Phone with VPN

ASA Anyconnect VPN

CCNP Security Nov 23, 2025

Benefits and features of Anyconnect

  • Supports DTLS - Datagram Transport Layer Security
  • Supports all major operating systems
  • Support for start before logon (SBL)
  • Automatic or manual (MSI package) installation
  • Supports IPv6 internal networks
  • Standalone client (doesn’t need a web browser)
  • Certificate-based authentication
  • Dynamic Access Policy (DAP - Failover)
  • Supports Cisco Secure Desktop

SSL VPN Wizard

SSL VPN Wizard
SSL VPN Wizard
SSL VPN Interface
SSL VPN Interface
SSL VPN User Authentication
SSL VPN User Authentication
SSL VPN Group Policy
SSL VPN Group Policy
SSL VPN IP Address Pools and Client Image
SSL VPN IP Address Pools and Client Image

The wizard only allows one image to be selected, images for other platfoms can be added later.

NAT Exemption Warning
NAT Exemption Warning
access-list NONAT ext permit 172.30.10.0 255.255.255.0 172.30.10.0 255.255.255.0
nat (inside) 0 access-list NONAT
SSL VPN Client Portal
SSL VPN Client Portal

Split Tunnel Configuration

VPN Group Policy
VPN Group Policy

To enable split tunneling, the networks need to be added to the Network List and the Policy needs to be changed.

Network List
Network List
VPN Group Policy with Split Tunneling
VPN Group Policy with Split Tunneling

Client Settings

Turn off Keep Installer on Client system to remove client from the users device on disconnect

DTLS is enabled by default

SSL VPN Client Settings
SSL VPN Client Settings

Download the client automatically once the user signs into the portal.

Login Settings
Login Settings
Dead Peer Detection
Dead Peer Detection

Troubleshooting Commands

show vpn-sessiondb detail
show vpn-sessiondb detail
show vpn-sessiondb detail
show crypto protocol statistics ssl
show crypto protocol statistics ssl
show crypto protocol statistics ssl
debug webvpn

debug AAA

Certificate based authentication

Enable local Certificate Authority server

CA Server
CA Server

Create a self-signed certificate

new identity certificate
new identity certificate

Add users to the database a generate a one time password for the users to get the certificate on their device

User Database
User Database
View OTP
View OTP

Enable Anyconnect

Anyconnect
Anyconnect

SSL VPN Connection Profile

SSL VPN Connection Profile
SSL VPN Connection Profile

Group Policy

Group Policy
Group Policy

Client login using certificate

client certificate login
client certificate login

login will fail as the client does not currently have a certificate, can use the link to request a certificate using the OTP.

Certificate Validation Failure
Certificate Validation Failure
ASA Local Certificate Authority
ASA Local Certificate Authority
Certificate Download
Certificate Download

Use the OTP as the password for the private key when importing the certificate.

Certificate Import Wizard
Certificate Import Wizard

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