I can't be sure yet but I got one of the clients to give me a log file.
Looks like the TLS reneg is tripping up:
Mon Aug 06 09:50:43 2012 Initialization Sequence Completed
Mon Aug 06 10:50:31 2012 TLS: soft reset sec=0 bytes=250987949/0 pkts=263016/0
Mon Aug 06 10:52:08 2012 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Mon Aug 06 10:52:08 2012 TLS Error: TLS handshake failed
Mon Aug 06 10:52:08 2012 TLS: move_session: dest=TM_LAME_DUCK src=TM_ACTIVE reinit_src=1
That's the end of the signon at 9:50, then the default TLS reneg at 10:50 which then fails. She sent me a copy of the log once she got the disconnected message and it only contained the soft reset line. When I asked for another copy you see the Error almost 2 min later.
The server log is identical (minus the timediff)
Mon Aug 6 09:58:43 2012 us=232852 <client IP>:4594 TUN WRITE [40]
Mon Aug 6 09:58:43 2012 us=285693 <client IP>:4594 NOTE: --mute triggered...
Mon Aug 6 10:47:39 2012 us=422129 <client IP>:4594 524915 variation(s) on previous 10 message(s) suppressed by --mute
Mon Aug 6 10:47:39 2012 us=422327 <client IP>:4594 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Mon Aug 6 10:47:39 2012 us=422355 <client IP>:4594 TLS Error: TLS handshake failed
Mon Aug 6 10:47:39 2012 us=422370 <client IP>:4594 TLS: move_session: dest=TM_LAME_DUCK src=TM_ACTIVE reinit_src=1
What's next on troubleshooting this? I'm not sure upping the reneg time is a good option; I'd like to figure out why it's not performing correctly.
ETA: I just tried this on a test laptop at my desk. 60 minutes later I got prompted for authentication. Is the renegotiation supposed to trigger a user pw prompt? The way the old outgoing vpn is set up, is user key password protected only. This system is a generic user key with AD authentication under it. Is this a byproduct of the reneg or should it be transparent to the user?