After updating my iPhone 15 pro max to ios 18 and my 2019 iMac to Sequoia messages no longer updates on my iMac. I can still read what was there before the updates but not afterwards. I also cannot send messages from my iMac. Messages is still working on iPhone.
iMac (2017 – 2020)
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.
Just spent a half hour with support who told me this is an issue and that they have to send a patch.
@hitbatsman are you using a VPN or proxy either on your MacBook or perhaps your router or network?
Yes, that worked for me as well, even without updating my ExpressVPN. Just had to trn off the Network Lock feature.
This did it for me. Upgraded ExpressVPN (from Version 11.59.0 (83862) to latest (11.6.0 etc.) and unchecked the box you referenced, and no more problems.
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.
There is clearly something broken with core OS-based VPN functionality and a variety of Apple cloud services. Notifications are blocked, and iMessage doesn't work as well as others that I can't recall at the moment. Considering how many businesses and enterprises require VPN I imagine this will get fixed in the next patch they release.
@gscottdesign I don't have ExpressVPN, but if they have anything that works like a config generator, try exporting a Wireguard config. The head to the App Store on your Mac, and download the WireGuard client (https://apps.apple.com/us/app/wireguard/id1451685025?mt=12).
Import that configuration in the app, and try and connect that way. For some reason the apps are not working, but if either you or the app adds a L2TP over TCP or WireGuard VPN interface, you may get Messages working again.
I'm afraid I don't have any ideas for the phone.
Good to know it's not just me. Can't send or receive any messages while connected to my VPN (Torguard).
This is a pretty massive bug. And I've seen posts of people mentioning this throughout the beta releases. C'mon Apple.
@joe pelline I've been working with TorGuard support - which is just terrific by the way. They talked me through a workaround that is very robust and does not involve exceptions or split tunneling, and it was pretty easy. Basically you the information they give you directly into the Network settings and everything works perfectly.
I suggest reaching out to them, and they will help. Unsure if they're going to rework their app, since as you probably know it gets refreshed for the Mac pretty infrequently. But they can get you up and running.
@Goose-bumps sorry, the threading makes it unclear which solution you've tried. So we can try and help, can you let us know:
It has a new setting called, "Apple services bypass". That implies to me that what ever changed in Sequoia was intentional by Apple and that Apple services traffic is no longer able to traverse a VPN tunnel. That's speculation on my part but based on what other people have posted regarding updated clients for other VPNs that seems to be the new normal for VPNs on macOS: you need to trust Apple and Apple traffic and trust that it is secure in transit from your router, ISP, DNS service, backbone, etc.
[Edited by Moderator]
I upgraded to 15.0.1 and still can't get the sync'ing to won't w/o unchecking the setting that turns my VPN off (Express VPN) if the VPN loses connectivity. This is what the VPN support put out w/ the workaround
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
Yes, I'm well aware that third-party security hacks always cause problems with macOS.
I've been using a VPN for far more than 10 years, good sir. And in Sequoia, I'm sorry to report the VPN is exposing networking bugs that also manifest without the VPN such as connection resets, ssh issues, firewall requirements to accept incoming connections where none were required before, and more.
I did have a VPN profile set up, but I rarely use it and I haven't used it.
The issue I reported with iMessage appeared to have worked itself out without me having to change a thing. A day or so later, it broke again... again, it fixed itself after a few hours. I'm happy to say that since then, I have been able to sync messages and forward text messages to green bubble people from my Mac again.
So, as I expected, my issue was not related to the OS or my configs. Hopefully, that helps folks relax until it either refreshes or Apple fixes it. Don't reinstall your OS for that kind of stuff as I explained in the original post.
-H
(In Apple I trust.)
macos Sequoia causing problems with messages on mac
