Background
I have an SSTP VPN with a self-signed certificate. It's running on a physical instance of Server 2008 R2 on our LAN. Three off-network workstations are scheduled to connect to the VPN "at system startup" in Task Scheduler.
C:\Windows\system32\rasman.exe -d "VPN Connection"
Normally, this works without a hitch. I can reboot any of the machines, and the connection gets made.
Problem
The only time the connection fails is when the machines perform their nightly reboot at 2:45 AM. The reboot is another task in Task Scheduler:
C:\Windows\system32\shutdown.exe -r -t 0
After that reboot, Event Viewer shows groups of two errors:
RasClient event 20227
The user SYSTEM dialed a connection named VPN Connection which has failed. The error code returned on failure is -2147014836.
RasSstp event 1
The initial Secure Socket Tunneling Protocol request could not be successfully sent to the server. This can be due to network connectivity issues or certificate (trust) issues. The detailed error message is provided below. Correct the problem and try again.
A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
Troubleshooting
What mystifies me is why the connection fails only at night. I've tested the scheduled reboot during the day, and the connection always succeeds. I've checked the connection settings and dialed manually, and again, it succeeds. That's made me wonder if some component of the network is unavailable at night, as the RasSstp event description suggests. However:
- The server's event logs show that it's awake and behaving normally at 2:45 AM. The logs don't mention anything about getting a connection request, though.
- The components of the network connection (router, wireless antennas, firewall, router, and switch to server) have no scheduled downtime. Maybe they're failing for some other reason, but it seems like some other device of our roughly 200 would be complaining too if that were the case.
- Search results for error -2147014836 focus on Windows Azure, which we aren't using. The VPN server is a physical server on our LAN.
- Search results for RasClient event 202227 focus on problems with making a connection, period. Our connection already works most of the time.
Question
Has anyone else has had this kind of error? Is there something besides a networking hiccup that could be causing this? Your help is much appreciated!
