using SMB over VPN to a azure VM with windows 2012 R2

Reshef Katz | CyberGymIEC 0 Reputation points
2024-01-17T12:32:15.3833333+00:00

Hello, after recently migrating my server environment to azure, which consists of windows server 2012 R2 servers mostly, I am having difficulties using SMB, the developers used the \<server-IP-address\c$ share in the past. I believe I know the cause of the issue, and am looking to hear if there is anyway around it.... since I am able to make the connection with a windows server 2022 without issues, and also connecting between the servers in azure is fine, my only conclusion is that it has an issue with the VPN connection, seeing that both the azure VPN client, and my site2site connection (between a checkpoint and vpn gateway) fail to make the connection it leads me to think that server 2012 R2 does not support SMB 3.0 over encrypted data and that the 3.1.1 that the server 2022 supports does. things I have tried include, disabling the windows firewall, changing GPO policies according to different guides I have found, and copying all the different SMB server configurations between the servers. on another note, I have used tcpdump on the different connections to spot the what might be going wrong, and I had noticed that the connection that fails, gets [S] and [S.] and [R.] flags, while the successful one doesn't. open for thoughts and ideas, and prayers

Azure VPN Gateway
Azure VPN Gateway
An Azure service that enables the connection of on-premises networks to Azure through site-to-site virtual private networks.
1,528 questions
Windows Server 2012
Windows Server 2012
A Microsoft server operating system that supports enterprise-level management, data storage, applications, and communications.
1,588 questions
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