ESUHSD officials say housing costs, inflation, and job loss are just some of the factors contributing to the dramatic increase in San Jose.
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Blasa Ozuna is the district parent and community-involved specialist at ESUHSD.
"Nine hundred is the number today - the number tomorrow will be different. We are qualifying almost 100 new students every single month. We ended last year with a little over 1,200 students district-wide and we anticipate this year we'll be way beyond that number," Ozuna said.
The East Side Union High School District oversees 19 campuses with more than 21,000 students.
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School officials say inadequate housing looks different for each student - some are with their families staying at motels or shelters, or some are unaccompanied couch surfing.
"We've educated our staff on what to listen for - a student may not come up and say I'm homeless, but they may say 'Oh I've been sleeping on my friend's couch for the last week' or 'I don't have a ride to school, you know my dad just lost his job,"' Ozuna said.
In the past three years, the district has created a 'district parent and community involved specialist' role at each campus.
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For Day of Giving on Tuesday, the district and the East Side Education Foundation are launching a fundraiser.
It's to supplement the district's McKinney-Vento Program, a federal program created to protect and support enrollment and education of homeless students.
The district says 900 homeless students qualify for the program and they're trying to identify more.
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Maryam Adalat is the director of student services for ESUHSD.
"It's a sensitive situation while we don't want to be intrusive and ask all those questions, we're trying to find a way to be able to capture the information in a more gentle and respective way," Adalat said.
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In years past, school district officials say they've raised around $30,000 in order to provide $100 gift cards per student.
This year, they'll need to raise $90,000 in order to do the same.
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"We give our students a gift card as part of our holiday drive and they are often telling me - 'oh I'm going to give this to my mom for groceries' or 'I'm going to buy presents for my younger siblings' or 'I'm going to get my dad some socks' - you know we give them a bag of warm items and they're immediately thinking of their family members," Ozuna said.
To donate to the district, visit the East Side Education Foundation website here.
"We're shut down for two weeks over the break and we all think of rest and being with our family and enjoying that our students are wondering where they're going to have breakfast and lunch," Ozuna said.