macos Sequoia causing problems with messages on mac

@hitbatsman A couple things for you that might help:

1. On the encrypt.me site, it says they just issued an update that has an option under the advanced settings to exclude Messages from the VPN. Not ideal, as you point out, but it may give you some relief until a better solution is available. I should note PIA has a similar feature, and it did not work for me. Your mileage may vary.
2. If you can export your config to WireGuard, then you can use the WireGuard app from the App Store (free) with your VPN config, and Messages will work again.

The trick is that if you use Apple's system VPN interface, so that you see the interface under the VPN section of the Network settings in System Settings.app, then it works. There seems to be a bug in Sequoia preventing VPN apps from working properly unless they go through the macOS VPN service like the WireGuard app does.

Again, both options are temporary workarounds. The WireGuard app has no kill switch and is pretty bare bones. The real fix is either going to be Apple rolling back whatever limits they placed on external VPNs, or every single VPN app vendor on the planet changing their design to use the macOS VPN service.

I'm an ExpressVPN user (and a very happy one at that). I turned off the kill switch as someone mentioned, and that worked for a time but not always. I continue to have to turn off the VPN to get the messages to go through.

The other thing I noticed, any anyone else?, sending messages, especially SMS Text to Android phones, is S L O W. Before the OS update it was lickety split.

Apple really needs to fix this at the OS level and regain the trust of their users. It has been sad to see Apple slip to far into the same issues that plaque so many other tech companies and platforms.

Don't reinstall your OS for this.

As a former employee... that's a cop-out on the part of the Novice Tech on the phone. During the entire 11 years I worked there, I never sent a customer to do that because it's a waste of time and a way to get you off the phone. DO NOT reinstall... (unless you want to) it won't make a difference. If you upgrade any OS to the first version of the release (ie. 15.0) ... you are taking a risk of it being buggy.

Also, NEVER Install a beta unless you are a developer... it connects you to APPLE Dev servers 24/7 to immediately report problems. It drains your battery being connected and it slows the system down. Don't use beta unless you are a Developer... don't let the nerdy kid down the block convince you that "Nah, it's ok... you get the new features before everyone else..." There is way more to it than features and you will hate the beta experience unless you are a developer. When it comes to releases, 15.0 is the final version released to the public. 15.0.1 means they had some immediate issues they had to immediately resolve. 15.1 usually takes a month or so and covers annoying bugs and new features that they didn't finish in time. You should always wait for the 15.1 version if you don't want to see bugs. (This is the same concept for Mac, iOS, iPadOS, everything in the world OS. lol

Clearly, this iMessage thing is a bug... so just hang tight and don't worry. When you call tech support on a new release version... you're wasting your time. Because often, even we don't know what the bugs are unless we are senior and we go through the process to look it up. Which can be a pill sometimes.

They will fix it cause Apple is good like that... just be patient and let them figure it out. You don't have to report every little thing cause as bad as this might sound; Apple Care won't know unless they kick it up to a Senior Advisor who knows how to research cases and that could extend your call to several hours because they will need to pull all your logs and diagnostics. (Which could help, but remember you're not the only Apple user out there; they can get the info from 10000000s of other people.

TankvilleFarmer wrote:

I haven’t had any issues with using the security measures of my choice together with Apple’s Messages until Sequoia but whatever helps you sleep at night..

I will repeat what I posted, which you apparently didn’t read:

When you install VPN it configures itself to the specific hardware, OS version and network that the device uses. If any of those change it can break the VPN. So any time you change any of these you may need to delete the VPN app and profile, restart your device then add them back (if you still want to use VPN) so it can configure itself to the new environment.

Express VPN apparently has a solution to this problem. I received the following message this morning but haven't had a chance to try it yet. It seems to involve downloading a new version of Express VPN. If anyone has a chance to try it before I do, would be interested in hearing about the results.

Stan, Oct 15, 2024, 2:16 PM GMT+8:

Hello,

Thank you so much for your prompt reply.

I am pleased to let you know that the issue with the iMessage feature on Mac OS 15 is now fixed.

To make sure that the iMessage feature will work, please follow the steps below:

• Make sure the Network lock is turned on
• Check the Allow Apple Services to bypass the VPN so iMessage and other apps work better
• Connect to the VPN
• Quit and Relaunch iMessage

Thank you for your patience. Please do not hesitate to contact back for any concerns - we'd be happy to help.

Regards,

Stan

ExpressVPN Support

Yes, as this thread is saying, VPNs do cause trouble, which wasn't the case the last 10 years, but it started with Mac OS 15.0.1

MartinJMannion wrote: Nothing happening on it with VPN on or off.

How about with VPN profile(s) completely removed?

With PIA, I have added the split tunneling entry pictured below in the PIA settings and that seems to work, for the most part, with my VPN turned on.

This should now be fixed as of MacOS 15.1. I also use Mullvad, but I believe other VPNs were having similar issues, as well.

I can confirm with PIA that I can send messages with the kill switch off. I am not getting notifications from the device, and I have to sync manually. But it definitely points to a problem with macOS routing Messages traffic differently. My guess is all apps will have to change the VPN implementation on macOS to use the builtin VPN service (the ones you see under Network Settings). Unless the VPN has an entry there, a lot of things seem to break.

@Cthulhu

Thanks for the tip! They pointed me to this walkthrough on their site. Basically sets up using your Torguard VPN natively through macOS (meaning you don't need the torguard app at all).

After doing that, Messages has been working as expected for me.

Here's how ExpressVPN works for me, sort of. I'm using, I believe, their latest: Version 11.59.0 (83862). The first Message I send can't be with ExpressVPN on. But once one goes through, then I can have it turned on for the rest of the day. To me that seems totally anomalous and I have no explanation why it might work. And what's weird too if that if, on my iPhone, there are messages sent last night while my Mac was off, they don't come through, until perhaps later when, I suspect, someone texts me a message. I'm not using iMessages on iCloud, that could be why. This whole thing is a ridiculous mess. I get, and appreciate, privacy and safety safeguards, but to take away useful functionality without justification, is just another tech bro hustle hubris mess. I do hope that the VPNs can pressure Apple to fix this in an update, yesterday even.

Cthulhu wrote:

That's not really accurate. The VPN app is independent from the configuration. Apps like PIA, WireGuard, and even Apple's settings allow VPN configuration changes without reboots. The issue we're all having is not solved by reboots or re-configurations. And I agree with others that Apple's security improvements have not caused me any harm until Sequoia. Actually, up until Sequoia I've had amazingly good experiences with updates considering the magnitude of changes from Apple.

That is all very well, but for at least the past 5 years when Mac OS or iOS are undated VPN frequently breaks networking. And the solution when it does is to delete the VPN app, test, then reinstall VPN. I’ve been responding to this after many updates. When you delete a profile on iOS it restarts on its own, without user intervention.

It may be more common with Sequoia, because the latest update merges most of Mac OS and iOS into a common build.

Hi,

As several users have already mentioned here, I'm also facing the issue with iMessage and SMS after updating to macOS 15 Sequoia. When connected to OpenVPN, I can't send or receive iMessages/SMS. Everything works fine when I'm disconnected from the VPN or using another VPN like ProtonVPN.

I've tried various configurations in OpenVPN (IPv6, DNS, TCP/UDP protocols, security levels), but nothing seems to fix the issue. It seems this problem is related to a change in macOS 15, as indicated by multiple users across different VPNs.

I'm adding my experience here to highlight the widespread nature of this issue, and I hope Apple can officially recognize this bug and provide a fix in a future update.

Thanks for your feedback, and let's hope for a quick solution!

The issue is not fixed in 15.0.1, at least in my experience. There no 15.1 yet. I use ExpressVPN. Here's how I have found it to semi-work: ExpressVPN is a startup item for me so I'm ready to go. To use Messages: 1. I turn OFF ExpressVPN. 2. Open Messages. 3. Send a message, ideally to another iMessage recipient but I don't really know if it makes any difference. 4. Once that message has been Delivered, turn on ExpressVPN again. Then Messages work as normal the rest of the day until I shut down my Macbook again.

For reference, I'm using ExpressVPN Version 11.61.0 (86322). A screenshot of my settings is attached. I found no difference whether the Allow Apple Services… selection is made or not.

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