Airvpn, then use their advanced config to create a 443 tcp tunnel out to a single server. Then use that server’s IP in your OpenVPN config file. Route all traffic including dns inside the tunnel.

Traffic will look like all other web traffic - encrypted on standard web ports. You won’t even need to do a DNS lookup to start with and airvpn uses generic rDNS so it’s not super easy to figure out from their perspective.

Typically, using your own VPN should suffice. Depending on your situation you can do other things as well. If you are unable to download these tools on the school network in question; do not attempt to do so again. Use a public or other network connection elsewhere to obtain the tools you need to bypass their crap.

For example, NextDNS could be helpful. By running their client app; ( https://github.com/nextdns/nextdns/wiki/Windows ) you can make sure all your DNS requests are encrypted. Similarly you could simply set up a local DNS server that you point Windows at which can redirect those requests over DNS-Over-(HTTPS or TLS) to a DNS provider of your choosing.

DNS over HTTPS is your best bet because they can’t Man In The Middle and replace it (DNS Poison) like good old DNS. They will still be able to see the IP addresses you are connecting to unless you proxy those connections. nativeproxy uses Chromium’s stack so it is much harder to detect. There are UI frontends for it if you prefer but I’ve never used them. ProtonVPN also has a stealth protocol that I’ve heard is good, though I don’t know too much about it.

Good on you for trying to get around it. That kind of curiosity is a great way to develop your lateral thinking skills. You didn’t ask for a lecture and people giving you one should go back to stack overflow comments. If you want to take the risks of it, that is up to you and you are likely to fuck up. That being said, you aren’t the only person likely go get in trouble if you fuck up and, unlike you, IT will depend on their job financially. If you do it well enough and make sure you don’t get caught by someone seeing your screen or blagging around the school that you did it, that won’t be an issue.

IT departments also read comments in threads like this to find the current trends of how students are trying to get around their web blockers so keep in mind that you will need to keep your skills up to date.

Seems like Tor snowflake is a proxy that makes your internet traffic appear as a video call. Its purpose is to circumvent censorship, but it may get around firewalls as well. I have no experience bypassing firewalls using snowflake, but it may be a viable option (someone correct me if I’m wrong) https://snowflake.torproject.org/

Don’t use the school’s wi-fi? I’m sure there are other options to you.

You’re going to get in trouble and it’s not worth it.

Don’t do personal stuff on their network. What are you even trying to look at via the school network?

If you’re concerned about privacy while doing school stuff, use another device, or maybe a VM. Do they provide computers for students?

You might get off with a warning because you’re young (I assume you’re like 16), but bypassing network security stuff as an adult at work will often get you fired.

Sounds like DNS blocking. Use DoH, won’t be as good as a VPN but it will stop the sniffing which allows them to block domains

If you try to browse to the tailscale website does it work?

If it does you could setup tailscale with an exit node at your house and tunnel your connection that way? Everything would then be coming from your home internet. I have had good success with tailscale being able to punch a hole through some pretty filtered firewalls.

Don’t use the WiFi if you don’t like the rules

Please read Charger8283’s reply. It’s the best one. You’re thinking small, how do I break out of their system, that will only land you in trouble. You should think big like how Charger8283 thought and break the system altogether.

If you first find vulnerabilities and report them to your school, later when you find another one you don’t tell them about it until they ask. Keep it a secret and use it for a while. Just pretend like you weren’t ready to tell them because you didn’t understand it yet.

Sometimes it pays off to play nice and stupid.

Here are some good rule of thumbs for work and schools:

• do not connect to their networks with your personal devices, ever.

• Only use work/ school devices on their own network.

• Do not do anything personal on those networks. only do work/school related tasks. This means don’t log into any non school/work accounts.

• If for some reason they don’t have a device for you but require you to use their network, then leave your personal devices at home claiming you don’t own one and make them accommodate you.

You cannot expect privacy in these situations, and by going to the extreme lengths to try to get it then you will ironically just paint a bigger target on your back if any network admin cares. In some cases this can cost you your job or get you in trouble with the school.

Use Tor with bridges, or orbot if you want to use apps.

I’m assuming you probably have a smartphone. In which case, I would just use your Wi-Fi hotspot instead.

At the risk of sounding contrarian/lame, you should probably not be doing any of this especially if you don’t own the hardware you’re using (as mentioned by another commenter).

You don’t specify if this is university or middle/high school, but either way you are not entitled to and should not expect any privacy on a network you don’t control. Even if you are able to set up a VPN to mask your internet activity, your school’s network administrators almost certainly can tell that you are using a VPN, which itself sounds like it would be a violation of your school’s network policy and will most likely land you in trouble. Indeed, your repeated attempts to access blocked sites have likely already raised some flags.

Even the workarounds that others here have mentioned (like routing VPN traffic over port 443) are inadequate for a network that is being actively monitored. Believe me, it is very easy to tell when someone is connecting to a VPN this way.

I would quit while you’re ahead until you can afford your own hardware/internet connection, and then maybe worry about any notion of privacy. Use your school’s internet for what it was intended.

If you don’t need a speed and full functionality of the Internet.
Try bridges for the Tor Browser.