Since Apple claims that Cisco VPN is natively supported, and it is explained in detail here, my guess would be a VPN configuration issue or mismatch. It may be a matter of matching the Remote Access VPN setup to the OSX client, instead of the other way around.

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Install and Run the Cisco AnyConnect client for VPN Mar 31, 2020

How do I configure the OS X integrated IPSec VPN client

Jun 15, 2020 · This article shows you how to download and install the Cisco AnyConnect Secure Mobility Client version 4.3 on a Mac Computer. This article is applicable only to Cisco Business products that includes the RV34x series routers and not Enterprise products. Introduction. AnyConnect Secure Mobility Client is a modular endpoint software product. As an alternative to downloading the Cisco VPN client for Mac OS X, you can also use the built in IPSec version found on your machine. This might be more convenient for those who wish to avoid installing additional software. Simple to deploy and operate, the Cisco VPN Client enables customers to establish secure, end-to-end encrypted tunnels to Cisco remote access VPN devices Free Cisco Systems Mac OS X 10.4 Intel Step 1 Install Cisco anyconnect VPN client for Mac OS X. Double click on AnyConnect. If you see the message: “This package will run a program to determine if the software can be installed” , Click on “Continue”. The Cisco AnyConnect program will now be visible in Finder>Applications>Cisco. If needed, the supporting files for the package will be located in Macintosh HD>opt>cisco>vpn>profile. Information on advanced instructions for Cisco AnyConnect VPN troubleshooting can be found in the Advanced Instructions for AnyConnect for VPN for Mac OS X. The native OS X Cisco VPN adds these routes automatically and removes them when you disconnect. That's one of the things that differentiates the Cisco VPN client from the standard IPSec client. Let's take a look at what gateway is used when sending traffic to apple.com from within the Terminal application: VPN Tracker is your smart VPN client Mac choice. Use the VPN Tracker Mac App, the leading IPSec Mac VPN client, for secure VPN data connections on Apple macOS Catalina (10.15), macOS Mojave (10.14), macOS High Sierra (10.13), macOS Sierra (10.12), Mac OS X El Capitan (Mac OS X 10.11). The VPN Tracker program is a VPN client software for Mac