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Massachusetts education Commissioner Jeffrey Riley is recommending probation for a Roxbury charter school in the wake of shrinking enrollment, declining student achievement, and financial problems — a high stakes move that could eventually lead to the school’s closure.

City on a Hill Charter School, which serves about 400 students in grades 9-12 in two locations, will have two years to turn around its operations or it could be closed, under the recommendation. The state Board of Elementary and Secondary Education is slated to vote on probation next Tuesday as part of renewing the school’s five-year operating license.

“Our concerns about the school’s fiscal viability, lack of demand, and poor academic performance warrant placing the school on probation with conditions,” Riley wrote in a memo last Friday to the board. “I am not, however, recommending nonrenewal [of the operating license] at this time because the school has proposed major changes to address these deficiencies, appointed a principal with a track record of academic success, and taken action this year in an effort to yield better results for students and families.”

The state’s action represents the latest turbulent twist for the 25-year-old charter school. Once a shining star in the Boston charter school world, City on a Hill has run into wide-ranging problems in recent years as it attempted to expand its charter school into a small network of schools, opening a second location in Roxbury in 2013 and another school in New Bedford in 2014.

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But in the end, officials failed to replicate the success. They also experienced deteriorating academic achievement at its original school, while state officials last year placed the New Bedford site on probation. In November, charter leaders took dramatic steps to stabilize their operations — as state officials were weighing whether to renew their operating license in Boston — announcing they would close their New Bedford location in June and consolidate the two Roxbury schools. The plan called for laying off about two dozen teachers, administrators, and other staffers.

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Kevin Taylor, who became the school’s chief executive officer in July 2018, called the commissioner’s recommendation for probation unfortunate, but added it was not unexpected. He vowed the school would turn around both its finances and academic programs and was glad that the commissioner supported their plan to downsize to a single school again.

“This has been a very challenging time for families, staff, and administration,” Taylor said in an interview. “I do believe our best days are still ahead of us. I have great hope that the steps we are taking will result in us being the premiere stand-alone high school charter option in the city.”

A state review conducted as part of the licensing-renewal process for the original Roxbury school describes a charter school network in deep turmoil as it has confronted years of unstable leadership at the highest levels. In the past three years alone, 20 trustees have left the board, while the overall number of board members has dwindled from 15 to eight. And since 2014, the charter network has had four different chief executives.

During that time, frustrated teachers unionized, a rare action at charter schools, which place a premium on operational flexibility, but have experienced difficulty in securing contracts with trustees.

The review, according to Riley’s memo, found the school has drifted considerably from its mission of preparing students for the 21st century and is no longer carrying out its college preparatory programs. In visiting the school, state reviewers “found a lack of high expectations for all students, a lack of student engagement, and evidence that classroom environments were not always respectful or conducive to learning,” Riley noted.

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While City on a Hill once boasted waiting lists of nearly 500 students, officials are now struggling to fill seats. Just this fall, 15 percent of students opted not to return, and many students who secured seats in lotteries decided not to take them. Currently, the two Roxbury sites are collectively underenrolled by about 140 students, according to state data.

The shortage of students comes at a big financial cost to the charter school, which receives about $20,000 per student in state aid that is redirected from the City of Boston. Finances are so bad, according to Riley’s memo, that the Roxbury schools and their foundation defaulted on a multimillion-dollar loan and in November entered into a forbearance agreement with the lender. Consequently, the foundation no longer can allocate funds to the schools until certain conditions are met in that agreement.

Taylor emphasized on Thursday that City on a Hill has made all loan payments but failed to have enough cash on hand for the expenses it had — as required in the covenant for the loan.

“The default on the covenant is directly tied to the lower student enrollment,” he said.

If the state board approves the commissioner’s recommendation, City on a Hill will officially consolidate this summer into a single school in Roxbury at its Circuit Street site, which it owns. Enrollment will initially be capped at 350 students, and if performance improves it can expand to 400. To fit into the Circuit Street site, Taylor said, the school will eventually need an addition, but added the school prefers a single site.

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Dalles Smith said he’s glad that his son will be graduating from City on a Hill in June, noting it’s been a chaotic year. He said the school was too ambitious with its expansion, and it never made sense to have two separate schools less than a mile apart. In recent months, the two schools have been sharing staff.

“You can’t have a guidance counselor, teachers, and principal running back and forth between two schools,” he said.


James Vaznis can be reached at james.vaznis@globe.com. Follow him on Twitter @globevaznis.