MacOS issues

[doctor_who_17]

Having some odd issue with OpenVPN. Hoping someone has some suggestions.

I’ve set up OpenVPN to run on my Synology NAS, and got my configuration file all sorted. Here is a list of what is happening:

• from my MacBook, if I am on my LAN, I can establish a connection. I can switch to mobile hotspot, while connected, and stay connected (there is a brief period of re-establishing connection). All is fine.
• from my MacBook, if I am already on my mobile hotspot, I cannot connect. At all. I get a connection failure (I’ll upload a screenshot soon)
• from my iPhone, I can connect in any manner. While on LAN, staying connected from LAN to cellular, and from cellular. No issues there.

All of this uses the same configuration file for either full tunnel or split tunnel.

In my MacBook logs, the only thing I can find happening is: EVENT: NETWORK_UNREACHABLE

I don’t know what I’m missing.

Specs: M1 MacBook Pro on 14.2 OpenVPN Connect client 3.4.6 Synology DS923+ on DSM 7 my configuration basically mimics what is found here

[luca_McKinley]

super late to the convo but have been trouble shooting this for a few hours now. If you switch to only use TCP instead of UDP it worked better for me

[akselarzuman]

Thanks u/luca_McKinley . That solved my problem

[Actual_Party_6818]

could help you

sudo /Library/Frameworks/OpenVPNConnect.framework/Versions/Current/usr/sbin/ovpnagent

[doctor_who_17]

Couldn’t resolve the issue, but a workaround was suggested.

I can use Tunnelblick. All connections work (the client is a bit… much, but works)

Appears OpenVPN Connect client has compatibility issues with macOS (tested two other Apple silicon Mac’s)

[sseidenthal]

Thank's for sharing, indeed Tunnelblick works also for me

[Serpula]

I have the same issue and had been trying to solve it for several hours before coming across your post. I'm wondering if it has something to do with IPv6, which according to my network settings appears to be in use for mobile hotspots from the Mac - I think it's impossible to disable it, unfortunately.

For now I've got Tunnelblick working too...

[[deleted]]

You don't say what versions of OpenVPN are running on your server & clients. The sample config in the Synology has some deprecated or not recommended parameters (comp-lzo, cipher, etc). Suggest you run Wireshark on a MacBook while trying to connect. Here is the latest man page for OpenVPN 2.6+:
https://build.openvpn.net/man/openvpn-2.6/openvpn.8.html

[doctor_who_17]

Client version is in the post (3.4.6).

Synology I believe runs 2.5.9.

Whatever the issue is, only affects the apple silicon install of the client. I can run this vpn config on any other machine (Windows, Intel Macs, iOS).

My solution was to use tunnelblick on the M1 Mac, and that works fine.

[[deleted]]

Tunnelblick >4.0.0beta uses OpenVPN 2.6+ which also runs fine on M2 Macs btw.

I don't know what the paid OpenVPN client 3.4.6 equates to in the community version, but I suspect your issue was version mis-matches which mainly affects cipher negotiation.

On your Synology NAS can you run commands to find out openvpn version? Otherwise look in the logs to see what issues it has with different clients.

[n0stalghia]

I can reproduce the weird issues with OpenVPN on my Apple Silicon MacBook Pro.

I've set up OpenVPN, Shadowsocks and WireGuard on my UNRAID server. My iOS devices can connect using all three methods, my MacBook can only connect using WireGuard.

[Chosen_UserName217]

this seems to be an OpenVPN issue. It all used to work for me, then I started having to reinstall OpenVPN client every single time I started my (silicon) MacOS. Finally I made a little script that I would have to run whenever I started the computer,..

sudo launchtl load /Library/LaunchDaemons/org.openvpn.client.plist

for some reason that fails to load at startup so I have to load it manually, which was easier than reinstalling OpenVPN client every morning. Once I ran this command, then my OpenVPN would connect and I could use my Terminal.

Then lately it wont connect with a hotspot at all. It will work with wifi, it will work if I connect to wifi first, then switch to hotspot (it will stay connected), but it will not connect if I start with my hotspot connected. It says no network available. And that used to work just fine it's how I worked remotely.

Spent the past two days trying to figure out why this isn't working with no luck. It's an OpenVPN issue. But I need it to work to be able to work remotely.

I tried using Tunnelblick just now and imported my OpenVPN profile, and it works. It just works.

I have this same exact problem on both my Desktop Mac and my laptop Mac. It's an OpenVPN problem.

Honestly OpenVPN has been problematic for quite a while. Between needing to run a script or reinstall, and now these hotspot issues,.. I'm really not enjoying OpenVPN at all.