iCloud Relay Uses "Bad" IP Addresses?

I have iCloud Relay turned on for my Macs. It has worked well with no problems. However, I also own a Windows Gaming Laptop (used only for MS Flight Simulator) and I try to keep up with Windows issues than might affect the laptop so I subscribe to the “Ask Woody” Windows support site. When I try to post to the Ask Woody forum from Safari on my MBP16 M3 system, it is blocked because Relay is using an IP address associated with Spam and other bad behavior - the IP was 104.28.85.95. (https://cleantalk.org/blacklists/104.28.85.95). Seems pretty odd that Apple would use a “bad” IP address. Has anyone run into this situation? I can turn off Relay or post from Chrome instead of Safari and it should work - but this is the only time I have seen this issue. (It happened twice with this website, so it isn’t a one-time problem.)

David

As with all things, you need to look a bit deeper.

This IP address isn’t owned by some spamming company. If you look down at the details of the listing you cited, that address is owned by CloudFlare - a major cloud hosting service provider.

It is likely that that address is dynamically assigned to all kinds of cloud services at various times, including Apple, it would seem, and almost certainly also including some spammers before they can be found and kicked off the service.

Also note the dates on the report. Spamming was discovered on May 4th, and the last activity was June 4th (two weeks ago). So it would appear that the problem user was already kicked off the service.

I suppose Apple could work around this by only using IP addresses that they own, but that would pretty much undermine the point of private relay, since everybody would know the message is being relayed through Apple servers.

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Thanks. That’s pretty much what I figured. Ask Woody isn’t going to change, though. I don’t really need to post - just saw something weird in Windows Task Manager (FS2020 was buried in the “Widgets” category - something new that they inflicted on everyone). I turned off Widgets and it is back to normal. MS hasn’t changed much with regard to Windows updates - it hasn’t improved, for sure.

David

I suppose you could use the Ask Woody web site to participate in the forums, if they’re blocking e-mail access.

And hopefully, the Cleantalk service will remove the blacklist entry soon, if CloudFlare has properly banned the offending account.

And, of course, iCloud Relay may also jump to a new IP address, which may or may not work better.

… Wait a minute. I may have misread your article. Are you saying that the forum is blocking WEB access requests from that IP address, even though the blacklist report is about e-mail spam? That sounds unnecessarily aggressive.

It did list one report of someone trying to brute-force an attack from that address, but that was two years ago - which should not be considered a red flag today.

Yep - they block posting from Safari. My email goes through. I really don’t care - their forums are pretty much a mess and hard to navigate (the complete opposite of the TidBits forum!). They publish a weekly newsletter that is sometimes helpful - I just ignore all the stories about Widows apps. I just follow their recommendations on whether or not I can apply the monthly Windows updates.

So many of their users also use Apple devices (iPhones, iPads, etc.) that they have recommendations for Apple updates too - and some commentary on the Apple universe, which can be interesting given where they are coming from.

David

You can turn off private relay for a particular tab. View menu, Reload and show IP address. You’ll get a system dialog telling you that the website will see your real address.

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This is a completely different approach to ‘solving’ the problem, but have you tried using Whisky to run MS Flight Simulator directly on your Mac? If it performs sufficiently well it could remove the whole headache of maintaining a Windows laptop.

I used Boot Camp on my iMac Pro (Intel) - no problems with performance, but lots of problems with maintenance of the Windows software. I have the MSI Laptop so I will keep it as long as performance is OK. MS FS2020 is being supplanted by FS2024 (or FS2025, I don’t know what they will call it) which is likely to require even more resources. I could also use X-Plane which runs on both MacOS and Windows but it doesn’t have the scenery of FS2020 - which I like. I think there is also a chance that MS will move off Intel in the future - but that is just a guess.

David

The advantage of Whisky is that there is no Windows software to maintain. It’s based on Wine which translates Windows APIs to Unix ones so you don’t need the Windows OS to run Windows software. The disadvantage can be compatibility, performance, etc. But if it works it is much simpler than a VM, Boot Camp, or separate PC. If the Windows laptop works for you I’m not trying to convince you off of it, just explaining the Whisky option in case it’s of use at some point.