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> What is the issue with this request?

I didn't realize this was an Apple thing, but that's fine. It changes the color of the horse and the name of the river, but the same road leads to the same destination.

1) There is a notion that Cloudflare is a content distribution network. The risk profile for a content distribution network is different from a VPN service. Now I know it's a VPN service (or is it?). Changes it from "seems weird and inappropriate" to "do I care about people relying on this? no, probably not". Cloudflare can't be arsed to provide reverse DNS for something which is clearly not part of their CDN, or is it?

1.5) Is it layer 2 or application? Cloudflare runs a CDN. Correct me if I'm wrong, but the CDN is a reverse proxy is it not? Is Cloudflare caching my website's content? Can they observe it? (It's surprisingly hard to find a solid explanation, but they talk about "proxies" and "decrypts the name of the website you requested" and none of that adds clarity, it makes it sound more like believe what we want you want to believe.)

2) I don't block incoming SYNs from Cloudflare (yet) the way I do with Amazon, and this traffic per se isn't going to trip any mitigations here. But not all of the traffic is as benign (and it's impressive that they're so technically savvy they don't need the CSS as noted elsewhere). Presumably those exit points are shared by multiple customers. Did I mention I block all incoming SYNs from Amazon?



> and it's impressive that they're so technically savvy they don't need the CSS as noted elsewhere

With the logs you provided, they appear to be coming from within iMessage.

So when someone posts a link in iMessage it will fetch the favicon(s) and the html in order to generate a “preview” of the page with the title of the page and use one of the favicons. It doesn’t need to fetch any css files to do this.

Not saying bad actors don’t fetch css either, but the lack of it being fetched doesn’t mean that it’s a bad actor.

As for why CF don’t reverse DNS their IPs stating it’s iCloud private relay, well CF are not Apples only 3rd party egress provider (Akamai are also one that springs to mind). So if the number of providers can change at any time, the best source of information about valid egress providers is from Apple themselves.

But Apple do also publish these changes to geo-location databases for you to query, for example: https://www.ip2location.com/demo/104.28.42.8 lists it as iCloud Private Relay.

As for “are CloudFlare caching my site when ran through private relay?”, not 100% sure, I’ll have to check my own logs and cba’ed right now, but I don’t think so (it’s been a while since I ran tests on it to see how it behaved to be 100% sure right this minute.

But I think it would be silly of them if they did as they may not be aware of the what to cache and for who. Let’s say they cached /profile without knowing what the server is using to determine who the logged in user is, they may false cache-hit and leak data from a previous request. When they act as your sites CDN you explicitly tell them what to cache on, but when acting as a relay (either for apple or their own warp product) for a site they are not a CDN for they are missing this info, sure they could guess, but why risk being wrong?)


Thanks for the explanation.




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