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I would like to add an OpenVPN service (for personal use) to a machine I already have an obfuscated Tor bridge running on (for shared use). I would like the option to access this VPN through obfsproxy, while still allowing for Tor to have its own managed obfsproxy (both running obfs3).

Is this a problem? Do I simply fire up a new, non-managed obfsproxy instance for the VPN?

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As long as each obfsproxy instance binds a unique port, you can have as many of them as you have the resources to run.

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