Azure S2S VPN to Cisco Router

Synopsis: Creating Azure S2S VPN to Cisco Router, with a focus on the Cisco Configuration

Published September 3rd, 2025
Last Modified: September 3rd, 2025

Intro: Process recorded during S2S VPN setup between Cisco Router and an Azure Network. This article focuses on the Cisco side of the configuration and assumes a readers knowledge of Azure VPN Deployments.






Quick Run Down

    1.) Create Azure Resources

    2.) Configure Cisco Router

    3.) Trouble Shooting Tips

Create Azure Resources.

  • Azure VNet Gateway

  • Azure Local Gateway:Router Name

  • VNET Connection: Azure2Corp

Configure Cisco Router

    IPSec Profiles

    Modified the existing IPSec Profile for "Microsoft_Azure".
    -Adjusted the IKE version from IKEv1 to IKEv2

    VPN Wizard

    Started VPN Setup Wizard from the 'Getting Started' Panel.
    -Added Connection Name: Corp2Azure
    -Remote Connection: IP Address from Azure VNETGateway
    -Local and Remote Networks:
    -Local IP : 192.168.0.0
    -Subnet Mask: 255.255.0.0
    -Remote IP : Subnet
    -IP Address : 10.0.0.0
    -Subnet Mask: 255.0.0.0
    -Profile: "Microsoft_Azure"
    -Local Pre-Shared Key: PSK created for Azure Local Gateway
    -Remote Pre-Shared Key: Same PSK as above

    Manual Adjustments

    Edit the Connection
    -Under Advanced Settings, enabled 'Keep-Alive'

    TroubleShooting Tips

    VPN is up, but no network connectivity between on-prem and Azure resources & Azure Resources can ping Router appliance.

    - Reset VPN Gateway within Azure > Help

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