Unable to connect to remote server using SMB over VPN


I'm Unable to connect to the Remote server via SMB over the VPN from a Mac. Able to ping the device, and have tried connecting using the host-name and the internal IP address.
No blocked traffic showing on the firewall

Technical InformationAsked:
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What happens when you try to telnet to the server on port 445? If you can connect then the network is working properly. If you can't then you have a network or firewall problem.
Mark BullockQA EngineerCommented:
The command would be: telnet yourserver.yourdomain.com 445

If you don't have telnet installed, here are the instructions.
Technical InformationAuthor Commented:
amateur question but would I have to be in the VPN or can I do it from where I am? I'm not in the same building
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You need from the Mac over the VPN.
Technical InformationAuthor Commented:
I am able to connect to the share from a spare Mac on the users network. It seems to be an issue local to this Mac. I have also just updated to Yosemite and still no luck
Jeff GloverSr. Systems AdministratorCommented:
If you can connect from a MAC on the local network then it is probably something to do with your VPN. Can you ping the internal address of the file share server from your MAC when it is connected via VPN?
Technical InformationAuthor Commented:
The issue seemed to be the users home network being on the same IP address range as the DC at his office.

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I believe that you are always going to have unreliable operation if the remote network overlaps with the local subnet. You should change the addressing one one of the subnets.
Technical InformationAuthor Commented:
After further testing with wireshark packet capture, there was no difference in the traffic between when share access works and when it doesn't.

After further testing it seems the issue is being caused by users local network being on the same IP address range as the DC server IP address range.

After disconnecting and re-connecintg the VPN a few time connection to the SMB share seems to work again
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