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The engine now opens the TCP connection to a CONNECT's server before it answers. When the server can't be reached, the CONNECT gets a 502 (or a 504 on a timeout) and the client reports its own connection error, rather than a 200 followed by a 502 inside the decrypted session or a silent hang-up in a tunnel. The failure is recorded as one error flow. The dialled connection is handed to the tunnel, or to the first upstream connection of a decrypted one, so nothing is dialled twice. Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>