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I'm going to reference this question where I was asking about VPNs and Azure.

https://security.stackexchange.com/questions/146041/migrating-iis-to-azure

However, this brings me to my next question. If my azure file share reside at myfileshare.core.windows.net (a host completely off my Azure VNET, and controlled by microsoft) how can I route traffic through my VPN to the Azure VNET to ultimately connect to myfileshare.core.windows.net?

I'm aware that on my network I can perform forced tunneling, but (in the most general sense) how would I go about this?

Once I'm routing all the needed traffic over my VPN gateway to Azure, how does it know where to send my packets?

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Based on your description, it seems that you want to mount Azure File Shares on your on-pre PC, but ISP blocks port 445.

Based on my knowledge, Site-to-Site VPN could not achieve your scenario. When the S2S VPN is established, VMs on the VNET communicate with the on-premises computers through their private IP addresses. But the File share is a public IP address, the traffic will continue to direct your IIS.

You could setup Windows Azure (Server 2012) as an SSTP and L2TP VPN Provider, your client PC connects to this VPN. I test it in my lab, it works for me. I could mount file share even though ISP block 445 Port. More information about how to setup Azure Windows as a VPN provider, please refer to the article.

Also, you could refer to this article which is the same with you.

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