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hamacardo Author

Level 1

31 points

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

Top-ranking reply

f1r3s4l3

Level 1

30 points

Posted on Dec 16, 2022 7:38 AM

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.

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89 replies

Jan 11, 2023 8:20 AM in response to hamacardo

had a ton of vpn and internet issues in general on ventura -- turns out i unintentionally had iCloud private relay enabled. disabling this sorted everything out.

XDM

Level 1

12 points

Jan 17, 2023 3:07 PM in response to thomaspage

I can confirm Private Relay is at play. DNS resolution would fail on private DNS accessed through VPN, ie internal business web sites. Turned off Private Relay, reconnected VPN, DNS success.

XDM

Level 1

12 points

Jan 17, 2023 3:38 PM in response to XDM

...And since Private Relay only works with Safari, I can also confirm that DNS resolution succeeds using Chrome through VPN (fails with Safari w/ Private Relay on & VPN).

Jan 18, 2023 1:04 AM in response to XDM

This must be just your specific use case.

In my case, both basic tools (like e.g. ssh/ping) and Chrome browser don't resolve properly despite nslookup returning the correct values.

Jan 25, 2023 10:41 AM in response to hamacardo

I just tried upgrade to 13.2 Ventura. Sadly, no improvement at all - standard tooling still doesn't resolve addresses from the internal DNS (despite nslookup returning correct IPs).

Mar 2, 2023 7:59 AM in response to StockerRumbles

Aha, interesting! Let me know how it goes. I can at least say that there is no problem like this with Jamf and Monterey.

vontomke

Level 1

8 points

Mar 8, 2023 1:26 AM in response to hamacardo

I'm not using JAMF and still have this issue.

Mar 21, 2023 11:41 AM in response to OverweightBatman

I'm encountering the issue in 13.2, so I don't think it has been completely fixed.

Mar 22, 2023 2:41 AM in response to owendelong

No, it's not been fixed. I'm on 13.2.1 and still facing the same issue. Even my previous workaround of overriding resolver in /etc/resolver/<domain> config stopped working.

Mar 31, 2023 9:12 AM in response to weakcamelsm

Yes, it's sad. I'm hoping for the 13.4 release. Have an open ticket with Apple and have provided some info and also got a response back, so we'll see what goes during the beta testing...

mprush12

Level 1

8 points

Mar 31, 2023 9:22 AM in response to star-affinity

What was Apple's response? Are they aware of the issue? Did they say they were planning on addressing it?

mprush12

Level 1

8 points

Mar 31, 2023 12:45 PM in response to weakcamelsm

I spoke to Apple per our Enterprise Support Agreement, and they said they were not aware of an issue but they are looking into it now.

Jun 29, 2023 4:50 PM in response to nvssm

Frankly, your issue is probably best addressed by contacting Apple support or going to a Genius Bar.

NickTK

Level 1

9 points

Aug 17, 2023 5:37 AM in response to hamacardo

The same problem, macOS 13.5, no one checked by chance, maybe they fixed it in Sonoma?

VPN / DNS Issues With macOS Ventura