Comment by jen729w

1 year ago

Vendors who block iCloud Relay are the worst. I'm sure they don't even know they're doing it. But some significant percentage of Apple users -- and you'd have to think it's only gonna grow -- comes from those IP address ranges.

Bad business, guys. You gotta find another way. Blocking IP addresses is o-ver.

> Bad business, guys. You gotta find another way. Blocking IP addresses is o-ver.

no, it's still the front line. And likely always will be. It's the only client identifier bots can't lie about. (or nearly the only)

At $OLDJOB, ASN reputation was the single best predictor of traffic hostility. We were usually smart enough to know which we can, or can't block outright. But it's an insane take to say network based blocking is over... especially on a thread about some vendor blocking benign users because of the user-agent.

  • I don't use iCloud Relay but it seems Apple's ASN would be 'reputable'.

    • Pretty sure the box with the "shield" icon on it, the ASN the web site would see, is, not coincidentally, CloudFlare?

      https://support.apple.com/en-us/102602

      "As mentioned above, Cloudflare functions as a second relay in the iCloud Private Relay system. We’re well suited to the task — Cloudflare operates one of the largest, fastest networks in the world. Our infrastructure makes sure traffic reaches every network in the world quickly and reliably, no matter where in the world a user is connecting from."

      https://blog.cloudflare.com/icloud-private-relay/

    • Only because without consumers using their IPs, they're a well established company with predictable uses. Once people use it for everything, then the reputation will drop.

  • Blocking based on ASN has never and should never be the frontline. It's the illusion of increased security with little actual impact. The bad guys are everywhere and if blocking an ASN has an improvement on your actual breaches then your security is total crap and always will be until you start doing the right things.

This would be weird, esp. given that Cloudflare is one of the vendors who act as exit nodes for iCloud Relay.

  • I believe your parent comment means when the target website blocks, not Cloudflare.

    YouTube is a perfect example. Using iCloud Private Relay can now frequently label you as a bot, which stops you from watching videos until you login.

    • Happened to me.

      Interestingly enough I checked on another non-Private Relay device (it worked), disabled Private Relay, refreshed the page, which still blocked me, and it resulted in the ban instantly extending to my other non-Private Relay devices.

      I presume some fingerprinting/evercookie was in place which led to a flagging/ban extension to my home IP.

  • I don't think that's weird. That's what I would want from an honest vendor who is involved in both services - block anonymization/obfuscation users if I'm paying you to block them. Apple/Cloudflare don't sell/support iCloud Relay as a service that is guaranteed to get you treated nicely by the parties on the other end, so they're not being deceptive with that part either.

    What I'd worry about is Cloudflare using their knowledge of their VPN clients to allow services behind their attack protection to treat those clients better, because maybe they're leaking client info to the protected services.

    Not that I think Cloudflare/Apple/etc. are supremely noble/honest/moral, or that it's good that semi-anonymous connections are treated so badly by default; this juxtaposition just doesn't seem like a problem to me.

    EDIT: OK, I back off of this position somewhat. Apple's marketing of iCloud Relay might allow users to believe it's more prestigious and reputable than a VPN/Tor. They do have fine print explaining that you might be treated badly by the remote services, but it's, you know, fine print, and Apple knows that they have a reputation for class and legitimacy.

    • > Apple/Cloudflare don't sell/support iCloud Relay as a service that is guaranteed to get you treated nicely by the parties on the other end, so they're not being deceptive with that part either.

      They really do, actually. The fine print on their page only states:

      iCloud Private Relay is not available in all countries or regions. Without access to your IP address, some websites may require extra steps to sign in or access content.

      And they have documentation linked on that same page for website owners: https://developer.apple.com/icloud/prepare-your-network-for-... which even goes a step further and encourages website operators to use Privacy Pass to allow iCloud Private Relay users skip CAPTCHA challenges.

      And really, this checks out, because iCloud Private Relay has a unique combination of circumstances compared to other commercial VPN users and Tor because:

      * It isn't explicitly designed as a bypass tool of any form like commercial VPN's, your options for IP location are "same general location" or "same country and time zone" - content providers have no reason to block it for allowing out of region access

      * Private relay is backed by iCloud authentication of both the device and the user, you can be beyond reasonably sure that traffic coming from an iCloud Private Relay endpoint is a paying iCloud+ user, browsing with safari, using their iPhone/iPad/Mac.

      * It is backed by one of the most recognizable brands in the world, with a user base who is more likely to send you nasty messages for blocking this service.

      On particular note of the last one, there's no "exception list" or anything available for end-users in Safari to bypass Private Relay for specific sites. My work one day decided to add the entire "Anonymizers" category to the blocklist in Okta, and I was suddenly unable to access any work applications on my iPhone which is enrolled in our enterprise MDM solution because I have Private Relay enabled. Enough people complained that the change was rolled back the same day it was implemented, because the solution was "turn it off" and that was unacceptable to many of our users.

I’ve noticed wifi at coffee shops, etc have started blocking it too.

I need to disable it for one of my internal networks (because I have DNS overrides that go to 192.168.0.x), or I’d wish they’d just make it mandatory for iPhones and put and end to such shenanigans.

Apple could make it a bit more configurable for power users, and then flip the “always on” nuclear option switch.

Either that, or they could add a “workaround oppressive regimes” toggle that’d probably be disabled in China, but hey, I’m in the US, so whatever.

Edit: I also agree that blocking / geolocating IP addresses is a big anti-pattern these days. Many ISPs use CGNAT. For instance, all starlink traffic from the south half of the west coast appears to come from LA.

As a result, some apps have started hell-banning my phone every time I drive to work because they see me teleport hundreds of miles in 10 minutes every morning. (And both of my two IPs probably have 100’s of concurrent users at any given time. I’m sure some of them are doing something naughty).

Wait, this comment made me aware of the existence of iCloud Relay. Apple built their own Tor only for Apple users? Why would they do that? Why not use Tor???

  • You can use iCloud Relay without even noticing that you are using it, this is not true with Tor as you'll spend most of your time waiting for reconnecting circuits.

    • That doesn't line up with my experience at all.

      You will still notice when some sites completely block you, of course.

Well its primarily because the security vendors for say WAFs and other tools list these IPs in the "Anonymizers" or "VPN" category and most typically these are blocked as seldom do you see legitimate traffic originating to your store front or accounts pages from these. Another vendor we use lists these under "hacking tools" So your option as a security professional is to express to your risk management team we allow "hacking tools" or lose iCloud Relay customers. Which way do you think they steer? In alternative cases a site may use a vendor for their cart/checkout page and don't even have control over these blocks as they are also blocking "hacking tools" or "anonymizers" from hitting their checkout pages.

  • > So your option as a security professional is to express to your risk management team we allow "hacking tools" or lose iCloud Relay customers

    a professional would explain how the vendor is being lazy and making a mistake there because they don't understand your business.

    depending on the flavor of security professional (hacker) they might also subtly suggest that this vendor is dumb and should be embarrassed they've made this mistake, thus creating the implication that if you still want to block these users you would also have to be an idiot

    under so circumstance is what I ever allow anyone to get the mistaken impression that some vendor understands my job better than I do. As a "security professional" it's literally your job to identify hostile traffic, better than a vendor could.

  • Oh I think we all know that the Endgame is only allowing the approved webbrowser from the approved hardware. And getting on those lists will be made very expensive indeed...

  • Wait till you see how M365 does management around iCloud relay makes it real fun troubleshooting suspicious login parameters...