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Is it a good idea to establish bridges within repressive countries (China, Iran, etc.), or a bad idea?

On one hand, having the bridge within the country removes the "foreign" stigma from that IP address for purposes of filtering/censorship. On the other hand, does this mean that the bridge will then attempt to connect to a published relay IP address, making it obvious that it is an entry node?

Considering this topic in light of Belarus's recent ban on Tor.

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It depends on the country and how repressive it is. For certain countries, running bridges is considered a bad idea to the point where even if one is provided, BridgeDB will never distribute it to clients.

See ticket #12843 - " Bridgedb shouldn't handout bridges from .ir and .sy" for concrete examples of this including the rationale.