An infrastructure “insurance” mechanism enables a Web site to fail over to a content delivery network (CDN) upon a given occurrence at the site. Upon such occurrence, at least some portion of the site's content is served preferentially from the CDN so that end users that desire the content can still get it, even if the content is not then available from the origin site. In operation, content requests are serviced from the site in the usual manner, e.g., by resolving DNS queries to the site's IP address, until detection of the given occurrence. Thereafter, DNS queries are managed by a CDN dynamic DNS-based request routing mechanism so that such queries are resolved to optimal CDN edge servers. After the event that caused the occurrence has passed, control of the site's DNS may be returned from the CDN back to the origin server's DNS mechanism.