Azure Site to Site VPN to a Cisco ASA v8.6+

Published On: 2021-03-22By:

Recently I was moving a client from their existing CoLo to Azure. Right now they are going with IaaS for their web servers and PaaS (Azure SQL Managed Instance) for their databases. This means that we needed to set up a Site-to-Site VPN between their existing on-prem environment at the CoLo and their Azure vNet so that they could transfer everything over, replicate AD, etc. Their on-prem router was a Cisco ASA running version 8.6 of the Cisco IOS.

Our plan was to enable BGP on the connection as we had several vNet’s that we wanted to have connected to the VPN, and we only wanted one VPN gateway. However, with a Cisco ASA, we found that BGP wasn’t an option as Azure has a new feature available within the configuration of the connect called “Policy Based Traffic Selector” which required that BGP be disabled.

Site-To-Site VPN Connection Properties in the Azure Portal

The problem that we were facing with our VPN connection was that even though all of the IKE Phase 1 and IKE Phase 2 settings were connect (we verified them against the Cisco ASA settings probably 10 times) we were still getting protocol mismatch when the VPN connection would attempt to come online.

We eventually tried turning on the “Use policy based traffic selector” option on the connection (which made us disable BGP) and the connection came up on the first try. For this, we were using a policy-based VPN Endpoint, and these settings are pretty new (it’s March 2021) as I don’t remember seeing them on previous VPN connections.

As you can see from the screenshot above, we specified the IKE Phase 1 and IKE Phase 2 settings, but this doesn’t need to be done as using any of the settings that Microsoft has will work, but we wanted to take the guesswork out of the migration process.

The end result was one of success, the tunnel came up and we could set up things like AD Replication so that we could continue with the migration process.


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