I am attempting to set up Azure (Resource Manager) Site-to-Site VPN connection between my Azure Virtual Network and an on-premises Cisco ASA running 8.2. I've read elsewhere that folks have had success setting this up with 8.2 despite it not being on the approved devices list, at it is capable of meeting all the same requirements as 8.3 and above.

I used the directions found at https://docs.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-site-to-site-resource-manager-portal to set up the Azure side of things. Then I set up the ASA using the IPSec VPN wizard. I do have a dedicated IP address for my on-premises site and the ASA uses it as the outside interface.

When I check back on the connection blade on Azure, it shows it is cycling between connecting and succeeded. No data is transferred and I'm unable to ping my domain controller on the Azure Virtual Network from any of the PCs that are connected on my on-premises inside interface. NAT rules were automatically created between the on-premises network and the Azure virtual network when I ran the IPsec VPN Wizard on the ASA.

Not sure what else I can do at this point. I'm ready to pull my hair out, though. Here is a quick gist of my settings.

Azure Peer IP: 52.183.x.x Azure Vnet Address Space: On-Premises IP: 50.388.x.x On-Premises Address Space:

Any thoughts/help would be greatly appreciated.

EDIT: I should add we are in the middle of migrating from on-prem to the cloud. All PCs on the inside network I've been referring to are currently connected to another domain controller. I'd like to set up the Site-to-Site VPN and start pulling the PCs off the on-prem domain and adding them to our Azure domain.


Unfortunately, that device (cisco ASA 8.2) is not on the list of known compatible devices, the minimum OS version is 8.3, you should upgrade to version 8.3 at least. enter image description here The main issue in version 8.2 is that it doesn’t understand that there is an IKE version 2, so the commands with ikev1 are wrong to it. Cisco ASA version 8.2 does not support Azure site-to-site VPN, because ikev1 isn’t understood by IOS 8.2.

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.