In theory, computer systems (not just automated systems) could be developed, which are able to take into account every failure or mistake to have ever happened in the history of transportation, and to evaluate all the probabilities of success and failure for every possible action and outcome.
In theory. In practice, we're still a ways off from doing that, although systems like IBM's Jeopardy contestant are headed in that direction.
But more to the point, when it turns out that there are still accidents, that are now "blamed" on the computer systems, will the developers now be blamed? And will we then want to automate the software developers? And when those systems are blamed, do we then develop automated systems to for developing automated systems?
The fact is that in the future, there will be systems which are more capable of evaluating all the risks and outcomes from all the possible actions, faster and more effectively than the human mind.
The question then will be, would you rather trust a piece of equipment or a human being who actually comprehends the concept of failure due to mistakes?