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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)
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.
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.
I cannot believe that this OS released (after public betas) with at least 2 glaring issues:
Used to be upgrading was a pleasant experience, but now the releases are broken.
Unacceptable.
Just spent a half hour with support who told me this is an issue and that they have to send a patch.
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.
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.
They better plan to send that patch as a MacOS Update...and yesterday speed.
Hey Apple! Stop acting like Boeing!!
Don't make me choose between iMessages and privacy!!
I will wait for a patch.
I know this has fixed it for some people, but not for any of us here. I spoke with Apple and three VPN vendors and waded through Wireshark captures. There is no DNS setting that permitted Messages to work for many of us here.
If you log out of Messages with no VPN, then connect the VPN, you cannot sign into Messages. Multiple other services like Sharing or FaceTime, are also broken. Setting shadow proxy and multi-hop VPNs does seem to allow you to reach Apple, but not to get a response.
I spoke with some very nice folks at Apple and at multiple VPN vendors, and in the end, Apple said there is no fix in the works, and that our best bet is to wipe drives, re-install Sonoma, and restore data from a Time Machine backup.
15.0.1 is not addressing the issue for me either with TorGuard nor PIA. The afore mentioned workarounds still work, but without them, Apple services are still not working with the latest version of both.
fherr wrote:
I already tried that with no success. I also rebooted the phone and the computer with no success. Sometimes my phone will see my iMac in the bluetooth settings but when I go to pair them the phone says the devices are not compatible then the phone doesn't recognize the iMac at all.
Verify your DNS is NOT Cloudflare DNS it is a known issue—
change it some other primary DNS
ex Google
ex OpenDNS
To be proactive you can file a bug report / submit your Apple Feedback here: Product Feedback - Apple
Top businesses are not upgrading to macOS Sequoia unless they have already tested everything in depth and released it to their managed fleet of Macs. Most defer the upgrades for 90 days because whenever Apple upgrades the OS they change the security model in some way that causes breaking changes in 3rd party software and hardware. This has happened most every year since Sierra. At this point, we don't trust Apple with a dot zero release and we tend to wait for 2-3 patches before we deep dive into getting a new macOS working.
I have three VPN style connections and they all work as expected. VyprVPN, OpenVPN, and Tailscale all work fine for me.
I would think that features such as Private Relay, etc. may be part of the problem people using VPN might encounter. Try turning these iCloud features OFF.
Apple did indeed make changes to the macOS network stack in Sequoia. Several VPN vendors have problems an update on their part will likely fix.
It is possible the VPN software interfered with macOS during the installation of Sequoia. Try booting into Safe Mode and re-installing macOS over the top of your existing system. Start up your Mac in safe mode - Apple Support, open Terminal -> softwareupdate --fetch-full-installer --full-installer-version 15.0.1 then re-install via /Applications/Install macOS Sequoia.
Two reports:
iMessages problems after updating to macOS Sequoia (15.x)?
That's most probably due to the VPN problems and while I give the directions here for Cloudflare VPN, you can whitelist the same IP addresses in your own VPN provider
macOS Sequoia (15.x) x Apple Push Notifications Service (APNs) x Cloudflare Zero Trust (Warp)
In Zero Trust, go to Settings > WARP Client.
Under Device settings, locate the device profile you would like to modify and select Configure.
Scroll down to Split Tunnels.
Under Split Tunnels, choose a mode:
Exclude IPs and domains — (Default) All traffic will be sent to Cloudflare Gateway except for the IPs and domains you specify.
If you can't allow access to the entire 17.0.0.0/8 address block, open access via the same ports to these network ranges on IPv4 or IPv6:
IPv4
IPv6
2620:149:a44::/48
2403:300:a42::/48
2403:300:a51::/48
2a01:b740:a42::/48
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]
macos Sequoia causing problems with messages on mac
