What to do when kids bypass Securly on their school Chromebooks (and why they do it)
It was second period, and I was walking around the room while students worked on a research project. Most screens showed either a Google Doc or a tab from the library database. Then I noticed Maya’s screen change as I got closer—a flash of a blue and purple page, gone by the time I reached her desk. The Chromebook was warm, and she closed the lid a little too quickly.
I didn’t say anything then. Later that afternoon, I got an email from Securly: flagged activity, possible bypass attempt. It listed the time and the site she had tried to reach. It wasn’t a gaming site or a social media app. It was a YouTube video about the Revolutionary War.
This is the thing about school-issued Chromebooks: the filter works until a student decides it doesn’t. And at some point, most students who use these devices decide that. They find a proxy, a VPN, or a cached version of a blocked page. They share tricks in group chats. They do it less because they’re trying to hide something and more because it feels like a puzzle.
When I first saw that Securly alert, my instinct was to treat it as a discipline issue. She had broken a clear rule. The technology team had made the rule, and my job was to enforce it. But when I actually talked to Maya after class, she didn’t look guilty. She looked annoyed.
“Everything I needed was blocked,” she said. “The video our teacher linked was blocked, and the website we were supposed to use wouldn’t open on my Chromebook. It worked on my phone.”
I looked at her for a second. “Did you try asking for help?”
She shrugged. “What were you going to do?”
She had a point.
That conversation changed how I think about bypassing. Yes, rules matter, and schools filter websites for a real reason—to keep kids away from content they shouldn’t see and to keep them on task. But when a student bypasses the filter, it’s rarely because they want to watch something dangerous. It’s because they hit a wall and found a door. And once a kid finds a door, they’re not thinking about the safety system it’s designed to be. They’re thinking, I need this video, this game, this answer.
For parents, this can feel confusing. Your child comes home with a Chromebook, and you assume it’s locked down, monitored, and safe. Then one night you notice them typing a string of letters into a search bar that doesn’t look like Google. Or you get an email from the school about a blocked attempt. You might panic. But it helps to slow down and ask what your child was actually trying to do.
I’ve started handling Securly alerts differently. Instead of calling a student out publicly or sending a stern email home, I take them aside and ask one question: “What were you looking for?”
The answer is usually boring. A music video. A sports game. A movie they didn’t get to finish. Once in a while, it’s something school-related but blocked by an overzealous filter. Rarely is it something truly inappropriate.
From there, the conversation gets practical. If the student needed a site that was blocked, I work with them to request access or find an alternative. If they were just bored, we talk about what to do instead. But I’ve learned not to frame it as “you got caught.” I frame it as “when you hit a wall, here’s what you can do.”
That doesn’t mean pretending the filter shouldn’t exist. It’s a tool, not a scarecrow. But kids need to understand the why behind it. If all they know is that a website is blocked, they assume it’s arbitrary. They’ll try to get around it for the same reason they’ll climb a fence just to see what’s on the other side.
For parents at home, the things that actually help are pretty simple. Keep the Chromebook in a common area. Not because your kid is going to watch something terrible, but because it makes the device feel like a shared tool instead of a private portal. Ask them about the filter. Let them complain about it. Kids need to vent about how annoying it is that Roblox is blocked or that YouTube is restricted. If they can say it out loud, it stops being a secret puzzle to solve.
And tell them the truth: the filter isn’t there to punish them. It’s there because schools are responsible for what happens on those devices. When a kid bypasses the filter, they might think they’re proving they’re clever. But what they’re actually doing is turning a monitored space into an unmonitored one. And that’s a bigger deal than they realize—not because they’re “in trouble,” but because the protection exists whether they think they need it or not.
I’ve also started thinking about why kids care so much about getting past the filter. It has a lot to do with control. School asks students to follow rules all day. They don’t get to pick their classes, their teachers, or most of their schedule. The Chromebook filter is one more thing they didn’t choose. Breaking it is one of the only ways they can feel like they have a say.
That doesn’t excuse it. But it explains it.
One afternoon, Maya came back to me and said she needed a website for her history project, and the filter was blocking it. She didn’t try to work around it. She just told me. I checked the URL, sent a request to the tech department, and it was unblocked by the next morning. She said, “That worked?”
I nodded. “It’s faster than a VPN.”
She laughed. “But less fun.”
The bypass attempts will keep happening. There will always be another proxy site, another trick shared between friends. I don’t think we’ll ever stop every workaround. But the moments that matter are the ones when a kid doesn’t try to find one—when they just ask. It’s not a solved problem, and maybe it never will be. All we can do is keep the conversation open when that happens. That’s usually enough.
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