Cisco IPsec VPN setup for Apple devices

Use this section to configure your Cisco VPN server for use with iOS, iPadOS, and macOS, all of which support the Cisco network firewalls Adaptive Security Appliance 5500 Series and Private Internet Exchange. They also support Cisco IOS VPN routers with IOS version 12.4(15)T or later. VPN 3000 Series Concentrators don’t support VPN capabilities.

Authentication methods

iOS, iPadOS, and macOS support the following authentication methods:

Preshared key IPsec authentication with user authentication using the xauth command.
Client and server certificates for IPsec authentication, with optional user authentication using xauth.
Hybrid authentication, where the server provides a certificate and the client provides a preshared key for IPsec authentication. User authentication is required and provided using xauth, which includes the authentication method’s user name with password, and RSA SecurID.

Authentication groups

The Cisco Unity protocol uses authentication groups to group users based on a common set of parameters. You should create an authentication group for users. For preshared key and hybrid authentication, the group name needs to be configured on the device with the group’s shared secret (preshared key) as the group password.

When using certificate authentication, there’s no shared secret. A user’s group is determined from fields in the certificate. The Cisco server settings can be used to map fields in a certificate to user groups.

RSA-Sig needs to be the highest priority on the ISAKMP (Internet Security Association and Key Management Protocol) priority list.

IPsec settings and descriptions

You can specify these settings to define how IPsec is implemented:

Mode: Tunnel mode.
IKE exchange modes: Aggressive mode for preshared key and hybrid authentication, or Main mode for certificate authentication.
Encryption algorithms: 3DES, AES-128, or AES256.
Authentication algorithms: HMAC-MD5 or HMAC-SHA1.
Diffie-Hellman Groups: Group 2 is required for preshared key and hybrid authentication, group 2 with 3DES and AES-128 for certificate authentication, and group 2 or 5 with AES-256.
Perfect Forward Secrecy (PFS): For IKE phase 2, if PFS is used, the Diffie-Hellman Group needs to be the same as was used for IKE phase 1.
Mode configuration: Needs to be enabled.
Dead peer detection: Recommended.
Standard NAT traversal: Supported and can be enabled (IPsec over TCP isn’t supported).
Load balancing: Supported and can be enabled.
Rekeying of phase 1: Not currently supported. It’s recommend that rekeying times on the server be set to one hour.
ASA address mask: Make sure all device address pool masks are either not set, or set to 255.255.255.255. For example:
asa(config-webvpn)# ip local pool vpn_users 10.0.0.1-10.0.0.254 mask 255.255.255.255.
If you use the recommended address mask, some routes assumed by the VPN configuration might be ignored. To avoid this, make sure your routing table contains all necessary routes, and make sure the subnet addresses are accessible before deployment.
- Application version: The client software version is sent to the server, letting the server accept or reject connections based on the device’s software version.
- Banner: The banner (if configured on the server) is displayed on the device, and the user needs to accept it or disconnect.
- Split tunnel: Supported.
- Split DNS: Supported.
- Default domain: Supported.

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Apple Platform Deployment

Cisco IPsec VPN setup for Apple devices

Authentication methods

Authentication groups

IPsec settings and descriptions