There has been some good observations of failures to help customers affected by Iceland's volcano eruption. David Weinberger's blog has a typical posting http://www.hyperorg.com/blogger/2010/04/18/volcano-1-internet-0-01/. I think the roots to this problem are that money and effort is being spent on
1. style over substance, and
2. individual-casting over broad-casting.
The style over substance argument is very easy to see. Every travel website that I have used obscures the process's workflow (and the broader information architecture) with abusive Web 2.0 techniques. Most of these techniques require an inordinate number of communications between the browser and the server. The upshot is that under moderate load the website fails to respond with predictable timing. Without this predictability customers are greatly frustrated and this leads them to use a telephone where they can at least know what their predicted wait time is!
The casting issue is more difficult to see. There are more casting groups then just "me" and "everyone else". Depending on your service, customers can be group into multiple and overlaps groups. For example, specific airport groups, country groups, traveling with children groups, etc. Each of these groups have common and unique information and advice needs in times of emergency (and times of calm!). The general public group is, generally, the most useless group unless there is system-wide failure. Without addressing the needs of affinity groups you are not truly servicing the needs of your customers.
The upshot is, let's spend less money and effort on individual-casting with technical acrobatics and instead balance the money and effort on addressing the needs of individual and groups with predictability.
This posting was inspired by Mark Bernstein's posting http://www.markbernstein.org/Apr10/InternetFailure.html