Dominican-native Yilbert Pena used to divide his life into two halves. The first half was the blithe era until his 16th birthday. That day he went to his mother asking for the papers he needed for his drivers permit application and discovered he possessed none of them. Pena is a burly, affable presence and quick to smile, but he offers a gloomy analogy to describe learning of his undocumented status. “It’s like suddenly becoming handicapped,” he says. “Everyone around you is doing stuff you can’t.” Seeing no benefit in earning a high school diploma if he was barred from jobs that demanded one, Pena dropped out. He fathered a child. Paranoid about being deported to an island country he had left when he was eight years old, he hid his status from everyone he knew, including the mother of his daughter.

On June 15, 2012, though, Pena saw a glimmer of a radically different life. President Obama–whom Pena had been phone banking for in anticipation of the November election–announced he was going to suspend deportations of the so-called DREAMers. These were, in the president’s words, people who came to this country as children, and “often have no idea that they’re undocumented until they apply for a job or a driver’s license or a college scholarship.” He was describing Pena’s situation, and the just-turned 19-year-old remembers excitedly hugging his girlfriend as they watched the television clips and then phoning his mother to share the news. “This,” he told himself, “could change everything.”

There is one thing Pena wishes the president had added in his Rose Garden statement, though: a directive to DREAMers to go out and acquire documentation showing they were in the United States. Because when the regulations for the Deferred Action for Adult Children (DACA) program were published, it turned out that applicants not only had to meet an age requirement (16 and under when they had arrived, and no older than 30 when the change was announced) and provide proof of residency for the past five years, but also had to demonstrate they had been here when the President had unfurled the new policy. And Pena, who had been so careful not to leave footprints, didn’t have any receipts or bills to show that on June 15th he was living in New York, the city he’d called home for most of his life.

It’s a problem many of the older DACA-eligible crowd–the ones who have left or graduated from high school years ago–are encountering. “For applicants who don’t have current school transcripts and who have been told for years to hide their presence for their own safety, it can be challenging to prove they were here,” says Dan Berger, a partner in the Northampton, Mass.-immigration law firm Curran & Berger. “Pulling together their applications takes creativity and detective work.” Deeds or mortgages, tax receipts, dated bank transactions, pay stubs, and utility bills–basically, the evidence the Department of Homeland Security recommends submitting–tend not to be part of an undocumented immigrant’s life. It’s an issue that could plague millions of immigrants if broader reform does indeed pass. If the experience of the DACA cohort is a good indication, when these men and women have come into contact with Official America, it was often unintentionally.

That’s made for some ironic situations. Immigrants who have committed infractions that fall short of a felony can find their brush with the law turns out to be the key piece of evidence for their DACA application. “It’s always a strange conversation when you tell your client that, ‘yes, you should definitely apply despite the speeding ticket, and as a matter of fact we’re going to submit it to the federal government,” says Laura Lichter president of the American Immigration Lawyers Association. “A lot of immigration law is quite frankly back asswards.”

Gail Thalmann, a retired teacher who lives on Long Island, about an hour and a half away from Pena, has helped several of her former students through their DACA applications. A Salvadoran kid who graduated in 2011 and then worked off of the books for an auto repair shop had a very difficult time proving he’d been in the country after he’d left school. The Department of Homeland Security returned his application with a request for more evidence. Then there is the boy whom Thalmann–who asked to be referred to by her maiden name, because she’s known for working with a group of Latino kids and doesn’t want to draw attention to their undocumented status–affectionately refers to as the “careless one.” He had no trouble pulling together his application: for 2012, he had a driving without a license ticket and for the June 15th date he could submit the hospitalization record he had acquired after nearly cutting off his finger with a hedge trimmer. “It’s the kind of stuff I wouldn’t want on my record,” she says. “But given the circumstances, I’m glad it’s on his.”

Pena, unfortunately, ended up in a position similar to that of the squeaky-clean ex-student. Most of his documents were from school: In addition to report cards, there was a letter the administration had sent to his home warning he was in danger of flunking gym. After he dropped out and started working in construction, the rest of his papers came from situations where acquiring documentation wasn’t a matter of choice. His daughter’s birth certificate attested that Pena had been present at Jacobi Medical Center in the Bronx on December 29, 2010. His closest friend, a Marine, had sent Pena a letter from Parris Island, S.C. while he was in boot camp; that proved Pena was in the country in early 2012. The elusive piece of evidence was for June. He couldn’t think of anything that could suffice.

Pena had racked up receipts that day; they just weren’t in his name. He’d made several calls on his cell phone, but the H2O prepaid plan was under the name of his stepfather, who is a legal resident. Pena had used a debit card to take money out before he’d boarded a bus to Orchard Beach in the Bronx, but it was also under his stepdad’s name. What frustrated Pena most was that his boss had urged him to open a bank account; instead Pena had stashed cash in a safe he’d bought at Home Depot that looked like an Ajax cleaner so it wouldn’t stand out among his cleaning supplies. “I was just scared to put my name on anything,” he explains. That had seemed prudent. Now it was keeping him from the program that would have allowed him to restart a life that had seemed halted for three years.

The only evidence that tangentially placed Pena in New York on June 15th was Facebook. His profile page listed him as a resident of the Bronx, and he’d posted some pictures of himself in June. While it was an unorthodox choice for submission as part of a federal application, many DREAMers had sent in posts to prove residency. But Pena’s posts didn’t include an identifiable landmark, and in any case, Jessica Greenberg, an attorney at the African Services Committee in Harlem who took on Pena’s case, was wary of resorting to social media. Posts could be altered, which the federal government was, of course, aware of.

Plus, the standards for the June 15th evidence were higher than the rest of the application. The Department of Homeland Security was accepting affidavits, or letters, from people like employers, clergy, and former teachers attesting that the applicant had worked for them, or attended their church, or sat in their classroom in the States. But the government was not accepting affidavits for the June 15thdate, to insure that immigrants who had left the country before the change in policy wouldn’t return to take advantage of the new opportunity. So even though Pena’s boss had offered to write him a letter, it wouldn’t do him any good.

The fact that an escape from Pena’s undocumented netherworld had materialized, and yet remained inaccessible was, in his words, “crazy making.” It had never been easy to get through his days doing non-union construction jobs, but after he reached an impasse on his DACA application it became more painful. “You have this feeling that your life is never going anywhere,” he says, “even when you’re working seven days week and working really hard.” Pena would get texts in the evening summoning him to a site at 5 AM the next morning; then, for 12 to 14 hours he would carry 80 pounds of concrete on his back and stir cement under a hot sun. At one point he’d seen an out from the job he’d come to loathe: Pena is a self-taught technology whiz and the owner of a rug cleaning company approached him about running IT for the small business. But when the man had discovered Pena didn’t have a social security number, he withdrew the offer.

Greenberg encouraged Pena to keep mulling over his whereabouts around the time of the President’s announcement “Don’t worry about June 15 — look at the month of June,” she wrote him in an email. “Try to recount what you were doing.” Pena racked his brain and kept coming up short. He did, however, take steps so that if he were to find that elusive receipt, he could apply for DACA right away. One of the program requirements for those without a high school diploma is to have a GED or proof that you are working towards one; in January of 2013, he quit construction work and enrolled in GED Plus in the Bronx. Pena wasn’t the only DACA-eligible immigrant who was spurred to resume his education: Enrollment in GED classes skyrocketed to the point where New York City Council Speaker Christine Quinn asked for an additional allocation of $13 million to make sure programs could accommodate the influx of students.

Pena also started compulsively hoarding receipts for documentation purposes, finally opened that bank account, and took out a credit card. It might not make a difference to his DACA application, but if broader immigration reform passed, he wasn’t going to miss out because he lacked some slippery slips of paper.

The bipartisan Senate bill, which was introduced in April, in fact set a lower bar for proving residency than the DACA application demanded. It required just one piece of evidence showing residency before December 31, 2011. Pena wouldn’t have any trouble passing muster. But there was no assurance that the requirement would be part of the bill, or–for that matter–that the bill would become law.

As it turned out, Pena’s fate didn’t hinge on the upcoming Washington debate. After queries from this reporter and Pena, Greenberg reviewed his application again and thought of an unexplored angle. Pena had said he hadn’t been to the doctor, but what about his daughter? He remembered that he had in fact taken her for a checkup on June 18th. “I don’t know where my head was,” he said afterwards. “I just didn’t think of it.” Records corroborated Pena had been present at the pediatrician’s office on nine occasions, including that seminal June date. Just around the time the Senate bill was announced, Pena put his DACA application in the mail, along with the $465 fee.

While his approval hasn’t yet come through, Pena already felt his world expanding. He was on the verge of testing out of the GED program and planned to enroll in community college to become a licensed practical nurse. And then there were the non-professional opportunities that would come with legal residency. He hadn’t been on a plane since he’d come to the United States from the Dominican Republic; he longed to travel there, and see cities like Sao Paolo, which he’d glimpsed in a documentary. “When I get on a plane,” he says, “I honestly think I’m going to cry.”

The DACA program won’t lead to citizenship. It provides temporary work authorization and reprieve from deportation in two-year increments. Signs were, though, that with conservatives like House Whip Rep. Eric Cantor (R-Va.) coming out in favor of the DREAM Act, a version of it would become law, either as a stand-alone bill or as part of comprehensive immigration reform. With his years as an undocumented immigrant appearing to come to a close, Pena regarded the period philosophically. He felt fortunate not just to have met the mix of requirements for DACA, but also for the perspective living in the shadows had provided. “When people say they could never do a minimum wage job at MacDonald’s, that it’s too hard, I think, really?” says Pena. “I’ve seen and done a lot worse. You learn a lot, going through what I went through. You learn how brutal it can be.”