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Site-to-Site VPN Troubleshooting: Works Up, not Down

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I set up a S2S VPN connecting my Azure Subscription to my local network using 2012 R2 RRAS.

VPN connects, stays up, shows some small amount of bandwidth successfully traversing sites. I can ping/RDP/browse from on-prem up to Azure via private IP ranges fine, but I cannot talk from my Azure VMs to any local, on-prem resources. Firewalls are off on both sides. Ping up resolves and responds but pinging down returns 'timed out', not 'destination unavailable'

In digging in, the one anomaly I find is that the Demand Dial PPP connection created in RRAS has an AutoConfiguration IP address (169.254.x.x) rather than one from my on-prem IP range which I would have expected.

Anyone worked through this before? Thank you!


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