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If the game prompts you on whether you want your runner to try and take an extra base, what it's really asking you is if you want to override the better judgment of your base coach. By design, the runner is usually going to get thrown out if you take that option, even if the ball is "very deep" and the fielder has a "poor" arm. If the runner is likely to make it safely to the next base, he attempts it without prompting you about it. The prompt is to cover extreme situations--once in a while you might want to send the runner even if you know he's going to get thrown out 80% of the time.
The one exception to this, for whatever reason, is sac flies: if the ball is reasonably deep and the runner isn't an ice wagon, he'll make it home safely more often than not.
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