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Reintegration Roadblocks

Previously incarcerated Connecticut residents face complicated barriers to receiving their licenses, making it difficult to get work.

Design by Kevin Chen.

Jimmy Robinson is learning how to use the Uber app in Claire’s Corner Copia. Dressed in a newsboy cap, a pink jacket, and a plaid button-down, he looks at his phone skeptically. His friend Annie Nisenson managed to secure him a $100 voucher for the app, and she leans over his shoulder to show him how to navigate it. Apps like Uber are new to Robinson; in fact, most are new to him. Robinson was serving life without parole before an unexpected pardon culminated with his release in 2021. He recalls the length of his incarceration exactly: forty years, seven months and two hours.  

Robinson is used to taking the bus to work each morning. His bus is supposed to come at ten minutes to six. Sometimes the bus comes early, sometimes late, Robinson says. But he tries to make it to the bus stop at a good time for him to arrive at work on time no matter what—he works at EMERGE, an organization that supports clients through a variety of reintegration programs post-incarceration, as a shop manager. 

Instead of using tools like the CT Transit app to support him in navigating the bus system, he has learned by memorization and trial-and-error. He knows the phone number to call about bus status, and does so when necessary. 

Robinson, however, will soon have no need for the Uber or CT Transit app. In October 2022, he was able to secure his learner’s permit. He’s preparing for his road test so he can finally receive his license. 

His license will be a badge of honor, an accomplishment that many people in the process of reintegration struggle to acquire. Connecticut’s most recently available data from the National Institute of Corrections suggests that as of December 31, 2019, 36,475 residents are on probation and 3,651 are under parole. For most of these residents, transportation––everything from navigating public transport to securing a license––is a major barrier to reintegration.

On top of the burden of finding a job is finding one accessible through public transportation. With no car and no flexible income to afford ride-share apps or taxis, formerly incarcerated people depend on buses, trains, bicycles, or walking to get to and from work.


When Andrew Ramsay began his sentence, it was 1991. When he came back home, it was 2021.

Since returning, Ramsay has had to learn how to navigate public transportation in New Haven. Ramsay noted that his family has helped him, but that he initially depended on Uber so as not to “disrupt” their lives. He stopped using Uber because the app’s surge pricing left a dent in his paychecks. Currently, he switches between public transportation and having a friend drive him.

“Everything is all brand new, so it’s like I’m a baby. I’m starting all over again,” Ramsay says. He speaks eloquently about the difficult process of securing the required documents to acquire a license, emphasizing that he keeps faith and patience.

Like Robinson, he is employed at EMERGE, a self-described “self-sufficient social enterprise committed to assisting formerly incarcerated people successfully integrate back into their families and communities.” They have a variety of programs for formerly incarcerated people to get started, including a Transitional Employment Program, peer-to-peer group meetings called Real Talk, and a Trauma Informed Men’s Group. In their Transitional Employment Program, participants earn at least $15 an hour, while working up to twenty-four hours a week in construction, landscaping, and property management. The other sixteen hours of the work week are reserved for support programs. 

There are six supervisors at EMERGE, all of whom have been through EMERGE’s programs and have experience being formerly incarcerated. EMERGE Executive Director Alden Woodcock calls them “the heart and soul of the organization,” noting their roles teaching crewmembers, communicating with staff, operating equipment, and caring for the organization’s tools, vehicles, and equipment. 

In the mornings, participants arrive at EMERGE’s headquarters at 830 Grand Avenue—on a bus line—and from there they split up and drive to different worksites or work from the headquarters. EMERGE supports their participants throughout the process of securing documents, bus passes, and licenses. They helped Ramsay get a bus pass and Robinson secure his permit.

Ramsay found out about EMERGE at a job fair. There were construction hats lined up on a table and some people in discussion around it. He walked over and started up a conversation. “They heard my story and wanted to see better for me and I’ve been there ever since,” Ramsays says. “Everything that I need to really navigate in society EMERGE has helped me to get.” 

Ramsay is now one of the supervisors at EMERGE, many of whom drive newer employees to their job assignments.––Supervisors that cannot drive stay at the EMERGE building or support in other ways instead. Ramsay sometimes feels “discouraged” because he cannot help the team by driving. 

Currently, Ramsay is working on securing his Social Security card in order to apply for a state identification card, and eventually a driver’s license.

Ramsay wakes up around 4 a.m. and starts his day with a prayer before getting ready. By 6 a.m., he’s off on the ten-minute walk from his West Haven home to the bus stop. He leaves the house early to give himself time in case the bus is early. Ramsay takes the 265 to the New Haven Green, a ten to fifteen minute ride, and then walks another thirteen minutes to EMERGE’s headquarters. He is a supervisor now, and makes sure to be there before 7 a.m. The total commute takes about forty five minutes.

If Ramsay had a car, the commute would be about fifteen minutes. But in the year since he was released from incarceration, he has been unable to secure a state identification, or a driver’s license. 

“I pay my taxes. I’m working. I’m doing all these things. And to this day, I’m still struggling right now to get my documentation,” Ramsay says. This documentation is not just essential for transportation—identification is often required to apply for housing, banking, and healthcare.


It can be incredibly difficult to get a job post-incarceration, especially with the increase in national unemployment since the start of the COVID-19 pandemic, not to mention the usual obstacles for formerly-incarcerated people – employer prejudice, lack of educational degrees, and a lack of the documentation necessary to be added to someone’s payroll, for example.

The court’s expectation for formerly incarcerated people is to integrate immediately, requiring weekly proof of job searches to be sent to their probation officers, noted Hannah Duncan, the Curtis-Liman fellow at Yale Law School’s Arthur Liman Center for Public Interest Law. This creates pressure to accept any offer at all––even if the job is far away or has odd hours. Duncan herself has managed clients who commute for hours to get to and from their job.

In the federal system, supervised release or probation can be part of a sentence, and those under these must still report to a probation officer. Violating conditions of their release from custody as part of their probation or supervised release can mean you get sent back to jail––full-time employment is often a condition of release from custody, Duncan says. Full-time employment being a condition often leads to accepting the first job offer you get. On top of this, it is immensely frowned upon to reject offers in the face of so many job application rejections. 

On top of the burden of finding a job is finding one accessible through public transportation. With no car and no flexible income to afford ride-share apps or taxis, formerly incarcerated people depend on buses, trains, bicycles, or walking to get to and from work. 

The New Haven bus system is run by the Connecticut Department of Transportation, and is free to ride for now, as the state legislature recently extended a free bus policy until April. Ramsay describes the bus system as “O.K..” The buses can be inconsistent, so he opts for the walk from the New Haven Green to EMERGE.

Unless people get jobs on a bus line, they need a car. But, for the formerly incarcerated, getting a car is painfully difficult.


The majority of Connecticut residents––more than three fourths––drive alone to work, but formerly incarcerated people struggle not only to secure a car, but also a permit, license, and registration. 

Much of this struggle boils down to the same thing: applicants need documents that people who have been away from home for prolonged periods of time tend not to have. And they cost money to get.

In order to secure an identification from the state of Connecticut, applicants must show three categories of documents: proof of identity, proof of a Social Security number, and proof of Connecticut residency. 

Proof of identity should include at least one “primary document.” For U.S.-born citizens, “primary documents” must be a birth certificate or a passport. 

Alden Woodcock, EMERGE’s Executive Director, notes that unless a family member saves your Social Security card and birth certificate for you while incarcerated, it is incredibly difficult to secure a state-issued identification card. According to Connecticut 211, a human and social services resource, personal documents obtained during intake or incarceration are stored in “a secure location” at each correctional facility.

Nonetheless, Robinson notes that there is a lot of “poor management” and that his Social Security card was lost during his incarceration. 

Even if a family member is able to hold onto your documents, this might not be enough, depending on the length of the sentence. Illness, death, and other unprecedented factors can affect whether family or friends have been able to hold onto them––the longer the sentence, the older parents and family members get and the more likely illness or death has affected them.

For Ramsay, who is a U.S. citizen but was born in Jamaica, the process of securing a birth certificate was even harder. His mother formerly had his documentation, but she passed away during his sentence and his documents were lost. Ramsay has been making lots of phone calls and sending lots of emails to gather the documents he needs to prove that he is a U.S. citizen.

“I pay my taxes. I’m working. I’m doing all these things. And to this day, I’m still struggling right now to get my documentation,” Ramsay says. This documentation is not just essential for transportation––identification is often required to apply for housing, banking, and healthcare.

To request a birth certificate, applicants must go to the town vital records where they were born, the town of their mother’s residence at the time of birth, or the State Vital Records Office. In order to request it, they must fill out an application and mail it, along with a government-issued photo identification, and a payment of $30 per copy. 

In Ramsay’s case, he had to contact the Jamaican government and pay for his birth certificate to be sent to Connecticut. So far, this is all he has been able to secure in order to demonstrate proof of identity and citizenship, but is still in need of his Social Security Card. 

Alongside a birth certificate as primary documentation, you can show a passport at the DMV. Similar problems occur with this option––passports, which expire ten years after being issued, are no longer valid for many leaving incarceration. And to apply for one, applicants must show a birth certificate, proof of identity, and pay the required fees (which consist of a $130 application fee and a $35 “execution fee”).

To get both these pieces of identification, you run into circularities and dead ends. If applicants want to recall a birth certificate, they need an identification. If they want an identification card, they need a birth certificate. But what are applicants meant to do when they are starting over?

The second category of documentation that applicants are required to show at the DMV is proof of Social Security. This can be in the form of a Social Security card, or specific tax forms. Tax forms, however, require consistent employment that not all formerly incarcerated people have. They are also usually given to employees in January to denote the payments of the year before; depending on when they begin work, this could leave applicants up to a year with no identification. 

Ramsay still has his Social Security number, but this is not enough for the DMV––they want the physical card. This can be another dead end: in order to request a Social Security card replacement from the Social Security Administration, applicants are asked to show a driver’s license. It’s circular. 

Ramsay has been unable to acquire his Social Security card so far. Robinson notes that the pandemic made it more difficult to secure his own card, as he had to make routine calls to explain his situation instead of going to the offices directly and receiving guidance.

For proof of residency, there must be two pieces of mail from two separate senders. This means that people experiencing housing insecurity face additional barriers.

Ramsay is still fighting to get his identification and Social Security card; he has depended on EMERGE’s assistance throughout the process. He gets little help from his probation officer. The State of Connecticut’s Judicial Branch defines the role of probation officers as responsible for providing “intake, assessment, referral, and supervision services to [the] sentenced individual.” This notably includes check-ins to ensure that probationers are making progress in their re-integration. Despite this, Ramsay’s probation officer has told Ramsay that securing his documentation is not within the scope of their work, emphasizing to Ramsay that the officer’s role is to come to Ramsay’s house or office, take urinalyses, and make sure he has a job.  

“It’s easy to say ‘You know what? Eff this.’ and go back to what we know,” Ramsay says. “And that’s where the problem comes in…You go through a lot of hurdles, but I just try to stay faithful.”

To secure a license, they have to navigate the multitude of documents and applications to secure their documentation, pay all the required costs, acclimate to life post-incarceration, abide by their probation officer’s requirements, and work towards financial stability in the process. If all of this sounds confusing, that’s because it is. 

There are barriers for people post-incarceration who’ve held driver’s licenses in the past, too:  incarceration usually implies driver’s license suspension. In order to retain the license, there is a required restoration fee of $175. If there are taxes owed on a vehicle under the applicant’s name, then the taxes or tickets must be paid off, too, before the driver’s license can be restored. 

To get both these pieces of identification, you run into circularities and dead ends. If applicants want to recall a birth certificate, they need an identification. If they want an identification card, they need a birth certificate. But what are applicants meant to do when they are starting over?

Once those are all paid, driving privileges are restored, meaning it becomes possible to apply for a learner’s permit. Even if someone has formerly held a license, they are required to re-acquire a permit, with the restriction that the holder can only drive when accompanied by someone twenty years or older who has held a license without suspension for more than four consecutive years. After ninety days with a permit, applications must pass a vision test and a twenty-five-question knowledge test, and take an eight-hour Safe Driving Practices Course. Failure of the vision or knowledge tests require applicants to reschedule the tests online and pay the fees once again. These include a $40 testing fee (that includes all the tests) and a $19 fee for the learner’s permit itself. The fee for a non-driver state identification is $28. This process can be long and expensive.

Not only are the abundance of fees a barrier to many, testees need to provide their own vehicle for the driver’s exam and potentially miss work for the permit test, Safe Driving Practices Course, and driver’s test. Availability for appointments range from 7 a.m. to 6 p.m. on weekdays, with some available slots on Saturdays.  

Robinson had to wait almost a year to get his Social Security card. His documentation was lost during his sentence, although he is not sure why. Through work with the Parole Project in Louisiana, where he was incarcerated, and EMERGE in New Haven, he has managed to secure his Social Security card, birth certificate, and, as of October, his learner’s permit. Following his release, Robinson moved to New Haven to support his mother, with whom he currently lives. He notes that securing a Social Security card was particularly difficult as a result of the pandemic, since he could not go to the offices and work out what was necessary. Instead, he fielded calls and emails until he was able to secure it.

Robinson had to return on three separate occasions to the DMV before they granted him a learner’s permit. Once, they refused him because the letter he showed did not have a date on it.

“You see so many people,” Robinson says. “They become heartbroken because they go to get their license and many fail time and time again. And it’s like it’s very next door to being impossible.”

In total, fees can amount to about $348, including testing, document copies, restoration fees, and the combined cost of securing both a permit and license. Applicants also have to pay the fees for each attempt if they fail, a burden for those with inconsistent or low-paying work.

“Those are barriers that you have to go through, but you got to go through them because you’re trying to dismiss catching the bus and being to work on time,” Robinson says. “You don’t have a lot of support. You don’t have a lot of help…Just trial and error, you know, that’s how you learn the system.”

Robinson finally secured his permit on October 10, 2022, about a year after his release. 

“It’s wonderful,” Robinson says. “I’ve gotten a job and through EMERGE and been promoted from a crew member to a shop manager. Now I’m real close to getting my driver’s license… And I’m not the only one.” 


Design by Kevin Chen.

As a result of this long and difficult process, many people reintegrating post-incarceration drive without a license, according to Liman Fellow and lawyer Hannah Duncan. Throughout her work in public interest law, she has been informed of cases where individuals violate parole, probation, or supervised release in order to drive out of necessity.

“It’s just so much easier,” Woodcock, EMERGE’s Executive Director, says. “Your chances of being pulled over are pretty slim, but if you do get pulled over without a license, and you’re on parole, you can get violated and sent back to jail. So that’s the risk that you run.” 

The problem does not end once a license is secured. Now comes the process of buying and registering a car.

Getting a car alone is a costly process. In the last two years, used-car prices have increased dramatically––used car prices are currently 43 percent higher nationally than the typical depreciation rates. Additionally, securing a loan to pay for a car is significantly harder for someone with both a criminal history and little to no credit history. 

In order to register a car, identification in the form of a driver’s license or passport must be provided, along with proof of ownership in the form of a title or former owner registration. If the vehicle is from another state, there are different requirements.

“You see so many people,” Robinson says. “They become heartbroken because they go to get their license and many fail time and time again. And it’s like it’s very next door to being impossible.”

The DMV also requires proof of Connecticut car insurance and a Bill of Sale, a document with vehicle, buyer, and seller information, as well as the selling price and date of the vehicle. These can be drafted independently as long as they include all the necessary information. Car insurance in Connecticut can cost upwards of $800 per car, but drivers with a driving record or violation are charged more––sometimes upwards of $2,000. Despite car insurance being mandatory in most states, companies can still deny applicants due to many factors, including credit history, type of vehicle, financial history and driving record.

The DMV charges fees for car registration, in addition to the insurance required for registration. To register a regular passenger car, the fees total $225. 

Ramsay notes that a license may seem like “a small thing, but it’s a big thing at the end of the day.” He echoes that the difficulty of the process can be inhibiting to many who are trying to reintegrate. 

While only 10 percent of Connecticut residents are Black and 15 percent are Hispanic, 40 percent of incarcerated people in Connecticut are Black and 25 percent of them are Hispanic. As a result, these re-entry costs largely impact people of color disproportionately. 

Things like state identifications and driver’s licenses are determined by state and federal requirements, meaning local government has little bearing on these requirements. New Haven’s main contribution to people reintegrating is through workarounds to getting a driver’s license: the public transit system and continued development of bike lanes. In summer of 2022, New Haven announced its Safe Routes for All Plan, which hopes to move away from a city transportation system that is based around cars, by enhancing the infrastructure of biking, walking, and public transit in the city. 

Woodcock, EMERGE’s Executive Director, notes that most formerly incarcerated people he is aware of through EMERGE take public transportation or depend on others for car rides, while a smaller amount bike or walk. 

Ramsay continues to gather the necessary documents to get his permit soon. Robinson will soon be scheduling his first attempt at his road test since passing the written test for a driver’s license.

“If you don’t have this documentation, [it’s easy to] go back to what you know,” Ramsay says. “But that wasn’t my case. I said, ‘You know what? I’m just gonna still take it one day at a time.’”

Ángela S. Pérez Aguilar is a junior in Berkeley College. 

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