I believe the interesting issue here is not whether Mr. Winter was violating the terms of the agreement - but the manner in which violations are handled, and the absence of a meaningful "feedback loop" where users of the system could be warned and have the opportunity to modify their behavior to follow the rules.

I assume the underlying cause for this is that the AdWords program is as automated and algorithmic as possible. The less Google has to pay for human beings for time and effort to administer it, the better it works. The very nature of AdWords and why it has been such a successful product depends on the scaling properties of algorithms and server farms.

The old-fashioned traditional world based on human beings making decisions has a lot of give and take to it, with humans negotiating with each other about exactly what the rules mean and how to apply them. We are moving to a world where automated systems are responsible for monitoring and enforcing rules, and that involves a lot of tradeoffs. I understand the benefits to be gained - but its hard for fallible human beings to understand and follow complex rulesets enforced by merciless machines.