macos Sequoia causing problems with messages on mac

NotSoTechnical wrote:

Yup, I run OpenVPN 24/7, and have been having problems sending messages since upgrading to Sequoia. Turning off my VPN allows the messages to go.

I rarely experience bugs with Apple software, but this one is a major foo bar! Let's see a fix, Apple!

And in your mind it’s impossible that it is a problem with OpenVPN? Really? Have you considered this:

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 iPhone, iPad or Mac then add them back (if you still want to use VPN) so it can configure itself to the new environment.

It is frustrating that no one from Apple has weighed in on this thread.

Some more information from my testing:

This issue seems to only affect standalone VPN clients from the VPN providers themselves. That means that if your VPN provider has Wireguard configuration files, you can download Wireguard from the Mac App Store and use those configuration files to connect to your VPN and still send and receive messages with your VPN active.

I haven't tried the OpenVPN client but presumably that would work too. However, since the OpenVPN client is not available in the Mac App Store it might also have issues. If anyone is willing and able to test that as a workaround please post in this thread and let us all know.

It sounds like some of the VPN providers have been able to update their client apps to work around this issue, which suggests that Apple may have made a network change to the OS that they don't consider a bug and have no intention of fixing. That may also mean that any changes the VPNs make to their respective client apps may break with future macOS updates. That is total speculation on my part, however.

Lawrence Finch wrote:

Macs Pain wrote:

I never thought the VPN could be the issue... Apple fix this ASAP, please.

There is nothing for Apple to fix. Regardless of what you thought, VPN can be the issue. Here’s the short answer:

When you install VPN it configures itself to the specific hardware, OS version and network that the phone 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.

Here’s the long answer→VPN: What you need to know - Apple Community

Yes, my boilerplate response, that I use several times a day, was written for an iPhone answer, but the same applies to any device, Mac, Windows, Linux, etc. But thanks for pointing that out; I’ve now fixed it in my Notes app.

Adding some more detail to this. I've tried two different VPNs, three different VPN protocols, and a variety of different settings but whenever a VPN is active, I cannot send or receive messages OR NOTIFICATIONS of any kind. As soon as I disconnect the VPN, messages are sent and notifications are received. This is an issue on my M1 Max 16" 2021 Macbook Pro and my daughter's 2023 M2 Macbook Air.

This worked for me:

1. I disconnected the VPN (Check Point to get to my office network)
2. (iMessage was still not working for me at this point)
3. In Messages I opened Settings
4. On iMesage tab I clicked Sync Now
5. (iMessage started to work)
6. I reconnected the VPN

Now I am sending and receiving iMessage and SMS on my Mac.

Following below is the message I received from Express VPN support today, suggesting the same "solution" we've all been talking about for weeks. For those in doubt, even the VPN companies are saying the problem is the the OS "update." It's a bug.

Drix, Oct 11, 2024, 10:13 PM GMT+8:

Hello,

This is a follow-up on your issue of not being able to use iMessage on your Mac and/or iPhone when connected to the VPN.

We are pleased to let you know that we have confirmed that this issue is not present on iPhones. For MacOS 15 have added an option on the app "Allow Apple Services to bypass the VPN so iMessage and other apps work better" in Preferences > General > Network Lock. This is in response to changes made by Apple that are causing issues with apps like iMessage when the VPN is connected and Network Lock is enabled.

If you have previously turned off network lock before, please re-enable it again and check the box for "Allow Apple Services to bypass the VPN so iMessage and other apps work better". When checked, Apple Services traffic will not go through the VPN tunnel, and Apple push notifications will be sent outside of it. If you are having issues with iMessage and other apps while the VPN is connected, this should improve your experience with these services although full functionality might not be available.

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

Regards,

Drix

ExpressVPN Support

Tom Karches wrote:

I am not using a VPN, but having the problem with Messages not working on my MacBook Pro running 15.0.1. So it isn't always caused by running a VPN. I'll just send messages on my iPhone which isn't as convenient, but works.

On your iPhone, go to Settings/Apps/Messages (Settings/Messages for iPhone 17 or earlier), tap on Text Message Forwarding and make sure your Mac is checked.

Turned off my VPN (mullvad) and that resolved it. Must say I am deeply disappointed that a company which professes to care deeply about privacy can make such a blunder.

RodMo_

I was having the same issues, I use ExpressVPN too and saw your post. I updated the ExpressVPN software (I thought in the past that it would notify me of an update but I haven't seen any such notices, WTH?) and then unchecked "Stop all internet traffic if the VPN disconnects unexpectedly" as you said. THAT WORKED! Thank-you!

Macs Pain wrote:

I never thought the VPN could be the issue... Apple fix this ASAP, please.

There is nothing for Apple to fix. Regardless of what you thought, VPN can be the issue. Here’s the short answer:

When you install VPN it configures itself to the specific hardware, OS version and network that the phone 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.

Here’s the long answer→VPN: What you need to know - Apple Community

@Cthulhu Encrypt.me VPN. Everytime I stop securing the connection, iMessage will work appropriately, but would rather not have to kill the security to send messages. Seems silly.

An update on Private Internet Access VPN usage. As reported earlier, if I turn off the Kill Switch in PIA I can run my VPN and Messages will send the messages.

Not fixed unfortunately. In fact, I wasn't having any issues with Messages not sending or receiving until this morning, AFTER I upgraded to 15.0.1. I'm also on Mullvad, and disabling it made Messages work again. Split tunneling Messages in Mullvad does NOT work for me, btw. It's either use a VPN or use Messages - I can't do both.

This is infuriating.

I disconnected the VPN, quit messaging, and reopened messaging and it works!

I can't take the credit for this - credit goes to a Reddit user but it worked for me using Express VPN:

ExpressVPN was super quick to respond to me. I had to update my VPN software, as they just had a new release, and then there was a setting within the software that I needed to uncheck one box and it's working perfectly now with the VPN connected. Within the General > Network Lock section I had to uncheck "Stop all internet traffic if the VPN disconnects unexpectedly". Now that I have that off, I can connect to the VPN and iMessage syncs/sends flawlessly.