every day, but it was monotonous. No one around was his age so he spent a lot of time talking to himself, said Johnny, laughing.

“At that time, my English was not very good, and I didn’t have a driver’s license, so I would go to the restaurant, back to the apartment, go the restaurant, and back to the apartment.” On his day off, he would stay inside and maybe order a pizza. That’s when he decided to go back to school and enrolled in to Lower East Side Prep.

“As I said before, I want to have my own business, so I have to learn more English,” he said. In less than two years, he has become one of the school’s best students in English, in part because of his past gigs as a waiter in locales with small or non-existent Chinese enclaves.

“I watch movies and learn from the movies how to pronounce. I’m not sure if that works for everybody,” he said. More than anything, it’s his fearlessness and unconcern with saying something wrong. “I’m not afraid to speak English with Chinese people. They're afraid to speak English with me,” he said. “It is a problem.” But it may be one that stems from the students’ cultural tendency to be studious yet also quiet and reserved, Ms. Polin explained. Fortunately, there are those like Johnny whose outgoing personalities and eagerness to converse have helped them succeed in school.

“ . . . Every year I have a couple of kids that knock on my door and say 'Can I come in and talk to you?’ And I’m like, ‘About what?’ And they say 'About anything . . . ’” the principal recalled, echoing their very words. Students would come to talk to her about virtually anything simply to practice their English.

One of the students who would stop by her office is now an IT worker at Goldman Sachs, who first came to Lower East Side Prep not speaking a word of English, Ms. Polin said. After about a year and a half, however, the student was speaking as well as a native speaker. “ . . . When I talked to him, I said, 'Why is your English better than everyone else’s?’”

Turns out that the student, just like Johnny, would study and repeat the English words he heard on American television and radio. Although it’s a tedious, long process that takes a lot of patience, it’s one that has worked. Ultimately, these success stories are what inspires teachers like Ms. Devore.

"The students here are really motivating to me,” she said. “I see how hard they work, and a lot of it is hard—yet they persist. It's not just academically hard. They're thrown into learning in a new way at a time when they're trying to survive, to navigate the culture—they're trying to navigate the language.”