[REQUEST] macOS Catalina Can't Connect to SMB Over VPN

[Slaters Kustum Machines]

I have a user that has been using a MacBook Pro with Tunnelblick to connect to Sophos XG 210 with SSL VPN. SMB shares were working fine and all of a sudden they do not work.

I can ping the server by IP and DNS name, but cannot connect to the shares by IP or name. The user doesn't believe there were any macOS updates recently and Tunnelblick is full up to date.

I haven't seen anything about server updates causing SMB issues. Server is server 2019.

 

[Markverhyden]

Are you sending all the traffic though the tunnel? Used to be that was not necessary. But the last year or so I've had problems and sending all traffic through the tunnel seemed to solve the problem.

 

[Slaters Kustum Machines]

Are you sending all the traffic though the tunnel? Used to be that was not necessary. But the last year or so I've had problems and sending all traffic through the tunnel seemed to solve the problem.

No, we're doing split DNS, but I can certainly give that a shot.

 

[Slaters Kustum Machines]

Made the change, but won't know if it works for a couple weeks. I'll try to remember to report back.

 

[Markverhyden]

As I mentioned I had problems, basically same thing you had, was working then not. At some point it suddenly stopped working on all sites, including myself. Found that sending everything over the tunnel worked. But that puts an added load on the remote site.

 

[PaddyT]

I have a user that has been using a MacBook Pro with Tunnelblick to connect to Sophos XG 210 with SSL VPN. SMB shares were working fine and all of a sudden they do not work.

I can ping the server by IP and DNS name, but cannot connect to the shares by IP or name. The user doesn't believe there were any macOS updates recently and Tunnelblick is full up to date.

I haven't seen anything about server updates causing SMB issues. Server is server 2019.

I would suggest asking about it here. I've had some incidents where users had issues with VPN's, there were super helpful. They did what I should be doing quite a few times )

 

[mark-tech]

Notice this was not solved so here's my input...I had this issue once before and used the article below to resolve it. Hope this helps. Basically, I had to ensure that the remote office network was not using the default IP addressing most routers put out for home use so I changed it and it worked.

MacOS can't connect to SMB shares over VPN

Hello, As we all know, MS has nerfed L2TP VPN connections recently, which has been fun… Ever since the recent updates (KB5009624 / KB5009557) and their OOB fixes (KB5010794 / KB5010791) for Server 2012r2 / 2019, my MacOS (Monterey 12.1) remote workers have been unable to access our SMB shares...

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