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@ -372,7 +372,7 @@ class Connection(ConnectionBase):
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# wait for a password prompt.
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state = states.index('awaiting_prompt')
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display.debug('Initial state: %s: %s' % (states[state], self._play_context.prompt))
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elif self._play_context.become and self._play_context.success_key:
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elif self._play_context.become and self._play_context.success_key and not self._connected:
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# We're requesting escalation without a password, so we have to
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# detect success/failure before sending any initial data.
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state = states.index('awaiting_escalation')
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