Starting the service on Windows Server 2019 often fails

[irwir]

The main issue now is that openvpnserv2 starts after install, but usually fails to start on reboot.

Event log has no NRPT-related entry, the record just states:

Error Service Control Manager 7009 None
A timeout was reached (30000 milliseconds) while waiting for the OpenVPNService service to connect.

Service could be started manually, then it keeps working until reboot.

Previously, the workaround was configuring one restart after failure in service properties; now it might not help too - at least, not every time.
For example, the service did not start after two reboots after installation, but started after installing Tuesday's Windows updates.

It seems some service dependency should be added to ensure successful start every time.

[cron2]

Since openvpnserv2 has no idea about DNS or NRPT, looking for NRPT-related entries won't enlighten us much. Please look for openvpnserv2 related entries.

[irwir]

The generalized issue is: on boot OpenVPN often fails to start. This began several versions ago.

Apparently there was more than one reason, and hence mixup when copying part of the report from other repository.
Missing NRPT registry keys caused crash in openvpnserv (it could be started as SYSTEM).
No such crashes now, but unsuccessful starts of OpenVPN still continued.
There are no other related entries in the event log; manual start is always going well.
What should be fixed now?

[irwir]

Beta 2 also failed to start the service.
Before the service error record in the Event log, there is only one other error - with event ID 12:
The driver detected an internal driver error on \Device\VBoxNetLwf.
Forum topic ID Event 12 for VBoxNetLwf suggested to disregard these records, however on page 4 someone claimed that disabling IPv6 for OpenVPN TAP adapter helped.

Detailed log of service start sequence might help to resolve this issue.

[lstipakov]

It is not possible to debug this without any information. Anything in logs why service cannot be started?

[irwir]

It is not possible to debug this without any information. Anything in logs why service cannot be started?

This is exactly why extended logging or trace was requested above.

Installed is TAP adapter, no GUI - only service, both services configured to be started automatically.
DCO is unavalable for this OS.
Automatic start failed with event IDs 7009, then 7000.
Log in Program Data was not even rewritten on boot, the one after previous successful manual start remained, time stamp unchanged.
Manual start always works.

[lstipakov]

I just tested beta3 with DCO disabled (as in reports) and for me it works:

PS C:\Users\lev> Get-WinEvent -LogName Application | Where-Object { $_.ProviderName -eq 'OpenVPNService' }

   ProviderName: OpenVpnService

TimeCreated                     Id LevelDisplayName Message
-----------                     -- ---------------- -------
26/10/2025 11:05:01              0 Información      Started polling for OpenVPN process, PID 7400
26/10/2025 11:05:01              0 Información      Service started successfully.
26/10/2025 11:05:01              0 Información      Started monitoring OpenVPN process, PID 7400
26/10/2025 11:05:01              0 Información      Read from iservice: 0x00000000 0x00001ce8
26/10/2025 11:05:01              0 Información      Sent startupInfo to iservice
26/10/2025 11:05:01              0 Información      Connecting to iservice pipe...

@irwir Could you double-check your event log and see if there is anything related to OpenVPN?

[irwir]

@lstipakov

Automatic start failed

Manual start always works.

You have tested manual start; nothing was expected to go wrong.
The service fails at boot time only, and all available data had been posted already.

This is exactly why extended logging or trace was requested above.

Repeating this once again. The service should log events during boot, when neither command line nor VS debugger are usable; and the standard text log seems have not been even touched in case of failure.

[irwir]

A wild guess might be that C# runtime takes too much time to get loaded.

[lstipakov]

You have tested manual start;

What makes you think so? I booted the machine.

The service does log its operations (see above) and failures to Event Log.

[irwir]

Remark for you starting the service manually was incorrect.

For example, Windows logged event ID 7009 at 26.09.2025 18:31:21, event ID 7000 one second later.
Lines around this time if running your powershell command:

26.09.2025 19:22:29 0 Information Service started successfully.
26.09.2025 19:22:29 0 Information Started polling for OpenVPN process, PID 5308
26.09.2025 19:22:29 0 Information Started monitoring OpenVPN process, PID 5308
26.09.2025 19:22:29 0 Information Read from iservice: 0x00000000 0x000014bc
26.09.2025 19:22:29 0 Information Sent startupInfo to iservice
26.09.2025 19:22:29 0 Information Connecting to iservice pipe...
26.09.2025 18:29:25 0 Information Service has been successfully shut down.

There is nothing between shutdown and the events - always the same way.
Should be failing before opening the service text log.

Later had to start it manually using LAN connection from another computer.