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.
I've not tried ExpressVPN, but with PIA who offers a split-tunnel and a setting for Apple services, it still does not work for me. I am able to send SMS's, but I don't receive notifications or messages. I know the moderators do not like any mention of unreleased software, but it does appear a fix is incoming from Apple hopefully. Hang in there, everyone.
Wow, thank you. ExpressVPN comes through AGAIN! That fixed it.
A friend of mine turned me on to the Split Tunnel and and bypass messages and now I can send messages Receiving is another issue
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.
Exact same problem on the same MBP Model. Turning off my VPN is not an option. The entire reason I use messages is its better security vs raw text. And I use a VPN for the same reasons.
[Edited by Moderator]
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.
MarkyMarc43 wrote:
• I cannot believe that this OS released (after public betas) with at least 2 glaring issues:
No messages can be sent or received from Mac
• Apple Watch (series 6) cannot unlock my Mac - or even sync with it for that matter.
Used to be upgrading was a pleasant experience, but now the releases are broken.
Unacceptable.
I don't have an Apple Watch, but I have had zero problems with Messages. Works better than before.
I strongly advise against disabling the network kill switch with your VPN. One little hiccup and your data will go out without the VPN protection with no warning to you. Also that setting should have no bearing on the traffic while the VPN is connected.
It looks like if you manually add L2TP interfaces to the Network settings in macOS, the VPN generally works with Apple services. But no VPN app works. Sounds like ExpressVPN found a workaround, which is great!
I strongly advise against disabling the network kill switch with your VPN. One little hiccup and your data will go out without the VPN protection with no warning to you. Also that setting should have no bearing on the traffic while the VPN is connected.
What protection is that? The "protection" that funnels all of your network traffic into a single company's database so they can sell you off in one neat package?
It definitely does. With the kill switch off, if your VPN drops even for a few seconds, all traffic will go out as if you had no VPN until the VPN reconnects. And in my tests of PIA, that happens often. Normally you would not notice, but I did a Wireshark (network monitoring tool) capture and saw a lot of traffic go out sans VPN over the course of an hour with the VPN was on.
If you follow the steps I outlined and get a VPN configured in the System Settings instead of in the VPN vendor's app, Messages does not go around the VPN, so that's the good news. The bad news is that there is no kill switch setting. I saw my VPN drop, and Messages (TCP port 5223) leak many times. So as you say, what else is leaking out? When I just looked at all non-VPN traffic, the answer was - a lot. When I used the VPN app, whatever routing magic they do seems to address that.
So ... this is definitely not a perfect nor a permanent workaround. I would stay off the McDonald's Wi-Fi for now :-)
@NittanyRyan. Ug, I am very sorry to hear that. This update has been so frustrating. There is a thread re Mullvad at https://github.com/mullvad/mullvadvpn-app/issues/6521#issuecomment-2368869711 that may be interesting to you. It would seem to imply you might be experiencing yet another issue if using the VPN service is not helping.
Interesting read over on pcmag.com with the headline 5 Ways macOS Sequoia Is Worse Than Windows.
None of that is a problem for me. The window tiling is hilarious as I have never needed to set all of my windows to a fixed size. Different jobs require different windows in different sizes and places. I turned that all off on my Windows work computer.
Seems like a lot of users are really angry with Apple over a lot of issues.
I don't see a whole lot of that, here. Most upgrades have more complaints across many issues. The biggest one I see are all of these incompatible so-called "VPN" apps. Maybe it will help more users find out they are being scammed and get rid of them.
I have tried the OpenVPN with profiles from two vendors and no, it does not work. Like most apps, it does not add a profile into your VPN settings. I also spent a good bit of time both on the phone and in chats with Apple. I would not expect them to chime in a forum here, but they are definitely aware of the issue. They have only 10 bug reports that I can see on this topic, so perhaps they don't see it as a big issue. I have no idea - but a fix from Apple would certainly make life simpler for everyone.
See if this helps...
Likely the problem is Apple's bizarre choice of display order, the default isn't normal.
Go here...
Cthulhu’s Profile - Apple Community
Click on Edit Profile &settings near the top at the right, scroll down until you see other preferences>Default Sort Order, chose Oldest.:)
@hitbatsman I searched on the encrypt.me site but I could not find instructions to export the profile, and that's the way to get it working. You have to add your VPN into the macOS network settings directly. I'm afraid I don't have encrypt.me so maybe someone else who does could chime in.
macos Sequoia causing problems with messages on mac
