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Is it illegal to bypass blocking in Iran? I know in some countries it's legal to bypass such blocks if you can, even if a government tries to block proxying as well.

In Russia there is no punishment for bypassing blocking. But if you publish information about bypassing or proxy server addresses, your site will be blocked too (but no punishment for you personally).

The same is generally true in Iran based on my experience.

It technically is, but such a huge number of people use vpns. I know 14 year old children who use commercial VPNs to watch YouTube.

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