Unable to connect to OpenVPN server hosted by office pfSense VM



  • 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.



  • You dont get an IP from DHCP



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


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