VPN / DNS Issues With macOS Ventura

After upgrading MacBook Air M1 to Ventura I noticed that several of our internal business sites, RDP connections and Network SMB folders which require a VPN to access would not resolve, even after a successful VPN connection. and would only work via their respective IP addresses


Usual troubleshooting including...


  • Home router reboots
  • Mac reboots
  • Re-creating VPN connection
  • Different browsers
  • Different VPN account
  • macOS DNS cache clear
  • Switching to a mobile data (tethered) connection and then connecting to the vpn did not resolve


In desperation had to resort to manually editing the HOSTS file

sudo nano /etc/hosts


... which allowed the respective sites, folders and connections to resolve.

It's clear that Apple devs have broken DNS networking stuff which worked in Monterey and before.


Users should not have to manually edit the macOS HOSTS file to use DNS names whilst connected to a VPN in Ventura

MacBook Air 13″, macOS 13.0

Posted on Oct 26, 2022 5:48 PM

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Question marked as Top-ranking reply

Posted on Apr 6, 2023 4:43 PM

Hi,

I have been having this problem also but I just solved it. I actually only joined to post the solution


Indeed the /etc/resolv.conf is over-written props to the user who pointed that out on page 3). For me it was overwritten with an internal 10.x address so obviously DNS was failing.


What is causing the overwrite is after upgrading apple turns on by default limit ip tracking.


01) Go to settings

02) Go to networks

03) Click details next to the network name In my case my wireless

04) Turn off limit ip tracking

05) Try your vpn again


That one thing fixed the automatic overwriting of the conf file.


I work in cloud security arch and while I am a big believer in secure defaults it is obnoxious to roll something like that out breaking people's vpns without some kind of warning.


Good luck to everyone!

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89 replies

Dec 16, 2022 5:24 AM in response to f1r3s4l3

f1r3s4l3 wrote:

Because some people don't use VPN for privacy reasons, but because they access a company network through it, and probably only for specific addresses, so you want to use the public DNS for everything else.

But this is a user-to-user support forum for Apple’s consumer products. No one here knows anything about MDM, Jamf, or anything enterprise related. Enterprise users have their own dedicated, paid support staff. If they can’t resolve the issue, they can just call their Apple reps on the phone.


If there is a problem, you’ve found the best place to hide from the people whose job it is to fix those problems for you.

Dec 16, 2022 7:38 AM in response to etresoft

To put it very simply: This is a very normal feature, and it worked in 12.x but does not correctly in 13.x.

And as it (at leas in my case) only happens after the device went to sleep, it would seem common sense that it's not working as designed.


So IMHO it's quite irrelevant whether we're using this to connect to our VPN at home but still want a public DNS for whatever reasons, or if we're stumbling upon this issue in an enterprise environment.

Apple should be grateful that we're bringing this to the public and thus helping to improve their products, but if they prefer to not talk about any potential issues, well...


I find it quite funny that every time someone finds a bug or something like that in an Apple product, someone with thousands of points jumps in to defend Apple. And I wonder if this comment will even make it to the forum, as my last try at a reply was censored for reasons unknown.

Dec 16, 2022 10:55 AM in response to f1r3s4l3

f1r3s4l3 wrote:

Apple should be grateful that we're bringing this to the public and thus helping to improve their products, but if they prefer to not talk about any potential issues, well...

Why should Apple be grateful when people experience problems and then don't report them? As I said above, this is a user-to-user support forum for Apple’s consumer products. Apple isn't here.


You are describing a problem that sounds like the opposite of what you describe. If I have a VPN connected and my DNS requests go out to an open DNS server, that's a critical, mission-failure of the VPN. However, I'm not even going to bother testing this because I don't want Google tracking my DNS requests, whether I'm using a VPN or not.


I find it quite funny that every time someone finds a bug or something like that in an Apple product, someone with thousands of points jumps in to defend Apple.

There is lots of misinformation being repeated on the internet. The people here are focused on facts and solving problems. If there is a problem with an Apple product, we will say so and offer workarounds. But in the vast majority of cases, the problem is with some 3rd party product.

Dec 28, 2022 1:13 AM in response to f1r3s4l3

I've just stumbled on this post as our internal DNS does not want to work any more with Ventura, we have always had problems, but now the normal fixes don't help... I'm glad I found this as I know now we're not alone, I'm going to look in to raising this with Apple as we should have a rep, if they ever give me anything useful back I will try to add it here (but I won't hold my breath)

Jan 26, 2023 2:08 AM in response to hamacardo

And one more piece of information: I've just tried contacting Apple support. As soon as they heard the problem is only visible when connected to the VPN, they said it's not something they can help me with; to quote them: "if you disconnect from the VPN and everything works fine, there's nothing we can do for you".


Way to go Apple!


Advisor suggested contacting my VPN provider (which is pointless because tunnel works great and older MacOS or any other OSes work great) and trying my luck on developer.apple.com

I guess I'll do the latter on the off chance.

Feb 1, 2023 2:29 AM in response to weakcamelsm

You probably missed the most important point:

Apple does not make any mistakes. Full stop.

If it doesn't work, you're not using it correctly.


<sarcasm off> ;)


That's the reason we've dumped our M1 Max Macs and are now working with Linux on HP hardware.

We've spent too many hours finding workarounds for not-bugs in MacOS or hardware failures lately, it's getting too expensive.

Feb 1, 2023 3:48 AM in response to f1r3s4l3

Intersting. Hardware seems fine I think. Not many software issues for me either. But I do agree with you that some ”high level” people here seem to think it’s never a problem on Apple’s side, which in this case it seems pretty clear to be.


I will investigate more and report it to Apple via other channels. Maybe macOS 13.3 has something in store when it comes to this…

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VPN / DNS Issues With macOS Ventura

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