Give any user highly secure access to the enterprise network, from any device, at any time, in any location.

Cisco AnyConnect is the recommended VPN client for Mac. The built-in VPN client for Mac is another option but is more likely to suffer from disconnects. What I found that seems to have resolved the issue is by turning ON 'Connect On Demand' within the Cisco AnyConnect App on my iPhone and iPad and making sure my organization's domain was listed. This is found in Cisco AnyConnect version 4.9.005 by modifying the VPN connection (tapping the little (i) next to the connection), then tapping.

Cisco AnyConnect - Empower your employees to work from anywhere, on company laptops or personal mobile devices, at any time. AnyConnect simplifies secure endpoint access and provides the security necessary to help keep your organization safe and protected.

If the ASA assigns the AnyConnect connection only an IPv4 address or only an IPv6 address, you can now configure the Client Bypass Protocol to drop network traffic for which the ASA did not assign an IP address, or allow that traffic to bypass the ASA and be sent from the client unencrypted or “in the clear”. Cisco AnyConnect 4.8.00175 is the first version that officially supports operation on macOS Catalina and contains no 32-bit code. Which implies there’s a bug or mis-configuration here. If there’s no newer AnyConnect version and no other support notes, contact Cisco Support. Find the newly installed AnyConnect application. To open it, tap on the AnyConnect icon. The first time you start AnyConnect, you’ll get this message: “ Cisco AnyConnect Secure Mobility Client extends the VPN capabilities of your device.

Gain more insight into user and endpoint behavior with full visibility across the extended enterprise. With AnyConnect's Network Visibility Module (NVM), you can defend more effectively and improve network operations.

Defend against threats, no matter where they are. For example, with Cisco Identity Services Engine (ISE), you can prevent noncompliant devices from accessing the network. And with Cisco Umbrella Roaming, you can extend protection when users are off the VPN.

Provide a consistent user experience across devices, both on and off premises, without creating a headache for your IT teams. Simplify management with a single agent.

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