Earlier quoted context omitted.
> How would an attacker learn of the private key server? If they're using CloudFlare and they're a large financial institution we'll just assume they're using this new service. Now we just need to find the location of the keyserver. There's a variety of ways to locate a server when you don't know where it is. The default is to scan the target's network. To find the network you can look at the ARIN info for addresses…
This is CloudFlare's entire core business model . CloudFlare is just a reverse proxy+cache. The original web server is still run by whatever company is using their services. Fixed: "If they're using CloudFlare and they're a large [anything], we just need to find the location of the [origin webserver]." This hasn't been a problem for any of their customers that do this so far (hint: all of them), adding a keyserver is…
To give you an idea how this affects people in the real world, some websites will make thousands and even millions of dollars an hour in advertising revenue and paid services. They depend on CDNs to handle the traffic of that many users and make it seem like everything's moving smoothly even in the event of a temporary outage. If that site goes dark completely, they lose tons of revenue, and people get fired.
In another case, let's say a large financial institution, they might need to provide authoritative and highly sensitive information around the clock to organizations that basically control the flow of money around the world. Downtime isn't really an option. Without Keyless, this information stays up, cached. With Keyless, an outage can make this information disappear, with potentially far-reaching global financial repercussions.
To reiterate: if you don't use Keyless, your (HTTPS) static content stays up under an outage. If you do use Keyless, your (HTTPS) static content goes dark under an outage. (For https clients that don't have an existing valid session ticket on the CloudFlare server)
You can always use plain HTTP and avoid the outage, of course. But for large financial institutions that's probably not an option.
Also, please note that i'm really not trying to be inflammatory. I'm just pointing out that this is a new, additional point of failure and it can have real consequences for the content people provide over HTTPS.