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.
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
Just wanted to say thanks for the helpful advice. I use PIA and turning it off works. Not a great solution though it works for now and hopefully Apple will fix. Would never have figured out it was the VPN except for this community.
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.
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!
A new version of Mac OS, Sequoia 15.0.1 (24A348), has been released. It it purported to address the following.
According to Apple's release notes, macOS Sequoia 15.0.1 fixes a bug that could cause the Messages app to crash when a message with a shared Apple Watch face was sent, and it improves third-party software compatibility. Apple's release notes for the update are below.
macOS 15.0.1 release (24A348) This update provides important bug fixes for your Mac including:
- Messages may unexpectedly quit when replying to a message with a shared Apple Watch face
- Improves compatibility with third-party security software
Some features may not be available for all regions or on all Apple devices.
I installed the new version of Express VPN with the Allow Apples Services to Bypass the VPN feature. So far so good, mostly. iMessages works with VPN on. But now I can't log in to this chat without turning off the VPN. I wonder if Apple has made it's site inaccessible to VPN access. Anyone else having that problem?
PS--I understand the new feature is just a workaround not a solution, but it's better than the alternative til Apple fixes it's OS.
@MartinJMannion If you are on a home or work network behind a firewall or Wi-Fi router, try turning off the firewall in your network settings on your Mini and see if that makes a difference. It was causing me trouble in the Terminal and with Xcode as well as Messages on my M2 (this is another bug unrelated to the VPN issue).
I was having the same problem with PIA vpn. I turned off the kill switch and now it works. hoping a fix from Apple will come soon.
"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."
What a go screw yourself "solution".
Can confirm this seems to be fixed in 15.1
This worked for me, too.
In Express VPN, from the Hamburger menu / Preferences / General / Network Lock / deselect "Stop all internet traffic…"
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
Two reports:
For PIA VPN they had me whitelist apple services. Not sure if that degrades the function in any way:
To fix this issue, we will need to add an IP address to the Split-Tunnel, which in turn will whitelist all ¨Apple services¨. That means that those requests (i.e. iMessages) will go outside the VPN.
To proceed, please do the following:
fherr wrote:
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.
If you are using a VPN disable it and compare your results.
macos Sequoia causing problems with messages on mac
