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    Unable to connect to OpenVPN server hosted by office pfSense VM

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    • J
      johnny420 last edited by

      Hi good folks at Netgate Community.

      Let me start off by saying that I'm very new to pfSense and VPNs too in general and hence my questions might sound stupid a bit so please go easy on me. Thanks in advance.

      Now, coming straight to the point, when I try to connect using OpenVPN client export utility to my office pfSense firewall, I get the following logs:
      Fri Apr 10 11:57:37 2020 OpenVPN 2.4.8 x86_64-w64-mingw32 [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [AEAD] built on Oct 31 2019
      Fri Apr 10 11:57:37 2020 Windows version 6.2 (Windows 8 or greater) 64bit
      Fri Apr 10 11:57:37 2020 library versions: OpenSSL 1.1.0l 10 Sep 2019, LZO 2.10
      Fri Apr 10 11:57:39 2020 TCP/UDP: Preserving recently used remote address: [AF_INET]183.82.0.182:1210
      Fri Apr 10 11:57:39 2020 UDP link local (bound): [AF_INET][undef]:0
      Fri Apr 10 11:57:39 2020 UDP link remote: [AF_INET]183.82.0.182:1210
      Fri Apr 10 11:57:39 2020 WARNING: this configuration may cache passwords in memory -- use the auth-nocache option to prevent this
      Fri Apr 10 11:57:40 2020 [CA 2] Peer Connection Initiated with [AF_INET]183.82.0.182:1210
      Fri Apr 10 11:57:46 2020 open_tun
      Fri Apr 10 11:57:46 2020 TAP-WIN32 device [Local Area Connection] opened: \.\Global{087EE999-89D8-4104-AA1B-E271644DFC1A}.tap
      Fri Apr 10 11:57:46 2020 Set TAP-Windows TUN subnet mode network/local/netmask = 10.0.13.0/10.0.13.18/255.255.255.0 [SUCCEEDED]
      Fri Apr 10 11:57:46 2020 Notified TAP-Windows driver to set a DHCP IP/netmask of 10.0.13.18/255.255.255.0 on interface {087EE999-89D8-4104-AA1B-E271644DFC1A} [DHCP-serv: 10.0.13.254, lease-time: 31536000]
      Fri Apr 10 11:57:46 2020 Successful ARP Flush on interface [4] {087EE999-89D8-4104-AA1B-E271644DFC1A}
      Fri Apr 10 11:58:21 2020 Warning: route gateway is not reachable on any active network adapters: 192.168.1.10
      Fri Apr 10 11:58:21 2020 SYSTEM ROUTING TABLE
      Fri Apr 10 11:58:21 2020 0.0.0.0 0.0.0.0 10.0.0.1 p=0 i=20 t=4 pr=3 a=2889 h=0 m=35/0/0/0/0
      Fri Apr 10 11:58:21 2020 0.0.0.0 128.0.0.0 10.0.13.1 p=0 i=4 t=4 pr=3 a=0 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 10.0.0.0 255.255.255.0 10.0.0.7 p=0 i=20 t=3 pr=2 a=2889 h=0 m=291/0/0/0/0
      Fri Apr 10 11:58:21 2020 10.0.0.7 255.255.255.255 10.0.0.7 p=0 i=20 t=3 pr=2 a=2889 h=0 m=291/0/0/0/0
      Fri Apr 10 11:58:21 2020 10.0.0.255 255.255.255.255 10.0.0.7 p=0 i=20 t=3 pr=2 a=2889 h=0 m=291/0/0/0/0
      Fri Apr 10 11:58:21 2020 10.0.13.0 255.255.255.0 10.0.13.18 p=0 i=4 t=3 pr=2 a=35 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 10.0.13.18 255.255.255.255 10.0.13.18 p=0 i=4 t=3 pr=2 a=35 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 10.0.13.255 255.255.255.255 10.0.13.18 p=0 i=4 t=3 pr=2 a=35 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 127.0.0.0 255.0.0.0 127.0.0.1 p=0 i=1 t=3 pr=2 a=2919 h=0 m=331/0/0/0/0
      Fri Apr 10 11:58:21 2020 127.0.0.1 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=2919 h=0 m=331/0/0/0/0
      Fri Apr 10 11:58:21 2020 127.255.255.255 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=2919 h=0 m=331/0/0/0/0
      Fri Apr 10 11:58:21 2020 128.0.0.0 128.0.0.0 10.0.13.1 p=0 i=4 t=4 pr=3 a=0 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 183.82.0.182 255.255.255.255 10.0.0.1 p=0 i=20 t=4 pr=3 a=0 h=0 m=291/0/0/0/0
      Fri Apr 10 11:58:21 2020 192.168.56.0 255.255.255.0 192.168.56.1 p=0 i=23 t=3 pr=2 a=2903 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 192.168.56.1 255.255.255.255 192.168.56.1 p=0 i=23 t=3 pr=2 a=2903 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 192.168.56.255 255.255.255.255 192.168.56.1 p=0 i=23 t=3 pr=2 a=2903 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 192.168.137.0 255.255.255.0 192.168.137.1 p=0 i=9 t=3 pr=2 a=2862 h=0 m=311/0/0/0/0
      Fri Apr 10 11:58:21 2020 192.168.137.1 255.255.255.255 192.168.137.1 p=0 i=9 t=3 pr=2 a=2862 h=0 m=311/0/0/0/0
      Fri Apr 10 11:58:21 2020 192.168.137.255 255.255.255.255 192.168.137.1 p=0 i=9 t=3 pr=2 a=2862 h=0 m=311/0/0/0/0
      Fri Apr 10 11:58:21 2020 224.0.0.0 240.0.0.0 127.0.0.1 p=0 i=1 t=3 pr=2 a=2919 h=0 m=331/0/0/0/0
      Fri Apr 10 11:58:21 2020 224.0.0.0 240.0.0.0 192.168.56.1 p=0 i=23 t=3 pr=2 a=2907 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 224.0.0.0 240.0.0.0 10.0.13.18 p=0 i=4 t=3 pr=2 a=2906 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 224.0.0.0 240.0.0.0 10.0.0.7 p=0 i=20 t=3 pr=2 a=2899 h=0 m=291/0/0/0/0
      Fri Apr 10 11:58:21 2020 224.0.0.0 240.0.0.0 192.168.137.1 p=0 i=9 t=3 pr=2 a=2864 h=0 m=311/0/0/0/0
      Fri Apr 10 11:58:21 2020 255.255.255.255 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=2919 h=0 m=331/0/0/0/0
      Fri Apr 10 11:58:21 2020 255.255.255.255 255.255.255.255 192.168.56.1 p=0 i=23 t=3 pr=2 a=2907 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 255.255.255.255 255.255.255.255 10.0.13.18 p=0 i=4 t=3 pr=2 a=2906 h=0 m=281/0/0/0/0
      Fri Apr 10 11:58:21 2020 255.255.255.255 255.255.255.255 10.0.0.7 p=0 i=20 t=3 pr=2 a=2899 h=0 m=291/0/0/0/0
      Fri Apr 10 11:58:21 2020 255.255.255.255 255.255.255.255 192.168.137.1 p=0 i=9 t=3 pr=2 a=2864 h=0 m=311/0/0/0/0
      Fri Apr 10 11:58:21 2020 SYSTEM ADAPTER LIST
      Fri Apr 10 11:58:21 2020 Realtek PCIe FE Family Controller
      Fri Apr 10 11:58:21 2020 Index = 22
      Fri Apr 10 11:58:21 2020 GUID = {EFAB4C93-60E5-4CF0-9357-C84608D1488A}
      Fri Apr 10 11:58:21 2020 IP = 0.0.0.0/0.0.0.0
      Fri Apr 10 11:58:21 2020 MAC = 74:86:7a:3e:ce:ab
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP SERV =
      Fri Apr 10 11:58:21 2020 DHCP LEASE OBTAINED = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DHCP LEASE EXPIRES = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 Bluetooth Device (Personal Area Network)
      Fri Apr 10 11:58:21 2020 Index = 11
      Fri Apr 10 11:58:21 2020 GUID = {6B82F3AB-BC56-4D39-88CC-CCAB7AE453BF}
      Fri Apr 10 11:58:21 2020 IP = 0.0.0.0/0.0.0.0
      Fri Apr 10 11:58:21 2020 MAC = e4:70:b8:ec:dc:5d
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP SERV =
      Fri Apr 10 11:58:21 2020 DHCP LEASE OBTAINED = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DHCP LEASE EXPIRES = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 Kaspersky Security Data Escort Adapter
      Fri Apr 10 11:58:21 2020 Index = 13
      Fri Apr 10 11:58:21 2020 GUID = {7DD0FB9F-9A90-49F2-80B6-F5F66FF431D5}
      Fri Apr 10 11:58:21 2020 IP = 0.0.0.0/0.0.0.0
      Fri Apr 10 11:58:21 2020 MAC = 00:ff:7d:d0:fb:9f
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 VirtualBox Host-Only Ethernet Adapter
      Fri Apr 10 11:58:21 2020 Index = 23
      Fri Apr 10 11:58:21 2020 GUID = {FD4E6E81-B6CC-448F-A4FB-BF0D11C27B0A}
      Fri Apr 10 11:58:21 2020 IP = 192.168.56.1/255.255.255.0
      Fri Apr 10 11:58:21 2020 MAC = 0a:00:27:00:00:17
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 Kaspersky Security Data Escort Adapter #2
      Fri Apr 10 11:58:21 2020 Index = 19
      Fri Apr 10 11:58:21 2020 GUID = {DD24CE3D-CFAB-4FE1-8C0C-5743529C5E23}
      Fri Apr 10 11:58:21 2020 IP = 0.0.0.0/0.0.0.0
      Fri Apr 10 11:58:21 2020 MAC = 00:ff:dd:24:ce:3d
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP SERV =
      Fri Apr 10 11:58:21 2020 DHCP LEASE OBTAINED = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DHCP LEASE EXPIRES = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 TAP-Windows Adapter V9
      Fri Apr 10 11:58:21 2020 Index = 4
      Fri Apr 10 11:58:21 2020 GUID = {087EE999-89D8-4104-AA1B-E271644DFC1A}
      Fri Apr 10 11:58:21 2020 IP = 10.0.13.18/255.255.255.0
      Fri Apr 10 11:58:21 2020 MAC = 00:ff:08:7e:e9:99
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP SERV = 10.0.13.254/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP LEASE OBTAINED = Fri Apr 10 11:57:46 2020
      Fri Apr 10 11:58:21 2020 DHCP LEASE EXPIRES = Sat Apr 10 11:57:46 2021
      Fri Apr 10 11:58:21 2020 DNS SERV = 192.168.1.10/255.255.255.255 8.8.4.4/255.255.255.255
      Fri Apr 10 11:58:21 2020 Intel(R) Dual Band Wireless-AC 7260
      Fri Apr 10 11:58:21 2020 Index = 20
      Fri Apr 10 11:58:21 2020 GUID = {E7EDFFF3-FD63-4695-A14F-B63D23655D2F}
      Fri Apr 10 11:58:21 2020 IP = 10.0.0.7/255.255.255.0
      Fri Apr 10 11:58:21 2020 MAC = e4:70:b8:ec:dc:59
      Fri Apr 10 11:58:21 2020 GATEWAY = 10.0.0.1/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP SERV = 10.0.0.1/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP LEASE OBTAINED = Fri Apr 10 11:10:12 2020
      Fri Apr 10 11:58:21 2020 DHCP LEASE EXPIRES = Sat Apr 11 11:10:12 2020
      Fri Apr 10 11:58:21 2020 DNS SERV = 10.0.0.1/255.255.255.255
      Fri Apr 10 11:58:21 2020 Microsoft Wi-Fi Direct Virtual Adapter
      Fri Apr 10 11:58:21 2020 Index = 10
      Fri Apr 10 11:58:21 2020 GUID = {60948B82-1BB5-4174-A0BA-C4F5EF833177}
      Fri Apr 10 11:58:21 2020 IP = 0.0.0.0/0.0.0.0
      Fri Apr 10 11:58:21 2020 MAC = e4:70:b8:ec:dc:5a
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DHCP SERV =
      Fri Apr 10 11:58:21 2020 DHCP LEASE OBTAINED = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DHCP LEASE EXPIRES = Fri Apr 10 11:58:21 2020
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 Microsoft Wi-Fi Direct Virtual Adapter #2
      Fri Apr 10 11:58:21 2020 Index = 9
      Fri Apr 10 11:58:21 2020 GUID = {5A1C8256-57B6-4083-BF1E-0A97D9AA9064}
      Fri Apr 10 11:58:21 2020 IP = 192.168.137.1/255.255.255.0
      Fri Apr 10 11:58:21 2020 MAC = e6:70:b8:ec:dc:59
      Fri Apr 10 11:58:21 2020 GATEWAY = 0.0.0.0/255.255.255.255
      Fri Apr 10 11:58:21 2020 DNS SERV =
      Fri Apr 10 11:58:21 2020 Initialization Sequence Completed With Errors ( see http://openvpn.net/faq.html#dhcpclientserv )

      And the dialog stays open and doesn't close. But the thing is that I'm able to ping the local servers in the office. But I can't keep scratching my head and thinking if something is still wrong. Would you guys be able to help me with this? What is happening does not seem to be a perfect execution.

      1 Reply Last reply Reply Quote 0
      • C
        Cool_Corona last edited by

        You dont get an IP from DHCP

        1 Reply Last reply Reply Quote 0
        • J
          johnny420 last edited by

          Thank you for your reply, however, could you also help in how to rectify that? Should I post any other logs?

          1 Reply Last reply Reply Quote 0
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