Mathew Patterson from Campaign Monitor:
Being correct is important; the friendliest, most helpful response will still cause problems if it isn’t accurate. It just isn’t enough to churn out the correct answer.
Mathew’s experience is one I’ve run into as well. Sure, your app may not be able to technically do something exactly like I want, but there might be another way I haven’t thought of. Make sure to give your customers som alternatives to help them. As long as they get where they’re going, the route they take isn’t as important at the moment.