Is Cisco AnyConnect compatible with private relay?

Hi Murph,

I would just like to follow up on your response. I observe the exact same behavior. My iCloud Private Relay was working perfectly fine until I installed Cisco AnyConnect Secure Mobility Client. Shutting down the VPN did not fix iCloud Private Relay. The only fix was to completely uninstall Cisco AnyConnect Secure Mobility Client (for those wondering how, in the Applications folder, there will be a folder called Cisco and there are two separate uninstaller there), and restart my MBP.

For background, I'm using a 2021 MacBook Pro M1 Pro. This problem occurred on two totally distinct wireless networks. Restarting iCloud Private Relay did not resolve the issue.

I wanted to note a couple things:

Private Relay becomes unavailable before the installation is even complete. Every time I attempt to install AnyConnect, I have to go into System Preferences and manually allow the application to load. At this point in the installation, Private Relay is already disabled.

There appear to be three network interfaces, two of which is constantly running even when the VPN is not active. These interfaces are NOT established at the point when Private Relay becomes unavailable. The name of the interface is "Cisco AnyConnect Socket Filter". Two of them are not configurable. See the image below (the configurable interface is currently selected):

Additionally, one user allegedly resolved their iCloud Private Relay incompatibilities by manually editing the /etc/pf.conf file. In my /etc/pf.conf file, there are the following additional lines:

anchor "cisco.anyconnect.vpn"
anchor "com.apple/*"
load anchor "com.apple" from "/etc/pf.anchors/com.apple"

These lines WERE present at the moment when iCloud Private Relay became unavailable. Following the instructions in the linked post did not immediately resolve the issue. I will attempt to restart my computer and see if that resolves the problem.

Here's some food for thought: unless you're using a true VPN tunnel, such as between you and your employer, school or bank's servers, they are useless from a privacy standpoint.  Read these two articles: Public VPN's are anything but private and Former Malware Distributor Kape Technologies Now Owns ExpressVPN, CyberGhost, Private Internet Access, Zenmate, and a Collection of VPN “Review” Websites. 

Murph Sewall wrote:

Is AnyConnect likely to be the cause of the failure of private relay?

I don't know as I don't use a VPN nor Private Relay. You'd be in the best position to test it out by uninstalling AnyConnect and trying Private Relay.

I use AppCleaner when I want to delete an app to test it's affect on something. However, I don't delete the app, only its supporting files:

You will, however, have to enter any activation codes, passwords, etc that are required for reinstallation.

WARNING: If you use AppCleaner on an app that you have other apps from the same developer, like Adobe, you must be extremely careful checking all checkboxes and deleting.  Some for those files may support other apps from the same developer and deleting them can mess them up.  Adobe apps is a primary example. I know from experience.  For singular apps from a developer it's safe.

Okay, brief follow-up. Restarting my computer after editing the conf.pf file did not resolve the incompatibility. It looks like Cisco AnyConnect still didn't have an issue connecting to its VPN service, but it did automatically put the following line back in the conf.pf file when I started the VPN again after a restart.

anchor "cisco.anyconnect.vpn"

I am going to uninstall Cisco AnyConnect once more and restart. That should resolve my iCloud Private Relay problems, but if it does not, I will follow-up on this post.

I would love a resolution to this problem; so, I'm contributing all of my information here! Hopefully somebody smarter than I can put the pieces together... Happy to provide any more details about my setup in the troubleshooting process!

Matt