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    Help setup nested (multi-hop) Surfshark VPN chain inside pfSense

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    • S Offline
      subhan2k
      last edited by

      Help setup nested (multi-hop) Surfshark VPN chain inside pfSense
      ~ my configurations my for VPN 1: https://pastebin.com/mUNEbJAV — I’m a complete newbie using pfsense first time.

      I’m running pfSense inside VMware.

      I’ve added two network adapters in VMware:

      • One adapter is set to Bridged (for WAN / internet connection)

      • The second adapter is set to a LAN Segment, and this LAN segment is connected to my Windows VMware


      💡 Additional Questions

      • For VPN2 setup, should I use the same configuration as above (VPN 1) for the multi-hop (nested) setup?I’m asking because I don’t know if VPN2 needs any changes or if both should be exactly the same.

      • After I add VPN2, how do I make the multi-hop setup work (VPN1 → VPN2)?

      And how can I check that it’s working correctly, with no leaks and the network fully isolated from WAN?

      My goal is "if either VPN1 or VPN2 goes down, there should be no connection at all (no DNS, NTP, or internet fallback through WAN). Basically, zero leaks and no failover to my local ISP."

      pfSense → [Surfshark VPN1 → Surfshark VPN2] → Internet


      • Right now, my default gateway is WAN_DHCP. For the multi-hop setup, do I need to change the default gateway to VPN 1?

      If yes, when I change the default gateway to VPN1, the VPN goes offline and the internet stops working.

      • Do I need to add static routes for nested multi-hop setup?

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