As director of the National Consumer Law Center’s Student Loan Borrower Assistance Project, Persis Yu spends her days doing pretty much exactly what her title implies — working on behalf of low-income student loan borrowers both helping them with their individual cases and advocating for laws and policies that would benefit them.

But for about six months last year, Yu found herself in a strange position: Advocating for herself as she worked to manage her own student loans.

Yu faced delays of several months as she tried to switch from one program that allowed her to pay her loans according to her income to a different income-driven plan. For a short period, her loans actually flipped into delinquency, a status which means you’ve missed a payment, because her servicer — the company the government hired to manage her federal student loans — took too long to apply a payment pause, known as an administrative forbearance, she was entitled to by law as she went through the application process.

“It was absolutely ridiculous the amount of resources and the expertise that went into getting my loans,” switched from one repayment program to another, Yu said.

Persis Yu and her son. Persis Yu

Her experience underscores the challenges faced by the 44 million student loan borrowers across the country as they navigate the repayment process. The complexity of the student loan system, which includes both federal and private loans, a myriad of repayment programs with varying risks and benefits and severe consequences for mistakes, has left many student loan borrowers confused. Even more troubling, difficulty navigating the student loan repayment process often puts borrowers at risk of financial strain, according to a slew of government reports.

Yu knows all of the finer points of student loan law and has had the ear of some of the country’s top policy makers on this issue, and yet she still had trouble getting the system to work for her. What’s more, she’s not alone; MarketWatch spoke to half a dozen student loan advocates and policy experts about the challenges they’ve faced navigating the loan repayment process. And if even they are struggling, where does that leave the rest of us?

“If the people who are literally in the room writing the regulations can’t get it to work for them, how can a borrower, who is just trying to wade through the myriad of options?” Yu said.

Policy expert waits months to access repayment plan she helped design

In late 2015, Jennifer Wang, the director of the Washington, D.C. office of The Institute for College Access and Success, a nonprofit focused on higher education equity, was looking forward to finally getting the chance to take advantage of a new federal student loan repayment plan — known as REPAYE — that she’d helped develop with regulators and other stakeholders. But the experience turned from “really cool” to “extremely frustrating” after several months of waiting for her servicer to process her application.

Wang applied to switch to REPAYE on the first day the application became available, Dec. 17, 2015. She received no communication acknowledging the application until Feb. 2, 2016 when she got an email from her servicer instructing her to log into her account to view a letter indicating her application was approved. When she logged in, the letter wasn’t there and it took multiple calls to customer service and three more months to get the situation sorted out. In the meantime, her student loan servicer auto-debited her bank account multiple times for her old, higher repayment amount.

Jennifer Wang (left), the director of the Washington, D.C. office of The Institute for College Access and Success, spent months trying to get into a repayment program she helped design. Courtesy of Jennifer Wang

Wang said she advocated for herself throughout the process because she had a thorough understanding of what her student loan servicer was required to provide her under the law. “If I didn’t know anything about how servicers aren’t supposed to leave you hanging, I probably would have assumed this was normal and not followed up,” she said.

A student-loan attorney struggles with his own auto-debit

It was the experience of navigating the complex process for repaying his own student loans with little help that inspired Boston attorney Adam Minsky to specialize in student loan issues. “It was clear to me that if I’m struggling with this, a lot of other people are going to be struggling with it,” he said.

Even since he began practicing student loan law about six years ago, Minsky has still faced challenges with his own loans. He’s had trouble with auto debit and recertifying his income so he can stay on his payment plan — problems typical of other borrowers, according to advocates and reports from the Consumer Financial Protection Bureau. “I know what I’m doing, I know what the steps are and I’m still encountering problems. That tells me that the system is pretty messed up.”

Student loan servicers often blamed for the confusion

Advocates tend to put much of the blame for the confusion on student loan servicers. Reports from the Government Accountability Office, the CFPB and probes from state law-enforcement officials indicate that these companies often don’t provide borrowers with enough or the right information to successfully manage their debts. Borrower advocates have also criticized government officials for doing little to incentivize servicers to work in borrowers’ best interests, failing to hold the companies accountable and making the process of paying back student loans overly complicated.

In recent months, they and Democratic lawmakers have expressed concern that Secretary of Education Betsy DeVos is taking steps that would make it easier for servicers with a poor track record of working with borrowers to keep lucrative government contracts.

For their part, servicers argue that much of the difficulty borrowers face is a result of an overly confusing system with too many options. What’s more, borrowers compound their challenges by not reaching out to their servicers for help, the companies say.

But in a telling exchange with representatives from a student loan company during a Maryland General Assembly hearing earlier this year, a state lawmaker described the challenges he faced getting answers to basic questions from his servicer about his family’s student loans, like who is actually servicing them. Ultimately a staffer from the student loan company, who was part of the hearing on proposed legislation to regulate student loan servicers in the state, offered to give the lawmaker his business card to help him sort through the confusion.

Student Debt Crisis director missed an important loan deadline

For Cody Hounanian, confusion created by his servicer has cost him thousands of dollars. As the program director at Student Debt Crisis, a Los Angeles-based nonprofit working on higher education issues, Hounanian is steeped in the challenges borrowers face paying back their loans and he’s often involved in putting on how-to webinars and other programs for borrowers navigating the student loan system. And yet, he missed an important deadline that caused the balance of his loans to jump.

Two years ago, Hounanian went about the process of recertifying his income so he could stay on his income-driven repayment program. His servicer communicated two different deadlines for doing this in two different places and so he missed the deadline. The consequence: He was pushed back into the standard repayment program, which doubled his monthly payments until he was able to get back into the income-driven plan and added $2,000 to his loan balance in the form of capitalized interest.

“That was a good wake-up call for me,” he said. “That made me realize that even the most responsible, diligent and aware student loan borrowers can slip up and it can cost them.”

Public service loan forgiveness is a gray area

But it’s not just servicers that create confusion for borrowers, it’s also the design of some of the programs, Hounanian said. When he first began working at Student Debt Crisis, he figured he’d be able to access the Public Service Loan Forgiveness program (PSLF), an initiative that allows federal student loan borrowers to have their debts wiped away after 10 years of payments if they work for the government or a nonprofit. He very quickly realized that because he worked for a 501(c)4, he likely wouldn’t qualify for the program.

“The work I do, I consider to be an important public service,” he said.

Rachel Fishman, a senior policy analyst with the Education Policy program at think tank New America, has been working for months to get some of her loans certified for a forgiveness program. Courtesy of New America

That conundrum has received more attention in recent months as a lawsuit filed by the American Bar Association accusing the government of reneging on promises of loan forgiveness for public servants winds its way through the court system. The PSLF program, which was established in 2007, faces a major test later this year as the first cohort of borrowers looks to claim forgiveness. Experts and advocates have been warning that borrowers who believe they qualify may find themselves disappointed because they don’t have the right type of loan or right type of job.

Senior education policy analyst on a constant paper-chase

The several months Rachel Fishman, a senior policy analyst with the Education Policy program at think tank New America, has spent sorting through her documentation for PSLF has left her feeling concerned about how borrowers without her expertise will navigate it. Borrowers can keep track of their progress toward forgiveness by submitting what’s called an Employer Certification Form (ECF) documenting their payment and employment history. Fishman has been asked more than once to submit additional documentation proving one of her employers qualifies for the program.

She’s confident the organization falls under the purview of the program, so she plans to keep sorting through the process, no matter the hassle. But Fishman says she wonders how a typical borrower would handle the repeated back and forth and requests to track down obscure paperwork.

Wang describes her and her fellow advocates’ expertise in the intricacies of student loan policy as a “huge privilege,” given the havoc that challenges with student loans can wreak on your financial life. But, she added, not everyone will have that kind of help.

“We do have a clearer picture of what is supposed to happen to borrowers,” she said. But,” she added, “it’s still a struggle for us and I do get confused,” she said.