Charles Anderson is a jovial and optimistic high school principal who has hosted events highlighting new Chicago Public Schools’ initiatives, where he offers hugs to the mayor and CPS CEO as they praise the work he is doing at his West Side high school.

At a recent back-to-school fest, Anderson tried his best to sound enthusiastic about the year ahead at Michele Clark High School. But even he admitted to bouts of anxiety. After all, a long shadow of uncertainty looms.

“We are reaching out to every kid that we can,” Anderson said of his disengaged students. “We are going to houses, we are doing events … anything to get kids involved and knowing that it is okay to come back to school.”

Like everyone touched by the city school system, Anderson is contemplating the big questions as the first day of school on Monday approaches.

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How much will the pandemic disrupt in-school learning? Who will be the next CEO? Can CPS re-engage students who dropped off during remote learning?

As CPS begins its new year, these questions and others are what we’ll be keeping an eye on.

Can CPS keep COVID-19 cases at bay?

To do this, the school district will have to administer enough COVID tests to identify exposed students, contact them and get them to quarantine quickly.

But the details of exactly how this will happen, and whether it will work, are among the areas of disagreement with the Chicago Teachers Union, which is trying to negotiate a reopening agreement with the school district.

For example, CPS officials want to limit the number of students who have to quarantine if there is a COVID case in a classroom. It announced earlier this week that only unvaccinated students will have to quarantine. The CTU wants all students to quarantine.

The union is pushing for the same safety standards that were in place during in-person learning last spring while the school district says more relaxed standards, like only quarantining unvaccinated students, are in line with Centers for Disease Control and Prevention recommendations.

The two sides are also debating what remote instruction will look like for students in quarantine. The union doesn’t want teachers to have to simultaneously instruct students at school and those at home without extra support. The union is pushing for classes with students who are quarantining to get substitute teachers.

Though the union doesn’t expect a reopening deal to be reached by Monday, it has said it won’t delay the start of the school year.

As of Tuesday, more than 80 school districts or charter networks nationally have already switched from in-person learning to remote or delayed the start of in-person learning due to outbreaks of COVID-19, according to the Associated Press. In Georgia, after schools got underway, more children across the state were testing positive for the virus than adults, according to the AP.

The head of the Chicago Department of Public Health and CPS’ interim CEO Jose Torres aren’t expecting the same surges in the city’s public schools. For one, masking is mandatory for everyone, whether vaccinated or not.

But given a surging delta variant and the fact that the vast majority of children are ineligible to be vaccinated, it seems inevitable that some students will contract COVID-19. What remains to be seen is how many cases will present, will the school district’s efforts be enough to stop the spread and what will learning look like for students in quarantine.

Who is steering the CPS ship?

CPS has yet to announce its new permanent CEO and that, in addition to the recent resignations of several other top leaders, may add to the sense of unease many are feeling about returning to in-person school while the pandemic continues.

For the last several months, observing the leadership at CPS has been like watching a line of dominos fall. First, CPS’ chief education officer — the No. 2 at CPS—- landed a new job. Then, CEO Janice Jackson followed up later in the spring with an even bigger surprise: She announced she was stepping down from her “dream job.” Jackson did not give a specific reason for her departure, but made it clear the tumult of the pandemic had worn her out.

Mayor Lori Lightfoot fairly quickly tapped Torres to serve as interim CEO, asking him to put his retirement plans on hold. Torres has quietly been trying to get the school system ready for a first day like no other.

CPS had hoped to have a new CEO in place by the end of July and then adjusted that timing to the first day of school. There is no firm time table now. According to sources, Lightfoot is considering two outside finalists for the permanent position.

While the top post garners the most interest, the bench right below that carries out essential work in the district is thin and must be replenished by the next CEO. Not surprisingly, many people on Jackson’s team left after her announcement. Of 23 chief level positions in Chicago Public Schools, nine are filled with an interim staffer, are vacant or are about to be vacant.

Among them: the heads of operations, talent development, communications, college and career success and information technology. These include positions that decide which schools get renovated or get more social workers and nurses, recommend whether charter schools should be opened, renewed or closed and are responsible for getting laptops into schools and into the hands of students.

Will students show up?

Everyone hopes so, and efforts are underway to draw students back to class who struggled during remote learning. But CPS in June identified more than 100,000 students at risk of not showing up this fall.

This summer, Michael Deuser, one of the high-ranking officials who announced his departure, outlined one of the biggest challenges faced by the district: getting students to return to class and get back into the swing of school. Some of these students are at risk of dropping out or never making up what they may have missed during remote learning.

Average daily attendance at CPS high schools with almost all low-income students dropped by 20%, a WBEZ analysis of attendance data through the end of the third quarter showed. The school district has yet to release attendance data for the whole school year.

Meanwhile, the number of students receiving Ds and Fs increased dramatically at those same schools. Deuser, the head of college and career success, told board members this spring that the school district considers more than 18,000 students highly disengaged based on grades, attendance and other indicators. Another 85,000 are considered somewhat disengaged.

Deuser said the schools were directed to spend the summer making calls and knocking on doors to try to coax these students back.

“We want to give ourselves the best possible chance and be able to say that we’ve done all that we can to try to connect with every single student that’s out there,” Deuser said.

In addition, school district enrollment has been on the decline for about 15 years. Then, amid the pandemic, it plummeted. In just one year, about 15,000 fewer students were attending, a drop of 4%.

Some of the decline is among the youngest students, whose parents perhaps decided that they would keep their children in day care for another year instead of dealing with remote learning. The number of students in preschool went from 17,492 in the 2020 school year to just 11,494 in 2021. Kindergarten enrollment also dropped by 3,000 students.

The school district did an advertising blitz this past spring to try to draw these families back. But that effort might be derailed by the parents’ fears about the delta variant of COVID-19 as young children are not yet eligible to be vaccinated.

First day of school attendance numbers as well as annual attendance numbers, which are counted on the 20th day of school, will be indicators of whether the advertising blitz and the summer re-engagement efforts were successful.

Did students fall behind and, if so, how will they catch up?

Among educators, there’s a raging debate about whether pandemic learning loss or “unfinished learning” is a legitimate phenomenon. But Chicago Public Schools thinks it’s real and the school district is telling schools to help students recover by teaching them at their grade level rather than by trying to remediate.

Some teachers are dismissive of the idea of learning loss, saying their students learned invaluable lessons during this crisis, such as how to deal with uncertainty. They also say students always come into class at varying levels of ability and that they know how to deal with this and make sure all students move forward.

But the interim CEO Torres has said he thinks students lost a lot during the pandemic academically, as well as from a social emotional perspective. There is also evidence nationally from other states and researchers showing that students are behind in reading and math, with students and low-income students falling the furthest behind. It is one of the reasons Torres is insisting that school be in session five days a week with all students attending.

CPS did not administer standardized tests last year but, the number of students receiving Ds and Fs in math and reading increased last year, especially in the middle school and high school grades.

School district officials say research shows that the best way to catch students up is to accelerate learning, not to remediate. They say this acceleration — taking students who are behind and teaching them at their grade level — will be supported by 850 tutors that will strategically be placed in schools.

Officials also say they think the school district will be in good shape because it has rolled out new curricula for every grade and every subject. CPS spent $135 million developing the Skyline curriculum over the past several years, which it says will give teachers a bank of high-quality material from which to pull lessons.

However, teachers aren’t required to use the new curriculum and so its impact is likely to be uneven.

Parents and the public will also have to wait to see if the pandemic had a devastating impact on learning and whether students are recovering. The school district this year is dropping the standardized test it had been giving students for years. Officials say teachers can use tests associated with the new curriculum to assess whether students are learning and to adjust their curricula.

The state will test students in the spring so the big picture verdict on learning loss and recovery won’t be clear until next summer.

Sarah Karp covers education for WBEZ. Follow her on Twitter @WBEZeducation and @sskedreporter.