MacOS Sequoia blocking VPN, won't allow use of Messages and iCloud

On a MacMini M1, MacOS 15.


I've been using ExpressVPN for years for my work, recently I discovered I can't use iCloud while using VPN. I could work around it by simply using it on my phone, but it wasn't optimal. I also can't airdrop while using VPN.


Now in this latest update, the MacOS is actively blocking my messages while using VPN which is a big problem now as my clients communicate through that.


I can't whitelist anything through ExpressVPN and I don't see what I can do in MacOS since I can't do anything to adjust this. It went from working to not working after the update.


Anyone else having this issue? I'd love a work around as right now, it's not at all ideal with the new OS. Most of the features that I looked forward to aren't even available in Europe which makes no sense. I somewhat understand the AI issue, but the screen sharing with your iPhone isn't available? Why? If I can screen share with my local machines why not the iphone? Something doesn't sit right with me in these latest updates.


Any help would be appreciated. Thank you in advance


PS. How can I downgrade if I have to?

Mac mini, macOS 15.0

Posted on Sep 17, 2024 8:31 AM

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Question marked as Top-ranking reply

Posted on Oct 27, 2024 11:36 AM

I worked with Express VPN support and was able to get things to work.


TLDR:

  • Download the latest Mac client from Express VPN (they've made an update - more on this below)
  • Completely uninstall Express VPN - I used AppCleaner to remove left over files
  • Uninstall the left over IKEv2 Network configuration
  • Reboot
  • Install newly downloaded version of Express VPN
  • Login and configure Express VPN but do not select the new "Allow Apple Services to bypass VPN checkbox" - more on this below.
  • Enjoy


Further history:

  • I was unable to get iCloud drive, notes, or messages to sync
  • The only workaround for me that worked was switching to IKEv2 (you have to turn off advanced protection to do that).
  • I reached out to support and had a long chat where we tested many things.
  • They have created a new version with a new checkbox to allow Apple Services to bypass VPN. See https://www.expressvpn.com/support/knowledge-hub/network-lock/#apple-services
  • For some reason Express VPN did not suggest the update. Maybe it is on a rolling canary and it would have in the next few weeks.
  • I installed the new version on top of the my existing version and tried enabling the new setting based on advice from support.
  • This messed my machine up further. iCloud stopped syncing even when quitting Express VPN. I tried multiple configuration permutations but could not sync.
  • I told support I was going to do a full uninstall and did the steps listed above. At that point it was working even without turning on the new "Allow Apple service to bypass VPN..." checkbox.
  • But I was curious and checked it and did more testing. It seems that did allow Messages to work. But iCloud drive and Notes would not sync. My suspicion is that in a rush to fix it they only tested Messages and somehow made things worse for the other Apple services.
  • I've gone back to using what is working for me which is the uninstall / reinstall of a the new version with the settings I normally used (auto protocol, Advanced Protection turned on, network lock and allow access to network devices. But I did no not have "Allow Apple Services...".
    • Note that this new setting like the Allow network devices setting is tied to network lock. If you do not have network lock enabled, it is irrelevant and apple services will work regardless of it being set.


All of this makes me wonder if the change Apple made is causing issues with pre-installed VPNs but somehow allows traffic for newly installed ones. It seems to either be that or some other change Express VPN made in the new release.


I hope this helps someone else.


95 replies

Sep 20, 2024 9:23 AM in response to Oberon-Station

I don't think you can get all that from macOS as easily as through Express VPN. You have to do a little more work to get similar functionality. macOS has the Private Relay (requires iCloud+) which can do much of what Express VPN can do to hide your IP address so websites can't detect it and hide the websites you are visiting from you internet provider (only in Safari, though). In Safari you can also prevent cross-site tracking through a setting in the Privacy section. I also have AdBlock Pro installed (the non paid version) to eliminate ads. All this is a bit piecemeal and doesn't offer the big switch that sits on the main pipe of your internet connectivity and thus works on everything on your computer like what Express VPN offers (unfortunately).



Sep 20, 2024 1:55 PM in response to ottmar288

ottmar288 wrote:

I don't think you can get all that from macOS as easily as through Express VPN.

Why do you believe you need to "get all that?"

Stop listening to the hype designed to sell those products. I would call them lies, but that are at the very least extreme hyperbole. There aren't hoards of baddies lurking on the internet trying to steal your personal information.

Effective defenses against malware and ot… - Apple Community


Sep 20, 2024 2:20 PM in response to Barney-15E

As an information security professional, your advice is irresponsible, and some items in the link are uninformed or out of date. Many of us require a VPN for work, many of us for travel, and others use them to greatly reduce the advertising traffic which, if you've ever used one, you'd know can be a transformative online experience.


Please everyone saying "just stop using the VPN" - stop giving us advice. If you have no helpful advice on the topic, please just stay silent.


So many of us are reeling from the loss of services after this update, and we're trying together to find a solution. The solution is not to stop using a VPN. Just move on, please.

Sep 20, 2024 5:10 PM in response to Cthulhu

Cthulhu wrote:

As an information security professional, your advice is irresponsible, and some items in the link are uninformed or out of date. Many of us require a VPN for work, many of us for travel, and others use them to greatly reduce the advertising traffic which, if you've ever used one, you'd know can be a transformative online experience.

Please everyone saying "just stop using the VPN" - stop giving us advice. If you have no helpful advice on the topic, please just stay silent.

So many of us are reeling from the loss of services after this update, and we're trying together to find a solution. The solution is not to stop using a VPN. Just move on, please.

We’re not talking about an actual VPN needed to access an internal network. Those are necessary, but don’t work for the same reasons.

The crap they promote to protect you from the hoards of baddies is all hyperbole designed to scare people into using absolute crap they don’t need.

The people using the crapware “VPN” software can get back to working by u installing the crapware they were fooled into installing.

Oct 1, 2024 3:44 PM in response to asdfdsfasdfasf

You should avoid making untrue inflammatory statements. There have been well-known and publicized (including by Proton) issues with leaks on iOS. The last substantive update to that is documented here - https://protonvpn.com/blog/apple-ios-vulnerability-disclosure/...which is specifically about DNS and pre-exisitng connections (and mitigated when Apple provided a kill-switch in their VPN framework).


Even so, connections or DNS requests leaking outside a VPN is very different from leaking to Apple's servers, which implies that the connections that ought be going through the VPN are instead going to Apple's infrastructure, rather than directly to the intended end-point outside the VPN tunnel.


It similarly implies that Apple may be logging and tracking those connections (as opposed to an ISP logging and tracking...).


Apple may very well have made changes to their Framework APIs that introduced a bug - but there is quite a difference between using Apple's APIs and using Apple's infrastructure.


On the other hand, perhaps I'm wrong and you have discovered that Apple is MITM-ing all VPNs in Sequoia...in which case you should publish your technical findings and become the darling of the ITSEC community for the next 15 mins (and you absolutely would be if that were the case).

Oct 1, 2024 5:47 PM in response to Cthulhu

The specific post I responded to says "I investigated how protonvpn works - it leaks everything to apple servers, does not send over VPN." (emphasis added).


Perhaps just sloppy language, but the way it is written does carry the implication that all traffic outside the VPN is going through Apple's infrastructure - the plain reading of "leaks everything to apple servers." That's quite different from Apple services going to Apple (which isn't a leak to Apple in any case because those services have to go to Apple, VPN or not).

Oct 1, 2024 5:55 PM in response to Cthulhu

Cthulhu wrote:

@g_wolfman I don't see anyone saying any of the things you posted.

There is a link to the original post being responded to in each reply. See here:


Unfortunately, the current version of the forum software has this funky default sort order by "rank" that can be very confusing. See:

I've changed mine to "Newest" in my preferences.


It's a real problem on some of these new Sequoia threads. People keep replying with the same problem, apparently not seeing the fix. At least I would expect to see the typical freak out about not running the firewall. Perhaps they just don't bother searching, but I think the sort order does contribute.


Can you elaborate what inflammatory statement you refer to and what untrue statement you are referencing? I must have missed where anyone even implied Apple is MITM'ing VPNs.

It's just typical internet misinformation. People often think that Apple is just a typical flaky tech company and all those social media influencers are trying to protect us from Apple's poor security. But if Apple really had such poor security, why would its biggest competitor set up an entire division just to hack Apple devices? Denigrating Apple has always been a popular pastime in certain circles, but now it's a full-fledged industry. But it's all fake.

Oct 1, 2024 6:49 PM in response to etresoft

Well, admittedly my comment about MITM was a bit hyperbolic...


But the post I was replying to made a hyperbolic comment about everything leaking to Apple servers, and the post I replied to started with the words "I investigated". I don't think it's out of the realm of possibility for someone to read that and come to a worst case conclusion - a mistaken one of course - that all their data is going through Apple's servers. Which is the definition of MITM.


So to be clear, I didn't actually say the person I replied to implied Apple was MITM anything, but that their imprecise language and the claim that they investigated the issue, could lead others to that sort of conclusion

Oct 1, 2024 7:00 PM in response to Cthulhu

I agree with everything you just said - didn't see that level of precision in the post in question, though.


Although one point maybe worth noting - Apple is the OS developer, so the idea that "Apple" doesn't know your real IP even with the VPN working perfectly is a bit silly. macOS is almost certainly not sending that kind of telemetry to Apple, but that is because Apple is basically trustworthy - and it is a trust thing.

Oct 2, 2024 4:52 AM in response to g_wolfman

g_wolfman wrote:

Well, admittedly my comment about MITM was a bit hyperbolic...

Don't mind me. I was just pointing out a few "features" of the forum software that people might have missed, perhaps due to the grey-on-white text.


Alas, there's nothing that can be done about internet misinformation. Probably our last hope now is that AI chatbots will be able to inject some sanity and reason. It seems like those are the only thing people believe anymore.

Oct 4, 2024 10:57 AM in response to Oberon-Station

Same Problem here ( Germany ). VPN configuration blocks at least iMessage.

Update to 15.0.1. does not solve the issue. Downgrade is a **** of work. So I have to

select: No Facetime, no iMessage on my Mac or reduce security by switching VPN off.

The answer should be clear for all of us...

Apple did a very bad job here! This should be obvious and has absolutely to be tested before announcing a global update.

What a shame

Oct 7, 2024 2:58 PM in response to etresoft

etresoft wrote:
But that is a very important debugging step. If you turn the VPN off and that corrects the problem, then you know, with certainty, that the VPN is the problem.

Using the same logic: if you upgrade the OS and that breaks Messages and other apps while using a VPN, then you know, with certainty, that the OS is the problem?

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MacOS Sequoia blocking VPN, won't allow use of Messages and iCloud

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