The weird thing is that I think I should be able to ping 10.8.0.2 (the server TAP adapter DHCP server) even before establishing connection. I can see in the route table that this address is my gateway to 10.8.0.0/24 so I think this is the reason why everything fails.
You should be able to ping this address right?
I am including the configs, connection log, and the route command input with comments redacted, below.
server config
port 1194
proto udp
dev tun
ca ca.crt
cert server.crt
key server.key
dh dh1024.pem
server 10.8.0.0 255.255.255.0
ifconfig-pool-persist ipp.txt
keepalive 10 120
comp-lzo
persist-key
persist-tun
client config
client
dev tun
proto udp
remote 92.247.58.12 1194
resolv-retry infinite
nobind
persist-key
persist-tun
ca ca.crt
cert client1.crt
key client1.key
ns-cert-type server
comp-lzo
verb 3
server connection log
C:\Program Files\OpenVPN\sample-config>openvpn "my server.ovpn"
Wed Nov 13 13:32:00 2013 OpenVPN 2.3.2 x86_64-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6] built on Aug 22 2013
Wed Nov 13 13:32:00 2013 Diffie-Hellman initialized with 1024 bit key
Wed Nov 13 13:32:00 2013 Socket Buffers: R=[65536->65536] S=[65536->65536]
Wed Nov 13 13:32:00 2013 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
Wed Nov 13 13:32:00 2013 open_tun, tt->ipv6=0
Wed Nov 13 13:32:00 2013 TAP-WIN32 device [Local Area Connection] opened: \\.\Global\{536B08FD-8E6C-4A3A-98CD-FF82F2D121A7}.tap
Wed Nov 13 13:32:00 2013 TAP-Windows Driver Version 9.9
Wed Nov 13 13:32:00 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 10.8.0.1/255.255.255.252 on interface {536B08FD-8E6C-4A3A-98CD-FF82F2D121A7} [DHCP-serv: 10.8.0.2, lease-time: 31536000]
Wed Nov 13 13:32:00 2013 Sleeping for 10 seconds...
Wed Nov 13 13:32:10 2013 Successful ARP Flush on interface [29] {536B08FD-8E6C-4A3A-98CD-FF82F2D121A7}
Wed Nov 13 13:32:10 2013 C:\WINDOWS\system32\route.exe ADD 10.8.0.0 MASK 255.255.255.0 10.8.0.2
Wed Nov 13 13:32:10 2013 ROUTE: CreateIpForwardEntry succeeded with dwForwardMetric1=30 and dwForwardType=4
Wed Nov 13 13:32:10 2013 Route addition via IPAPI succeeded [adaptive]
Wed Nov 13 13:32:10 2013 UDPv4 link local (bound): [undef]
Wed Nov 13 13:32:10 2013 UDPv4 link remote: [undef]
Wed Nov 13 13:32:10 2013 MULTI: multi_init called, r=256 v=256
Wed Nov 13 13:32:10 2013 IFCONFIG POOL: base=10.8.0.4 size=62, ipv6=0
Wed Nov 13 13:32:10 2013 ifconfig_pool_read(), in='client1,10.8.0.4', TODO: IPv6
Wed Nov 13 13:32:10 2013 succeeded -> ifconfig_pool_set()
Wed Nov 13 13:32:10 2013 IFCONFIG POOL LIST
Wed Nov 13 13:32:10 2013 client1,10.8.0.4
Wed Nov 13 13:32:10 2013 Initialization Sequence Completed
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 TLS: Initial packet from [AF_INET]92.247.61.227:58066, sid=f9a769b1 386f975e
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 VERIFY OK: depth=1, C=BG, ST=Sofia, L=Sofia, O=TrdInc, OU=changeme, CN=server, name=server, emailAddress=
zhivkogp@gmail.com
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 VERIFY OK: depth=0, C=BG, ST=Sofia, L=Sofia, O=TrdInc, OU=changeme, CN=client1, name=client1, emailAddress=
zhivkogp@gmail.com
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 1024 bit RSA
Wed Nov 13 13:33:12 2013 92.247.61.227:58066 [client1] Peer Connection Initiated with [AF_INET]92.247.61.227:58066
Wed Nov 13 13:33:12 2013 client1/92.247.61.227:58066 MULTI_sva: pool returned IPv4=10.8.0.6, IPv6=(Not enabled)
Wed Nov 13 13:33:12 2013 client1/92.247.61.227:58066 MULTI: Learn: 10.8.0.6 -> client1/92.247.61.227:58066
Wed Nov 13 13:33:12 2013 client1/92.247.61.227:58066 MULTI: primary virtual IP for client1/92.247.61.227:58066: 10.8.0.6
Wed Nov 13 13:33:14 2013 client1/92.247.61.227:58066 PUSH: Received control message: 'PUSH_REQUEST'
Wed Nov 13 13:33:14 2013 client1/92.247.61.227:58066 send_push_reply(): safe_cap=940
Wed Nov 13 13:33:14 2013 client1/92.247.61.227:58066 SENT CONTROL [client1]: 'PUSH_REPLY,route 10.8.0.1,topology net30,ping 10,ping-restart 120,ifconfig 10.8.0.6 10.8.0.5' (status=1)
client connection log
C:\Program Files\OpenVPN\sample-config>openvpn "my client.ovpn"
Wed Nov 13 13:33:14 2013 OpenVPN 2.3.2 x86_64-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6] built on Aug 22 2013
Wed Nov 13 13:33:15 2013 Socket Buffers: R=[65536->65536] S=[65536->65536]
Wed Nov 13 13:33:15 2013 UDPv4 link local: [undef]
Wed Nov 13 13:33:15 2013 UDPv4 link remote: [AF_INET]92.247.58.12:1194
Wed Nov 13 13:33:15 2013 TLS: Initial packet from [AF_INET]92.247.58.12:1194, sid=1bb2db14 e94b5312
Wed Nov 13 13:33:15 2013 VERIFY OK: depth=1, C=BG, ST=Sofia, L=Sofia, O=TrdInc, OU=changeme, CN=server, name=server, emailAddress=
zhivkogp@gmail.com
Wed Nov 13 13:33:15 2013 VERIFY OK: nsCertType=SERVER
Wed Nov 13 13:33:15 2013 VERIFY OK: depth=0, C=BG, ST=Sofia, L=Sofia, O=TrdInc, OU=changeme, CN=server, name=server, emailAddress=
zhivkogp@gmail.com
Wed Nov 13 13:33:15 2013 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
Wed Nov 13 13:33:15 2013 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Wed Nov 13 13:33:15 2013 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
Wed Nov 13 13:33:15 2013 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Wed Nov 13 13:33:15 2013 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 1024 bit RSA
Wed Nov 13 13:33:15 2013 [server] Peer Connection Initiated with [AF_INET]92.247.58.12:1194
Wed Nov 13 13:33:17 2013 SENT CONTROL [server]: 'PUSH_REQUEST' (status=1)
Wed Nov 13 13:33:17 2013 PUSH: Received control message: 'PUSH_REPLY,route 10.8.0.1,topology net30,ping 10,ping-restart 120,ifconfig 10.8.0.6 10.8.0.5'
Wed Nov 13 13:33:17 2013 OPTIONS IMPORT: timers and/or timeouts modified
Wed Nov 13 13:33:17 2013 OPTIONS IMPORT: --ifconfig/up options modified
Wed Nov 13 13:33:17 2013 OPTIONS IMPORT: route options modified
Wed Nov 13 13:33:17 2013 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
Wed Nov 13 13:33:17 2013 open_tun, tt->ipv6=0
Wed Nov 13 13:33:17 2013 TAP-WIN32 device [Local Area Connection] opened: \\.\Global\{862F9A8F-333E-4D66-BCDD-69AD78B819F8}.tap
Wed Nov 13 13:33:17 2013 TAP-Windows Driver Version 9.9
Wed Nov 13 13:33:17 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 10.8.0.6/255.255.255.252 on interface {862F9A8F-333E-4D66-BCDD-69AD78B819F8} [DHCP-serv: 10.8.0.5, lease-time: 31536000]
Wed Nov 13 13:33:17 2013 Successful ARP Flush on interface [37] {862F9A8F-333E-4D66-BCDD-69AD78B819F8}
Wed Nov 13 13:33:22 2013 TEST ROUTES: 1/1 succeeded len=1 ret=1 a=0 u/d=up
Wed Nov 13 13:33:22 2013 C:\Windows\system32\route.exe ADD 10.8.0.1 MASK 255.255.255.255 10.8.0.5
Wed Nov 13 13:33:22 2013 ROUTE: CreateIpForwardEntry succeeded with dwForwardMetric1=30 and dwForwardType=4
Wed Nov 13 13:33:22 2013 Route addition via IPAPI succeeded [adaptive]
Wed Nov 13 13:33:22 2013 Initialization Sequence Completed
server route command
===========================================================================
Interface List
29...00 ff 53 6b 08 fd ......TAP-Windows Adapter V9
3...90 2b 34 dd 74 c2 ......Qualcomm Atheros AR8161 PCI-E Gigabit Ethernet Controller (NDI
1...........................Software Loopback Interface 1
7...00 00 00 00 00 00 00 e0 Teredo Tunneling Pseudo-Interface
6...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #3
17...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #4
===========================================================================
IPv4 Route Table
===========================================================================
Active Routes:
Network Destination Netmask Gateway Interface Metric
0.0.0.0 0.0.0.0 192.168.23.1 192.168.23.99 276
10.8.0.0 255.255.255.0 On-link 10.8.0.1 31
10.8.0.0 255.255.255.0 10.8.0.2 10.8.0.1 30
10.8.0.0 255.255.255.252 On-link 10.8.0.1 286
10.8.0.1 255.255.255.255 On-link 10.8.0.1 286
10.8.0.3 255.255.255.255 On-link 10.8.0.1 286
10.8.0.255 255.255.255.255 On-link 10.8.0.1 286
127.0.0.0 255.0.0.0 On-link 127.0.0.1 306
127.0.0.1 255.255.255.255 On-link 127.0.0.1 306
127.255.255.255 255.255.255.255 On-link 127.0.0.1 306
192.168.23.0 255.255.255.0 On-link 192.168.23.99 276
192.168.23.99 255.255.255.255 On-link 192.168.23.99 276
192.168.23.255 255.255.255.255 On-link 192.168.23.99 276
224.0.0.0 240.0.0.0 On-link 127.0.0.1 306
224.0.0.0 240.0.0.0 On-link 192.168.23.99 276
224.0.0.0 240.0.0.0 On-link 10.8.0.1 286
255.255.255.255 255.255.255.255 On-link 127.0.0.1 306
255.255.255.255 255.255.255.255 On-link 192.168.23.99 276
255.255.255.255 255.255.255.255 On-link 10.8.0.1 286
client route command
IPv4 Route Table
===========================================================================
Active Routes:
Network Destination Netmask Gateway Interface Metric
0.0.0.0 0.0.0.0 192.168.100.1 192.168.100.3 25
10.8.0.1 255.255.255.255 10.8.0.5 10.8.0.6 30
10.8.0.4 255.255.255.252 On-link 10.8.0.6 286
10.8.0.6 255.255.255.255 On-link 10.8.0.6 286
10.8.0.7 255.255.255.255 On-link 10.8.0.6 286
127.0.0.0 255.0.0.0 On-link 127.0.0.1 306
127.0.0.1 255.255.255.255 On-link 127.0.0.1 306
127.255.255.255 255.255.255.255 On-link 127.0.0.1 306
192.168.100.0 255.255.255.0 On-link 192.168.100.3 281
192.168.100.3 255.255.255.255 On-link 192.168.100.3 281
192.168.100.255 255.255.255.255 On-link 192.168.100.3 281
224.0.0.0 240.0.0.0 On-link 127.0.0.1 306
224.0.0.0 240.0.0.0 On-link 192.168.100.3 281
224.0.0.0 240.0.0.0 On-link 10.8.0.6 286
255.255.255.255 255.255.255.255 On-link 127.0.0.1 306
255.255.255.255 255.255.255.255 On-link 192.168.100.3 281
255.255.255.255 255.255.255.255 On-link 10.8.0.6 286
===========================================================================