VPN Is no longer working to PPTP VPNs to Dreytek Routers via Windows Built in VPN

So we rebuilt the network recently, the only thing that had changed is the LAN range which doesn’t share the same LAN range as any of the LANs we are trying to connect to over the Windows Built-in VPN > Dreytek

Works fine on other pfsenses out in the world and on home networks

The error comes back as authentication fails, it’s almost like it hits the router and connects then drops creds, ive wiped creds and tried again, and again this works fine on other networks the creds are fine.

Tried changing NAT to Auto on pfsense

Tried looking for blocks in the logs in pfsense

Tried Any > Any rules on WAN + LAN and still doesn’t connect

Tried dreytek smart VPN software instead of windows built in

Our lan network is 10.10.20.***

the Dreytek routers are on 192.168.44.***

Apart from factory resetting the pfsense and trying to see if that fixes it what else can i do?

dont forget protocol 47

PPTP no longer working? Good!

Where was the authentication server before? Maybe you forgot to add a NAT rule in your config to point to it.

Also, in my years of MSP experience Windows VPN is notorious for no longer working after a Windows Update. Encryption standards and allowed protocols change a lot. I do not recommend this for a long-term VPN so I’d consider an alternative at this point. OpenVPN is free and can be setup on the firewall. SoftEther is also free and can be installed on a Windows Server or on the pfSense itself (much harder to do).

Bottom line is you need to get away from the Windows VPN and move towards something with a dedicated app. Trust me on this and the others that will hopefully back me up.

But it’s so secure :wink:

Also, I’ve never heard of DrayTek before. I did some research on their boxes and it just claims what they can do. I assume it is pfSense installed on those??

Rock solid! But as the other poster said GRE / Protocol 47