A minimum of 5 time the Siri app stopped being able to connect. Restarting was the only recourse.

AgingKeeper wrote:

- Network: Ethernet (primary) using Express VPN.

The root cause of this persistent "unable to connect" error is a routing conflict between ExpressVPN and the network configuration framework in macOS 27.

When you connect via Ethernet while ExpressVPN is active —especially with Wi-Fi enabled simultaneously— macOS handles encrypted packets through network extension helpers. Over time, or following small drops in connectivity, the helper processes responsible for the VPN tunnel drop or misroute Apple's iCloud/Siri API traffic. Toggling Siri doesn't work because the underlying routing tables are fundamentally locked up until a hard reboot.

3rd party ‘protection’ software includes:

• Cleaners (software claiming to automatically free up space)
• Optimizers (software claiming to make your Mac run faster)
• Antivirus software
• VPN software (unless provided by a school/employer to enable access to internal resources from a remote location)

Such 3rd party system ‘helpers’, ‘cleaners’ and ‘protectors’ do more harm than good. In fact, such products are completely unnecessary for macOS and the only ‘good’ (if you want to call it that) they do is to put money in the developers’ pockets. Cleaners and protectors cause compatibility issues, often after macOS updates. Commercial VPNs claim to hide your browsing activity from websites, and while that may be true those VPN providers just sell your browsing data to others.

For the user, all of these types of software offer only harm…and if that is limited to harm to your bank account, then count yourself lucky. If you have installed such software, follow the developer’s instructions to completely uninstall it (note that some developers fail to provide instructions and their software installs can be pervasive, meaning the only way to truly remove it is to erase your Mac, reinstall macOS then restore your user files from a backup).

According to AI (which I trust as far as I can throw in many cases), ExpressVPN contains a setting specifically designed to prevent this behavior by routing Apple's telemetry and core services (like Siri and iCloud) outside the encrypted tunnel.

• Open the ExpressVPN app.
• Click the Menu icon (three lines) > Preferences.
• Go to the General tab.
• Locate and check the box for "Allow Apple Services to bypass the VPN".

If true, perhaps that will solve this particular issue. It won't solve the bigger issue of the VPN not doing what you think it's doing.

AgingKeeper wrote:

Getting rid of the VPN would provide useful information but it is simply correlation not causation. Hence being able to point to something quantifiable is perhaps a more reasoned approach.

I had to use a VPN for years, provided by my employer before and during and after the pandemic, to enable access to a secure and closed company network from off site (e.g. home office, or while on travel). That VPN was professionally configured by Cisco in collaboration with my employer, it was a custom set up. There were MANY issues that users faced when connected through the VPN, all kinds of conflicts and oddities. Whenever we did not have to, we always turned it off. The employer changed VPNs at least half a dozen times over the years in an effort to minimize those conflicts, which occurred both on Macs and PCs. Also, the VPN slowed down our internet speeds by about a factor of 2. But we also found that even with the VPN turned off, its installation even when in the "off" state resulted in some conflicts.

Even when "off," the VPN being installed prevented us from using Notes with iCloud, Siri, and Apple News. Oddly, we still could use Messages in iCloud, however, as well as iPhotos in iCloud. The VPN was intrusive thus in unpredictable ways that sometimes did not even make sense.

In your case, based on my experience, I would suggest AS A TROUBLESHOOTING STEP, that you completely uninstall and remove the VPN. Then test to see if the problem is gone. If it is gone, you have your answer. If it is still there, you can always simply reinstall your VPN. I agree with the others that users should not be installing and using VPNs unless their school or employer mandates it (the government agency we had contracts with mandated it), but I leave that decision up to you. What I am suggesting is a simple non-emotional engineering troubleshooting step to see if it fixes your problem.

I think there could well be other things (than the VPN) causing this for you, but you won't know until you try removing (uninstalling it) it completely. One reason I think the problem may persist is that Siri AI may still be a beta install of sorts and those always have quirks. I did disable the Siri beta on my Apple Watch and iPhone because it caused some instances when Siri did not function as expected. You might be experiencing that on your Mac, independent of the VPN possibility.

So I would start with completely removing the VPN, and simply put it back if that is not the answer. Next I would disable the new AI beta aspect of Siri.

AgingKeeper wrote:

First, of course I understand Siri is a beta. Even if it were not it is a piece of software and having been made by people flawed in some manner. My original question was intended to see if others have had this issue, nothing else.

Polls and surveys are prohibited here by the Apple Support Community Terms of Use.

Consider yourself lucky the moderators have not completely deleted your post. Yet.

So far all I have gotten in in this response are statements that I am supposed to assume are correct along with comments like telling my that what I am doing is counter-productive, and not legitimate (talk about self righteous).

As I indicated in my earlier response to neuroanatomist, information that would allow me to verify for myself that the VPN is the cause of this issue would be helpful.

That's easy. Get rid of the VPN. Don't just turn it off, remove it entirely. If the problem goes away, the problem is being caused by the VPN.

And there is NO LEGITIMATE reason to use a VPN to access the Internet. It does not do what you think it does.

Unless you're using a true VPN tunnel, such as between you and your employer's, school's or bank's servers, they provide false security from a privacy standpoint.  Read these articles:  Pubic VPN's are anything but private and Security Risks: The Dangers of Using Free VPNs (eccu.edu).    

Additionally a new study ("Apple Offers Apps With Ties to Chinese Military”) is specifically about VPN apps in Apple’s App Store.

I recommend uninstalling the VPN according to the developer's instructions. Then you can check to see if you've removed all of the supporting files by downloading and running the shareware app Find Any File  to search for any files with the application's or the developer's name in the file name.  For the XXXX files you'd do the following search(es): 

1 - Name contains  vpn

2 - Name contains express

Any files that are found can be dragged from the search results window to the Desktop or Trash bin in the Dock for deletion.

FAF can search areas that Spotlight can't like invisible folders, system folders and packages.  

If you get warnings that the file can't be deleted because it is in use or used by another app boot into Safe Mode according to How to use safe mode on your Mac, run Find Any File again and delete from there.

Note:  if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode.  This makes it act as a wired keyboard as will assure a successful boot into Safe Mode.

I share your feeling about AI and your feeling about AI seem to be justified for this issue. In v14.3 of the expressVPN app for macOS 27 there is no longer a General Tab and I can find no setting to Allow Apple Services to bypass the VPN. The only thing I can see that might provide this capability is Split Tunneling which allows users to bypass the VPN for specific apps. I am not sure I am confident enough in knowing which apps on which to apply this feature. The Siri feature for sure but are there other underlying system services that would also need this treatment.

So is the issue on Apple's side of things or on the 3'rd party side of things? How would someone verify what is happening to sort this out? Seems to me that Apple's software should be able to work well with VPNs as there are a significant number of users employing VPNs for business, personal use and tools like Tailscale (which I gather uses VPNs as well).

FYI, I am connecting using both ethernet & wifi because Apple seems to need this for something(s) they are doing. My primary connection is ethernet.

In addition I do not use cleaners, optimizers, or anti-virus software. I am also not sure that all VPN providers are selling browser data (Express VPN has been independently audited to support their claims as have several other VPN providers). I have had issues with ExpressVPN's exit points being blocked by websites. So I am now looking at Cloudflare's WARP/1.1.1.1 service. Seems to alleviate the blocking issues and it too claims to not keep user data.

The problem is your VPN.

Using a VPN to access the Internet is completely counterproductive. It does absolutely nothing to protect your privacy or secure your data.

There is no legitimate reason to use a VPN other than to connect to a secure private network such as your employer or school so you can access resources on their network.

Get rid of the VPN.

Aside from that, you need to keep in mind that Siri AI is still in beta. You can expect problems. That's the nature of Betas.

First, of course I understand Siri is a beta. Even if it were not it is a piece of software and having been made by people flawed in some manner. My original question was intended to see if others have had this issue, nothing else.

So far all I have gotten in in this response are statements that I am supposed to assume are correct along with comments like telling my that what I am doing is counter-productive, and not legitimate (talk about self righteous).

As I indicated in my earlier response to neuroanatomist, information that would allow me to verify for myself that the VPN is the cause of this issue would be helpful.

If describing an issue and receiving help from community members is now considered a poll or survey than my use of the community has not been correct for quite a long time. If the moderators want to delete my posts they are welcome to do so of course.

Getting rid of the VPN would provide useful information but it is simply correlation not causation. Hence being able to point to something quantifiable is perhaps a more reasoned approach.

AgingKeeper wrote:

If describing an issue and receiving help from community members is now considered a poll or survey than my use of the community has not been correct for quite a long time. If the moderators want to delete my posts they are welcome to do so of course.

You said "My original question was intended to see if others have had this issue, nothing else."

There is nothing in that statement to indicate you were attempting to receive "help" with a technical problem at all.

Getting rid of the VPN would provide useful information but it is simply correlation not causation. Hence being able to point to something quantifiable is perhaps a more reasoned approach.

Good luck with that. If you are unwilling to try the simplest, most logical step in troubleshooting the problem, you are unlikely to solve it at all.

You said "My original question was intended to see if others have had this issue, nothing else." There is nothing in that statement to indicate you were attempting to receive "help" with a technical problem at all.

My experience in this community is that other people who have had similar technical issues, typically provide answers that might help resolve issues I am experiencing. So attempting to see if other community members have had similar issues is the way I have experienced the community providing help. Most responses have been quite helpful.

The issue I am experiencing happens randomly, I can certainly get rid of the VPN and the problem may very well go away or it may not. Of course the problem could be with Siri or macOS that goes away with macOS 27.3. Trying to identify something I can use to repeatedly observe the issue is what I had hoped I would be able to learn. Neuroanatomist provided some of those insights, so I am looking into those.

You attempting to tell me that I am stupid for using a VPN, and that my use of it is NOT LEGITIMATE is completely unnecessary. You obviously have a need to make the point that your knowledge is amazing on this topic. So I bow down to your superior intellect. Luckily your definition of legitimacy is confined to your world.

Systematically eliminating possible causes of a problem to help identify the cause is perfectly reasonable and logical.

As for your use of a VPN being "legitimate", please explain your reasons for using a VPN to access the Internet.

If you believe it is somehow protecting your privacy or securing your communications, you are mistaken. It is doing exactly the opposite.

If you are using it so that you can access content that is restricted to regions other than your own by making you appear to be located elsewhere, you are violating copyright law and potentially committing a criminal act.

Anyone using one to bypass restrictive government controls, is potentially committing a crime, no matter how much anyone may sympathize with that reasoning.

VPNs have become ubiquitous because the uneducated public buys into the FUD spouted by the VPN vendors and the so called security industry. If you're paying for a VPN service to access the internet, the best case scenario is that all it does is lighten your wallet. If you're using a free service, you can be assured that your data is the product they sell to make money.

The ONLY legitimate use for a VPN is to connect securely to a private network.

That definition is not confined to "my world" unless you are referring to the world of career IT professionals.

I've been in this business since well before the Internet became public. I believe Apple's top of the line Mac at the time was the Macintosh IIx.

Of course, you're welcome to reject logic and continue using what is at best a useless tool and at worst a service that could seriously compromise your data. That's entirely up to you.

If you would like to explain what you feel is a 'legitimate' use of a VPN, I'm all ears.