Posted: 11/5/2025 1:41:23 AM EDT
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I've been using this setup for a couple years now while traveling... My home router has embedded OpenVPN, and I have a Raspberry Pi that is running Wireguard. The OpenVPN is a failsafe in case something happens to the Pi. I've been doing some other tweaking on the Pi, adding some cloud apps, etc. I went to visit someone and thought I'd take my MacBook along to verify everything else worked properly. BUT... suddenly I couldn't connect to the VPNs! Either of them. OpenVPN gives a connection error right away. Wireguard says it connects, but doesn't pass anything through at all. I can't access my remote computers, or even get web pages rendered. I've been trying to troubleshoot this for a couple days now. I'm starting to think it's a MacOS 26 issue. I have the EXACT same config files for both OpenVPN and WireGuard on my iPhone, and I can connect to my home network while on cellular and can even browse local web pages, etc. I rely on this connectivity for my job... I travel a lot and I have a work desktop back at home that I remote into. @right_rudder ... have you seen anything like this at all in your bug list backlog? I think I've pretty much exhausted all the options to try to fix this any other way, and since the same file works on iOS but not MacOS 26, I'm thinking that's a good smell test towards there being something wrong. |
| Funny you brought this up. I posted earlier about having problems with the PIA VPN app not connecting. I keep having to delete the app and reinstall to get it to work. Even then it’s very slow. The next day I’ll have to do it again. This started right after I updated to OS 26. I’m not a big enough techie to figure it out. |
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Take a look at TailScale. I've been using for quite a while and it works wonderfully. I use at a poor man's SASE so I can access resources from a specific IP address regardless of where I'm at. I connect to my TailNet, pivot though the exit node at my house, and I'm ready to go. |
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Originally Posted By ScubaDachshund: Funny you brought this up. I posted earlier about having problems with the PIA VPN app not connecting. I keep having to delete the app and reinstall to get it to work. Even then it’s very slow. The next day I’ll have to do it again. This started right after I updated to OS 26. I’m not a big enough techie to figure it out. Update: Still doesn’t work. Contacted PIA support. They suggested changing the settings (which I had told them I can’t access) or downloading the latest version of PIA app ( which I had told them I had already done). I reiterated those points in my response. |
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Originally Posted By GloriusMark: Take a look at TailScale. I've been using for quite a while and it works wonderfully. I use at a poor man's SASE so I can access resources from a specific IP address regardless of where I'm at. I connect to my TailNet, pivot though the exit node at my house, and I'm ready to go. It was a macOS bug. After I got the latest update, everything worked as it should. My primary VPN is WireGuard (which is what your TailScale uses deep down, mine just doesn't have the extra overhead or third party involvement). The home server is running on my Raspberry Pi. For redundancy, I have OpenVPN set up on my router... if my RPi goes down for some reason, as long as my internet is on at my home, I can get in with that. But it's not as fast as WireGuard. I was using the OpenVPN client, but I guess it is pretty outdated now... I switched to Tunnelblick as my OpenVPN client. When I was messing around with trying to fix my VPN issue (before I realized it was actually an Apple issue), I added a THIRD redundancy... ZeroTier. Really neat; it's not actually a VPN, but it will connect my to my home to do what I need to do exactly the same. I set up my ZeroTier on my MacBook, and another on my RPi, which I use as a gateway to my network. You can't get any simpler than than their setup... but the throughput still isn't as fast as WireGuard. |