I've been using the OpenVPN GUI in windows 7 (32 bit) for a few years and it's been rock solid - very happy with it. I've just built a windows 8 machine (64 bit) and have tried the 32 bit software (version 2.2.2) as well as the x86/64 version 2.3.1 and the result is flaky. I can connect about half the time, the other half I get errors like this:
Sat Jun 01 09:29:11 2013 TAP-WIN32 device [Local Area Connection] opened: \\.\Global\{B12B1294-1A2E-42D2-8478-BB7F76053AA6}.tap
Sat Jun 01 09:29:11 2013 TAP-Windows Driver Version 9.9
Sat Jun 01 09:29:11 2013 Notified TAP-Windows driver to set a DHCP IP/netmask of 10.8.0.6/255.255.255.252 on interface {B12B1294-1A2E-42D2-8478-BB7F76053AA6} [DHCP-serv: 10.8.0.5, lease-time: 31536000]
Sat Jun 01 09:29:11 2013 Successful ARP Flush on interface [25] {B12B1294-1A2E-42D2-8478-BB7F76053AA6}
Sat Jun 01 09:29:13 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:13 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:16 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:16 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:17 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:17 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:18 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:18 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:19 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:19 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:20 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:20 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:21 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:21 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:23 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:23 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:24 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:24 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:25 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:25 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:26 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:26 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:27 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:27 2013 Route: Waiting for TUN/TAP interface to come up...
Sat Jun 01 09:29:28 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:28 2013 Route: Waiting for TUN/TAP interface to come up...
edited a few lines out here

Sat Jun 01 09:29:44 2013 TEST ROUTES: 0/0 succeeded len=2 ret=0 a=0 u/d=down
Sat Jun 01 09:29:44 2013 MANAGEMENT: >STATE:1370071784,ADD_ROUTES,,,
Sat Jun 01 09:29:44 2013 C:\Windows\system32\route.exe ADD 192.168.55.0 MASK 255.255.255.0 10.8.0.5
Sat Jun 01 09:29:44 2013 env_block: add PATH=C:\Windows\System32;C:\WINDOWS;C:\WINDOWS\System32\Wbem
Sat Jun 01 09:29:44 2013 C:\Windows\system32\route.exe ADD 10.8.0.1 MASK 255.255.255.255 10.8.0.5
Sat Jun 01 09:29:44 2013 env_block: add PATH=C:\Windows\System32;C:\WINDOWS;C:\WINDOWS\System32\Wbem
Sat Jun 01 09:29:44 2013 SYSTEM ROUTING TABLE
The result of the failed attempts is this:
Sat Jun 01 10:02:14 2013 SYSTEM ADAPTER LIST
Sat Jun 01 10:02:14 2013 TAP-Windows Adapter V9
Sat Jun 01 10:02:14 2013 Index = 25
Sat Jun 01 10:02:14 2013 GUID = {B12B1294-1A2E-42D2-8478-BB7F76053AA6}
Sat Jun 01 10:02:14 2013 IP = 0.0.0.0/0.0.0.0
Sat Jun 01 10:02:14 2013 MAC = 00:ff:b1:2b:12:94
Sat Jun 01 10:02:14 2013 GATEWAY = 0.0.0.0/255.255.255.255
Sat Jun 01 10:02:14 2013 DHCP SERV =
Sat Jun 01 10:02:14 2013 DHCP LEASE OBTAINED = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DHCP LEASE EXPIRES = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 PRI WINS = 192.168.55.13/255.255.255.255
Sat Jun 01 10:02:14 2013 SEC WINS =
Sat Jun 01 10:02:14 2013 DNS SERV =
Sat Jun 01 10:02:14 2013 Juniper Network Connect Virtual Adapter
Sat Jun 01 10:02:14 2013 Index = 23
Sat Jun 01 10:02:14 2013 GUID = {85D35DFA-A1E4-428E-8CF4-C99E9A50275B}
Sat Jun 01 10:02:14 2013 IP = 0.0.0.0/0.0.0.0
Sat Jun 01 10:02:14 2013 MAC = 00:ff:10:f0:51:05
Sat Jun 01 10:02:14 2013 GATEWAY = 0.0.0.0/255.255.255.255
Sat Jun 01 10:02:14 2013 DHCP SERV =
Sat Jun 01 10:02:14 2013 DHCP LEASE OBTAINED = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DHCP LEASE EXPIRES = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DNS SERV =
Sat Jun 01 10:02:14 2013 Bluetooth Device (Personal Area Network)
Sat Jun 01 10:02:14 2013 Index = 15
Sat Jun 01 10:02:14 2013 GUID = {90413427-FAD1-4DA5-8D3A-5E973F67C45A}
Sat Jun 01 10:02:14 2013 IP = 0.0.0.0/0.0.0.0
Sat Jun 01 10:02:14 2013 MAC = 00:1e:37:e6:98:c8
Sat Jun 01 10:02:14 2013 GATEWAY = 0.0.0.0/255.255.255.255
Sat Jun 01 10:02:14 2013 DHCP SERV =
Sat Jun 01 10:02:14 2013 DHCP LEASE OBTAINED = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DHCP LEASE EXPIRES = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DNS SERV =
Sat Jun 01 10:02:14 2013 Realtek PCIe GBE Family Controller
Sat Jun 01 10:02:14 2013 Index = 13
Sat Jun 01 10:02:14 2013 GUID = {A57A60A8-DADE-4E52-AFA6-33463EB26D7D}
Sat Jun 01 10:02:14 2013 IP = 0.0.0.0/0.0.0.0
Sat Jun 01 10:02:14 2013 MAC = 00:1e:68:50:b0:fe
Sat Jun 01 10:02:14 2013 GATEWAY = 0.0.0.0/255.255.255.255
Sat Jun 01 10:02:14 2013 DHCP SERV =
Sat Jun 01 10:02:14 2013 DHCP LEASE OBTAINED = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DHCP LEASE EXPIRES = Sat Jun 01 10:02:14 2013
Sat Jun 01 10:02:14 2013 DNS SERV =
Sat Jun 01 10:02:14 2013 Intel(R) PRO/Wireless 3945ABG Network Connection
Sat Jun 01 10:02:14 2013 Index = 12
Sat Jun 01 10:02:14 2013 GUID = {89DBBDD5-4793-47D2-BEC0-9D8C90541B37}
Sat Jun 01 10:02:14 2013 IP = 10.10.10.55/255.255.255.0
Sat Jun 01 10:02:14 2013 MAC = 00:1f:3c:25:a6:e9
Sat Jun 01 10:02:14 2013 GATEWAY = 10.10.10.1/255.255.255.255
Sat Jun 01 10:02:14 2013 DHCP SERV = 10.10.10.1/255.255.255.255
Sat Jun 01 10:02:14 2013 DHCP LEASE OBTAINED = Sat Jun 01 09:45:32 2013
Sat Jun 01 10:02:14 2013 DHCP LEASE EXPIRES = Tue Jun 04 09:45:32 2013
Sat Jun 01 10:02:14 2013 DNS SERV = 10.10.10.1/255.255.255.255
Sat Jun 01 10:02:14 2013 VMware Virtual Ethernet Adapter for VMnet1
Sat Jun 01 10:02:14 2013 Index = 20
Sat Jun 01 10:02:14 2013 GUID = {2CAC0C6D-954C-4FF1-BBCA-95B15A447850}
Sat Jun 01 10:02:14 2013 IP = 192.168.31.1/255.255.255.0
Sat Jun 01 10:02:14 2013 MAC = 00:50:56:c0:00:01
Sat Jun 01 10:02:14 2013 GATEWAY = 0.0.0.0/255.255.255.255
Sat Jun 01 10:02:14 2013 DNS SERV =
Sat Jun 01 10:02:14 2013 VMware Virtual Ethernet Adapter for VMnet8
Sat Jun 01 10:02:14 2013 Index = 21
Sat Jun 01 10:02:14 2013 GUID = {651DE73A-CA16-40F8-B870-D25EA557E9D6}
Sat Jun 01 10:02:14 2013 IP = 192.168.233.1/255.255.255.0
Sat Jun 01 10:02:14 2013 MAC = 00:50:56:c0:00:08
Sat Jun 01 10:02:14 2013 GATEWAY = 0.0.0.0/255.255.255.255
Sat Jun 01 10:02:14 2013 DNS SERV =
Sat Jun 01 10:02:14 2013 Initialization Sequence Completed With Errors ( see http://openvpn.net/faq.html#dhcpclientserv )
Sat Jun 01 10:02:14 2013 MANAGEMENT: >STATE:1370073734,CONNECTED,ERROR,10.8.0.6,41.134.129.90
So the failed attempts end up not providing any IP address or getting and server IP addresses (see bolded text above). When I do a 'reconnect' I can usually get back in with a valid IP and I'm not changing any config here, just have to try a few times until I get an IP.
In windows 7 this was very stable - is this a problem associated with windows 8 or the fact that I have VMware Workstation installed?
Any assistance is appreciated, thanks.