I'm having the same issue - and it DOES seem like it matters if they're hosted on Windows. I can both ping and access SMB shares hosted on Linux servers behind the VPN, but can neither ping nor access shares hosted by Windows machines on the LAN (I can access them when I'm directly on the LAN - not via VPN).

INTELLIGENT BUSINESS ROUTER: It features dual-WAN ports for load balancing or fail-over modes, and encrypted Virtual Private Network (VPN) access for remote users. Dual-WAN ports smooth network loading, minimize network downtime, and allow employees to access your network from the Internet—all with a single router. File and Printer Sharing (SMB-In) (There are additional rules, but I didn't care about printer sharing. The same changes would apply if you want those.) File and Printer Sharing appears to default to "Local subnet" only. You'll need to add the subnet of your VPN clients. Modify each of those rules as follows: Open the Properties dialog for the rule. To access volumes and files hosted on a file server, one of several available distributed file system protocols must be used. As of 2018, the most common protocols are SMB/CIFS (default for Windows and macOS 10.9 or newer), AFP (default for macOS prior to 10.9), NFS (default for Linux and most UNIX operating system), WebDAV (based on HTTP, vendor neutral). All SMB authentication still happens normally within the TLS tunnel (as if it was a VPN) so SMB is not relying on cert-based identity or auth - it will still use NTLM or Kerberos (with KDC proxy). This model is just swapping out the transport, SMB is unchanged. SMB-SSL VPN: How to block access to the SRA device from specific source IP address or range using G. 03/26/2020 1105 9558. DESCRIPTION: SMB-SSL VPN: How to block access to the SRA device from specific source IP address or range using Geo-IP/Botnet filter. In some cases we would like to set up a blacklist or whitelist to limit the Internet access. For example, sometimes we don’t want the LAN users to use IPsec VPN, and we may want to provide http website access only. In this article, we would guide you how to set up these scenarios by setting up Access Rules.

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As I understand it, with signed SMB enabled you wouldn't be able to connect Mac->Windows server (in Server 2003 enabled by default) using SMB without Thursby's Admit Mac at the office either. I don't think Samba supports signed SMB (yet?). The VPN connection forces MTU down between VPN client and VPN server (tunnel endpoints).

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Troubleshooting Windows/SMB Share Access from OpenVPN Clients¶ If Windows/SMB shares are not able to accessed by OpenVPN clients but other services work as desired, visit VPN > OpenVPN, edit the server in question, and check Enable NetBIOS over TCP/IP. It may also be necessary to set MSS clamping for VPNs.