OpenVPN sometimes fails to bring a TAP interface up

mokk

I noticed that OpenVPN sometimes fails to bring up its TAP network card. I can't tell in what circumstances it happens because I couldn't find ones. 🙁 I may restart OpenVPN several times until its TAP comes up. Sometimes it becomes up from the very first, sometimes it requires several stop/start chores.

Has anyone encountered the same problem?

[deleted]

Post logs, configs, server/client operating systems. Your post is way too vague to even suggest a specific issue!

mokk

Here's my two logs:

SUCCESS:

Thu Feb 14 12:57:19 2013 OpenVPN 2.3.0 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6]
Thu Feb 14 12:57:19 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables
Thu Feb 14 12:57:19 2013 Diffie-Hellman initialized with 2048 bit key
Thu Feb 14 12:57:19 2013 Control Channel Authentication: using 'C:\Program Files\OpenVPN\keys\server\ta.key' as a OpenVPN static key file
Thu Feb 14 12:57:19 2013 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Feb 14 12:57:19 2013 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Feb 14 12:57:19 2013 Socket Buffers: R=[65536->65536] S=[65536->65536]
Thu Feb 14 12:57:19 2013 ROUTE_GATEWAY 10.2.3.1/255.255.255.0 I=12 HWADDR=00:1a:4d:53:ba:9b
Thu Feb 14 12:57:19 2013 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
Thu Feb 14 12:57:19 2013 open_tun, tt->ipv6=0
Thu Feb 14 12:57:19 2013 TAP-WIN32 device [Groß Anschluß Θ] opened: \\.\Global\{5580FFED-1804-4409-B0B3-5ABC9411BB7D}.tap
Thu Feb 14 12:57:19 2013 TAP-Windows Driver Version 9.9 
Thu Feb 14 12:57:19 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 192.168.137.1/255.255.255.252 on interface {5580FFED-1804-4409-B0B3-5ABC9411BB7D} [DHCP-serv: 192.168.137.2, lease-time: 31536000]
Thu Feb 14 12:57:19 2013 Sleeping for 10 seconds...
Thu Feb 14 12:57:29 2013 Successful ARP Flush on interface [18] {5580FFED-1804-4409-B0B3-5ABC9411BB7D}
Thu Feb 14 12:57:29 2013 C:\Windows\system32\route.exe ADD 10.2.40.0 MASK 255.255.255.0 192.168.137.2
Thu Feb 14 12:57:29 2013 Route addition via IPAPI succeeded <-- THE INTERFACE IS UP
Thu Feb 14 12:57:29 2013 C:\Windows\system32\route.exe ADD 192.168.137.0 MASK 255.255.255.0 192.168.137.2
Thu Feb 14 12:57:29 2013 Route addition via IPAPI succeeded
Thu Feb 14 12:57:29 2013 UDPv4 link local (bound): [undef]
Thu Feb 14 12:57:29 2013 UDPv4 link remote: [undef]
Thu Feb 14 12:57:29 2013 MULTI: multi_init called, r=256 v=256
Thu Feb 14 12:57:29 2013 IFCONFIG POOL: base=192.168.137.4 size=62, ipv6=0
Thu Feb 14 12:57:29 2013 ifconfig_pool_read(), in='mumu,192.168.137.4', TODO: IPv6
Thu Feb 14 12:57:29 2013 succeeded -> ifconfig_pool_set()
Thu Feb 14 12:57:29 2013 IFCONFIG POOL LIST
Thu Feb 14 12:57:29 2013 mumu,192.168.137.4
Thu Feb 14 12:57:29 2013 Initialization Sequence Completed

FAILURE:

Thu Feb 14 03:47:26 2013 OpenVPN 2.3.0 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6]
Thu Feb 14 03:47:26 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables
Thu Feb 14 03:47:26 2013 Diffie-Hellman initialized with 2048 bit key
Thu Feb 14 03:47:26 2013 Control Channel Authentication: using 'C:\Program Files\OpenVPN\keys\server\ta.key' as a OpenVPN static key file
Thu Feb 14 03:47:26 2013 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Feb 14 03:47:26 2013 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Feb 14 03:47:26 2013 Socket Buffers: R=[65536->65536] S=[65536->65536]
Thu Feb 14 03:47:26 2013 ROUTE_GATEWAY 10.2.3.1/255.255.255.0 I=12 HWADDR=00:1a:4d:53:ba:9b
Thu Feb 14 03:47:26 2013 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
Thu Feb 14 03:47:26 2013 open_tun, tt->ipv6=0
Thu Feb 14 03:47:26 2013 TAP-WIN32 device [Groß Anschluß Θ] opened: \\.\Global\{5580FFED-1804-4409-B0B3-5ABC9411BB7D}.tap
Thu Feb 14 03:47:26 2013 TAP-Windows Driver Version 9.9 
Thu Feb 14 03:47:26 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 192.168.137.1/255.255.255.252 on interface {5580FFED-1804-4409-B0B3-5ABC9411BB7D} [DHCP-serv: 192.168.137.2, lease-time: 31536000]
Thu Feb 14 03:47:26 2013 Sleeping for 10 seconds...
Thu Feb 14 03:47:36 2013 Successful ARP Flush on interface [18] {5580FFED-1804-4409-B0B3-5ABC9411BB7D}
Thu Feb 14 03:47:36 2013 C:\Windows\system32\route.exe ADD 10.2.40.0 MASK 255.255.255.0 192.168.137.2
Thu Feb 14 03:47:36 2013 Warning: route gateway is not reachable on any active network adapters: 192.168.137.2 <-- IT'S BECAUSE THE INTERFACE IS DOWN
Thu Feb 14 03:47:36 2013 Route addition via IPAPI failed <-- IT'S BECAUSE THE INTERFACE IS DOWN
Thu Feb 14 03:47:36 2013 C:\Windows\system32\route.exe ADD 192.168.137.0 MASK 255.255.255.0 192.168.137.2
Thu Feb 14 03:47:36 2013 Warning: route gateway is not reachable on any active network adapters: 192.168.137.2 <-- IT'S BECAUSE THE INTERFACE IS DOWN
Thu Feb 14 03:47:36 2013 Route addition via IPAPI failed <-- IT'S BECAUSE THE INTERFACE IS DOWN
Thu Feb 14 03:47:36 2013 UDPv4 link local (bound): [undef]
Thu Feb 14 03:47:36 2013 UDPv4 link remote: [undef]
Thu Feb 14 03:47:36 2013 MULTI: multi_init called, r=256 v=256
Thu Feb 14 03:47:36 2013 IFCONFIG POOL: base=192.168.137.4 size=62, ipv6=0
Thu Feb 14 03:47:36 2013 ifconfig_pool_read(), in='mumu,192.168.137.4', TODO: IPv6
Thu Feb 14 03:47:36 2013 succeeded -> ifconfig_pool_set()
Thu Feb 14 03:47:36 2013 IFCONFIG POOL LIST
Thu Feb 14 03:47:36 2013 mumu,192.168.137.4
Thu Feb 14 03:47:36 2013 Initialization Sequence Completed

mokk

Here's another failure log. Previous logs were server logs, and this one is a client log:

Mon Feb 18 15:16:39 2013 OpenVPN 2.3.0 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6]
Mon Feb 18 15:16:39 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables
Mon Feb 18 15:16:39 2013 Control Channel Authentication: using 'C:\Program Files\OpenVPN\keys\client2\ta.key' as a OpenVPN static key file
Mon Feb 18 15:16:39 2013 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 15:16:39 2013 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 15:16:39 2013 Socket Buffers: R=[65536->65536] S=[65536->65536]
Mon Feb 18 15:16:39 2013 UDPv4 link local: [undef]
Mon Feb 18 15:16:39 2013 UDPv4 link remote: [AF_INET]10.2.100.222:1294
Mon Feb 18 15:16:39 2013 TLS: Initial packet from [AF_INET]10.2.100.222:1294, sid=588f05c1 ee5d7d6b
Mon Feb 18 15:16:39 2013 VERIFY OK: depth=1, C=MU, ST=MUMUTOWN, L=Mumuland, O=NetworkTwo, OU=NetworkTwoNet, CN=NetworkTwo, name=NetworkTwo, emailAddress=admin@NetworkTwo.local
Mon Feb 18 15:16:39 2013 Validating certificate key usage
Mon Feb 18 15:16:39 2013 ++ Certificate has key usage  00a0, expects 00a0
Mon Feb 18 15:16:39 2013 VERIFY KU OK
Mon Feb 18 15:16:39 2013 Validating certificate extended key usage
Mon Feb 18 15:16:39 2013 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
Mon Feb 18 15:16:39 2013 VERIFY EKU OK
Mon Feb 18 15:16:39 2013 VERIFY OK: depth=0, C=MU, ST=MUMUTOWN, L=Mumuland, O=NetworkTwo, OU=NetworkTwoNet, CN=ServerTwo, name=ServerTwo, emailAddress=admin@NetworkTwo.local
Mon Feb 18 15:16:39 2013 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
Mon Feb 18 15:16:39 2013 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 15:16:39 2013 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
Mon Feb 18 15:16:39 2013 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 15:16:39 2013 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 2048 bit RSA
Mon Feb 18 15:16:39 2013 [ServerTwo] Peer Connection Initiated with [AF_INET]10.2.100.222:1294
Mon Feb 18 15:16:41 2013 SENT CONTROL [ServerTwo]: 'PUSH_REQUEST' (status=1)
Mon Feb 18 15:16:41 2013 PUSH: Received control message: 'PUSH_REPLY,route 192.168.139.0 255.255.255.0,topology net30,ping 10,ping-restart 120,ifconfig 192.168.139.10 192.168.139.9'
Mon Feb 18 15:16:41 2013 OPTIONS IMPORT: timers and/or timeouts modified
Mon Feb 18 15:16:41 2013 OPTIONS IMPORT: --ifconfig/up options modified
Mon Feb 18 15:16:41 2013 OPTIONS IMPORT: route options modified
Mon Feb 18 15:16:41 2013 ROUTE_GATEWAY 10.2.40.1/255.255.255.0 I=18 HWADDR=00:24:1d:c1:02:21
Mon Feb 18 15:16:41 2013 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
Mon Feb 18 15:16:41 2013 open_tun, tt->ipv6=0
Mon Feb 18 15:16:41 2013 TAP-WIN32 device [Groß Anschluß Θ] opened: \\.\Global\{528CB6D8-30F7-4F03-9CC5-3EB79D66D0B1}.tap
Mon Feb 18 15:16:41 2013 TAP-Windows Driver Version 9.9 
Mon Feb 18 15:16:41 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 192.168.139.10/255.255.255.252 on interface {528CB6D8-30F7-4F03-9CC5-3EB79D66D0B1} [DHCP-serv: 192.168.139.9, lease-time: 31536000]
Mon Feb 18 15:16:44 2013 Successful ARP Flush on interface [20] {528CB6D8-30F7-4F03-9CC5-3EB79D66D0B1}
Mon Feb 18 15:16:51 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down <-- THE NETWORK INTERFACE IS DOWN
Mon Feb 18 15:16:51 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:16:55 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:16:55 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:16:56 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:16:56 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:16:57 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:16:57 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:16:58 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:16:58 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:16:59 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:16:59 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:00 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:00 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:01 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:01 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:02 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:02 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:03 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:03 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:04 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:04 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:05 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:05 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:06 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:06 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:07 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:07 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:08 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:08 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:09 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:09 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:10 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:10 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:11 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:11 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:13 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:13 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:14 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:14 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:15 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:15 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:16 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:16 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:18 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:18 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:19 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:19 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 15:17:20 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 15:17:20 2013 C:\Windows\system32\route.exe ADD 192.168.139.0 MASK 255.255.255.0 192.168.139.9
Mon Feb 18 15:17:20 2013 Warning: route gateway is not reachable on any active network adapters: 192.168.139.9 <-- THE NETWORK INTERFACE IS DOWN
Mon Feb 18 15:17:20 2013 Route addition via IPAPI failed
SYSTEM ROUTING TABLE
0.0.0.0 0.0.0.0 10.2.40.1 p=0 i=18 t=4 pr=3 a=184 h=0 m=266/0/0/0/0
10.0.0.0 255.0.0.0 10.2.40.1 p=0 i=18 t=4 pr=3 a=181 h=0 m=30/0/0/0/0
10.2.40.0 255.255.255.0 10.2.40.153 p=0 i=18 t=3 pr=2 a=181 h=0 m=266/0/0/0/0
10.2.40.153 255.255.255.255 10.2.40.153 p=0 i=18 t=3 pr=2 a=181 h=0 m=266/0/0/0/0
10.2.40.255 255.255.255.255 10.2.40.153 p=0 i=18 t=3 pr=2 a=181 h=0 m=266/0/0/0/0
200.60.128.0 255.255.128.0 10.2.40.1 p=0 i=18 t=4 pr=3 a=181 h=0 m=30/0/0/0/0
127.0.0.0 255.0.0.0 127.0.0.1 p=0 i=1 t=3 pr=2 a=196 h=0 m=306/0/0/0/0
127.0.0.1 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=196 h=0 m=306/0/0/0/0
127.255.255.255 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=196 h=0 m=306/0/0/0/0
224.0.0.0 240.0.0.0 127.0.0.1 p=0 i=1 t=3 pr=2 a=196 h=0 m=306/0/0/0/0
224.0.0.0 240.0.0.0 10.2.40.153 p=0 i=18 t=3 pr=2 a=184 h=0 m=266/0/0/0/0
255.255.255.255 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=196 h=0 m=306/0/0/0/0
255.255.255.255 255.255.255.255 10.2.40.153 p=0 i=18 t=3 pr=2 a=184 h=0 m=266/0/0/0/0
SYSTEM ADAPTER LIST
TAP-Windows Adapter V9
  Index = 20
  GUID = {528CB6D8-30F7-4F03-9CC5-3EB79D66D0B1}
  IP = 169.254.241.226/255.255.0.0 <-- WRONG IP!!! THE IP MUST BE 192.168.139.10/255.255.255.252
  MAC = 00:ff:52:8c:b6:d8
  GATEWAY = [undef]
Realtek PCIe GBE Family Controller #2
  Index = 18
  GUID = {B9FAABE4-24E9-4925-A2FA-9878552628BB}
  IP = 10.2.40.153/255.255.255.0
  MAC = 00:24:1d:c1:02:21
  GATEWAY = 10.2.40.1
  DNS = 10.2.40.5 10.2.40.6
Mon Feb 18 15:17:20 2013 Initialization Sequence Completed With Errors ( see http://openvpn.net/faq.html#dhcpclientserv )

mokk

And another client log:

Mon Feb 18 19:50:38 2013 OpenVPN 2.3.0 [SSL (OpenSSL)] [LZO] [PKCS11] [eurephia] [IPv6]
Mon Feb 18 19:50:38 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables
Mon Feb 18 19:50:38 2013 Control Channel Authentication: using 'C:\Program Files\OpenVPN\keys\client2\ta.key' as a OpenVPN static key file
Mon Feb 18 19:50:38 2013 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 19:50:38 2013 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 19:50:38 2013 Socket Buffers: R=[65536->65536] S=[65536->65536]
Mon Feb 18 19:50:38 2013 UDPv4 link local: [undef]
Mon Feb 18 19:50:38 2013 UDPv4 link remote: [AF_INET]10.2.100.222:1294
Mon Feb 18 19:50:38 2013 TLS: Initial packet from [AF_INET]10.2.100.222:1294, sid=1b345456 955c554a
Mon Feb 18 19:50:38 2013 VERIFY OK: depth=1, C=MU, ST=MUMUTOWN, L=Mumuland, O=NetworkTwo, OU=NetworkTwoNet, CN=NetworkTwo, name=NetworkTwo, emailAddress=admin@NetworkTwo.local
Mon Feb 18 19:50:38 2013 Validating certificate key usage
Mon Feb 18 19:50:38 2013 ++ Certificate has key usage  00a0, expects 00a0
Mon Feb 18 19:50:38 2013 VERIFY KU OK
Mon Feb 18 19:50:38 2013 Validating certificate extended key usage
Mon Feb 18 19:50:38 2013 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
Mon Feb 18 19:50:38 2013 VERIFY EKU OK
Mon Feb 18 19:50:38 2013 VERIFY OK: depth=0, C=MU, ST=MUMUTOWN, L=Mumuland, O=NetworkTwo, OU=NetworkTwoNet, CN=ServerTwo, name=ServerTwo, emailAddress=admin@NetworkTwo.local
Mon Feb 18 19:50:38 2013 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
Mon Feb 18 19:50:38 2013 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 19:50:38 2013 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
Mon Feb 18 19:50:38 2013 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 19:50:38 2013 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 2048 bit RSA
Mon Feb 18 19:50:38 2013 [ServerTwo] Peer Connection Initiated with [AF_INET]10.2.100.222:1294
Mon Feb 18 19:50:40 2013 SENT CONTROL [ServerTwo]: 'PUSH_REQUEST' (status=1)
Mon Feb 18 19:50:40 2013 PUSH: Received control message: 'PUSH_REPLY,route 192.168.139.0 255.255.255.0,topology net30,ping 10,ping-restart 120,ifconfig 192.168.139.6 192.168.139.5'
Mon Feb 18 19:50:40 2013 OPTIONS IMPORT: timers and/or timeouts modified
Mon Feb 18 19:50:40 2013 OPTIONS IMPORT: --ifconfig/up options modified
Mon Feb 18 19:50:40 2013 OPTIONS IMPORT: route options modified
Mon Feb 18 19:50:40 2013 ROUTE_GATEWAY 10.2.3.1/255.255.255.0 I=12 HWADDR=00:1a:4d:53:ba:9b
Mon Feb 18 19:50:40 2013 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
Mon Feb 18 19:50:40 2013 open_tun, tt->ipv6=0
Mon Feb 18 19:50:40 2013 TAP-WIN32 device [Groß Anschluß Θ] opened: \\.\Global\{D285CD93-D17C-4862-97A9-1301D1655CFF}.tap
Mon Feb 18 19:50:40 2013 TAP-Windows Driver Version 9.9 
Mon Feb 18 19:50:40 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 192.168.139.6/255.255.255.252 on interface {D285CD93-D17C-4862-97A9-1301D1655CFF} [DHCP-serv: 192.168.139.5, lease-time: 31536000]
Mon Feb 18 19:50:43 2013 Successful ARP Flush on interface [18] {D285CD93-D17C-4862-97A9-1301D1655CFF}
Mon Feb 18 19:50:49 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down <-- THE NETWORK INTERFACE IS DOWN
Mon Feb 18 19:50:49 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:50:54 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:50:54 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:50:55 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:50:55 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:50:56 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:50:56 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:50:57 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:50:57 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:50:58 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:50:58 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:50:59 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:50:59 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:01 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:01 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:02 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:02 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:03 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:03 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:04 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:04 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:05 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:05 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:06 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:06 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:08 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:08 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:09 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:09 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:10 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:10 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:11 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:11 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:12 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:12 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:13 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:13 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:14 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:14 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:15 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:15 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:16 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:16 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:17 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:17 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:18 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:18 2013 Route: Waiting for TUN/TAP interface to come up...
Mon Feb 18 19:51:19 2013 TEST ROUTES: 0/0 succeeded len=1 ret=0 a=0 u/d=down
Mon Feb 18 19:51:19 2013 C:\Windows\system32\route.exe ADD 192.168.139.0 MASK 255.255.255.0 192.168.139.5
Mon Feb 18 19:51:19 2013 Warning: route gateway is not reachable on any active network adapters: 192.168.139.5
Mon Feb 18 19:51:19 2013 Route addition via IPAPI failed
SYSTEM ROUTING TABLE
0.0.0.0 0.0.0.0 10.2.3.1 p=0 i=12 t=4 pr=3 a=178 h=0 m=10/0/0/0/0
10.2.3.0 255.255.255.0 10.2.3.201 p=0 i=12 t=3 pr=2 a=178 h=0 m=266/0/0/0/0
10.2.3.201 255.255.255.255 10.2.3.201 p=0 i=12 t=3 pr=2 a=178 h=0 m=266/0/0/0/0
10.2.3.255 255.255.255.255 10.2.3.201 p=0 i=12 t=3 pr=2 a=178 h=0 m=266/0/0/0/0
127.0.0.0 255.0.0.0 127.0.0.1 p=0 i=1 t=3 pr=2 a=206 h=0 m=306/0/0/0/0
127.0.0.1 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=206 h=0 m=306/0/0/0/0
127.255.255.255 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=206 h=0 m=306/0/0/0/0
224.0.0.0 240.0.0.0 127.0.0.1 p=0 i=1 t=3 pr=2 a=206 h=0 m=306/0/0/0/0
224.0.0.0 240.0.0.0 10.2.3.201 p=0 i=12 t=3 pr=2 a=183 h=0 m=266/0/0/0/0
255.255.255.255 255.255.255.255 127.0.0.1 p=0 i=1 t=3 pr=2 a=206 h=0 m=306/0/0/0/0
255.255.255.255 255.255.255.255 10.2.3.201 p=0 i=12 t=3 pr=2 a=183 h=0 m=266/0/0/0/0
SYSTEM ADAPTER LIST
TAP-Windows Adapter V9
  Index = 18
  GUID = {D285CD93-D17C-4862-97A9-1301D1655CFF}
  IP = 169.254.24.30/255.255.0.0 <-- WRONG IP!!! THE IP MUST BE 192.168.139.6/255.255.255.252
  MAC = 00:ff:d2:85:cd:93
  GATEWAY = [undef]
Realtek PCIe GBE Family Controller
  Index = 12
  GUID = {8011E520-F298-4C43-8E98-0AA652A4B2C0}
  IP = 10.2.3.201/255.255.255.0
  MAC = 00:1a:4d:53:ba:9b
  GATEWAY = 10.2.3.1
  DHCP SERV = 200.60.100.4
  DNS = 200.60.100.2 200.60.100.3
Mon Feb 18 19:51:19 2013 Initialization Sequence Completed With Errors ( see http://openvpn.net/faq.html#dhcpclientserv )

In all of these cases of failure the network interface was down (Network cable unplugged).

mmilne

try disabling the IPV6 support on Windows TUN/TAP interface. It've solved the "Waiting for TUN/TAP" for my connection