I have also tried pinging 10.8.0.6, which is what the client sees as the DHCP server; no response.
And here is the applicable part of the routing table on the client after connecting to the VPN:
Active Routes:
Network Destination Netmask Gateway Interface Metric
0.0.0.0 0.0.0.0 192.168.1.1 192.168.1.47 2
10.8.0.0 255.255.255.0 10.8.0.6 10.8.0.5 30
10.8.0.4 255.255.255.252 On-link 10.8.0.5 286
10.8.0.5 255.255.255.255 On-link 10.8.0.5 286
10.8.0.7 255.255.255.255 On-link 10.8.0.5 286
And the client log during connection:
Thu Mar 14 12:09:13 2013 OpenVPN 2.2.1 Win32-MSVC++ [SSL] [LZO2] built on Jul 1 2011
Thu Mar 14 12:09:13 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables
Thu Mar 14 12:09:13 2013 Control Channel Authentication: using 'XXXXXXXXXXXXXXXXXXXXX' as a OpenVPN static key file
Thu Mar 14 12:09:13 2013 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Mar 14 12:09:13 2013 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Mar 14 12:09:13 2013 LZO compression initialized
Thu Mar 14 12:09:13 2013 Control Channel MTU parms [ L:1542 D:166 EF:66 EB:0 ET:0 EL:0 ]
Thu Mar 14 12:09:13 2013 Socket Buffers: R=[8192->8192] S=[8192->8192]
Thu Mar 14 12:09:13 2013 Data Channel MTU parms [ L:1542 D:1450 EF:42 EB:135 ET:0 EL:0 AF:3/1 ]
Thu Mar 14 12:09:13 2013 Local Options hash (VER=V4): '504e774e'
Thu Mar 14 12:09:13 2013 Expected Remote Options hash (VER=V4): '14168603'
Thu Mar 14 12:09:13 2013 UDPv4 link local: [undef]
Thu Mar 14 12:09:13 2013 UDPv4 link remote: XXXXXXXXXXXXXXXXXXXXX
Thu Mar 14 12:09:13 2013 TLS: Initial packet from XXXXXXXXXXXXXXXXXXXXX, sid=afcf3f83 d0c9060b
Thu Mar 14 12:09:13 2013 VERIFY OK: depth=1, /C=US/ST=OH/XXXXXXXXXXXXXXXXXXXXX
Thu Mar 14 12:09:13 2013 VERIFY OK: nsCertType=SERVER
Thu Mar 14 12:09:13 2013 VERIFY OK: depth=0, /C=US/ST=OH/XXXXXXXXXXXXXXXXXXXXX
Thu Mar 14 12:09:14 2013 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
Thu Mar 14 12:09:14 2013 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Mar 14 12:09:14 2013 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
Thu Mar 14 12:09:14 2013 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
Thu Mar 14 12:09:14 2013 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 1024 bit RSA
Thu Mar 14 12:09:14 2013 [CROWLAP1] Peer Connection Initiated with XXXXXXXXXXXXXXXXXXXXX
Thu Mar 14 12:09:16 2013 SENT CONTROL [CROWLAP1]: 'PUSH_REQUEST' (status=1)
Thu Mar 14 12:09:16 2013 PUSH: Received control message: 'PUSH_REPLY,route 10.8.0.0 255.255.255.0,topology net30,ping 10,ping-restart 120,ifconfig 10.8.0.5 10.8.0.6'
Thu Mar 14 12:09:16 2013 OPTIONS IMPORT: timers and/or timeouts modified
Thu Mar 14 12:09:16 2013 OPTIONS IMPORT: --ifconfig/up options modified
Thu Mar 14 12:09:16 2013 OPTIONS IMPORT: route options modified
Thu Mar 14 12:09:16 2013 ROUTE default_gateway=192.168.1.1
Thu Mar 14 12:09:16 2013 TAP-WIN32 device [ShrewVPN] opened: \\.\Global\{C641B4B2-66A7-4D0F-AC5B-8A559CA399CC}.tap
Thu Mar 14 12:09:16 2013 TAP-Win32 Driver Version 9.8
Thu Mar 14 12:09:16 2013 TAP-Win32 MTU=1500
Thu Mar 14 12:09:16 2013 Notified TAP-Win32 driver to set a DHCP IP/netmask of 10.8.0.5/255.255.255.252 on interface {C641B4B2-66A7-4D0F-AC5B-8A559CA399CC} [DHCP-serv: 10.8.0.6, lease-time: 31536000]
Thu Mar 14 12:09:16 2013 Successful ARP Flush on interface [15] {C641B4B2-66A7-4D0F-AC5B-8A559CA399CC}
Thu Mar 14 12:09:21 2013 TEST ROUTES: 1/1 succeeded len=1 ret=1 a=0 u/d=up
Thu Mar 14 12:09:21 2013 C:\WINDOWS\system32\route.exe ADD 10.8.0.0 MASK 255.255.255.0 10.8.0.6
Thu Mar 14 12:09:21 2013 ROUTE: CreateIpForwardEntry succeeded with dwForwardMetric1=30 and dwForwardType=4
Thu Mar 14 12:09:21 2013 Route addition via IPAPI succeeded [adaptive]
Thu Mar 14 12:09:21 2013 Initialization Sequence Completed
And the client IPCONFIG for the VPN adapter:
Connection-specific DNS Suffix . :
Description . . . . . . . . . . . : TAP-Win32 Adapter V9
Physical Address. . . . . . . . . : XXXXXXXXXXXXXXX
DHCP Enabled. . . . . . . . . . . : Yes
Autoconfiguration Enabled . . . . : Yes
Link-local IPv6 Address . . . . . : fe80::61a9:1ca1:9d4d:7c97%15(Preferred)
IPv4 Address. . . . . . . . . . . : 10.8.0.5(Preferred)
Subnet Mask . . . . . . . . . . . : 255.255.255.252
Lease Obtained. . . . . . . . . . : Thursday, March 14, 2013 12:09:16 PM
Lease Expires . . . . . . . . . . : Friday, March 14, 2014 12:09:16 PM
Default Gateway . . . . . . . . . :
DHCP Server . . . . . . . . . . . : 10.8.0.6
DHCPv6 IAID . . . . . . . . . . . : 620822470
DHCPv6 Client DUID. . . . . . . . : 00-01-00-01-15-EF-7D-41-10-1F-74-59-A1-08
DNS Servers . . . . . . . . . . . : fec0:0:0:ffff::1%1
fec0:0:0:ffff::2%1
fec0:0:0:ffff::3%1
NetBIOS over Tcpip. . . . . . . . : Enabled