OctopusDeploy service fails to start after reboot

We automatically reboot our servers every Monday morning at 1:00 AM, and I’ve had a consistent problem with the OctopusDeploy service not starting. (We rolled out Octopus in the last month)
The OctopusServer logs doesn’t have any entries:

2017-09-11 00:13:35.7172 7468 90 INFO https://s-ws101hq:10933/ 90 Secure connection established. Server at ******
2017-09-11 08:47:21.4806 5560 1 INFO Octopus.Server.exe version 3.15.8 ******

At 1:08 AM there is 2 Windows Event log entries:
Event 7009: A timeout was reached (30000 milliseconds) while waiting for the OctopusDeploy service to connect.
Event 7000: The OctopusDeploy service failed to start due to the following error: The service did not respond to the start or control request in a timely fashion.

The Service starts manually without a problem.
The service is set to Startup type: Automatic (Delayed Start), and runs as Local System

Is there any additional logging I can enable?

Hi Sean,

Thanks for getting in touch! It looks like you are affected by the following issue: https://github.com/OctopusDeploy/Issues/issues/2375

It is a long thread, but the short version is that sometimes the .NET CLR has not finished loading before the Tentacle tries to start, thus timing out the Tentacle connection.

The following documentation may provide useful for working around this issue until we can find a way to fix it. It is also linked to at the bottom of that GitHub issue thread.

Let me know if this helps the startup of your service next reboot. Or if you have any further questions at all, please feel free to throw them my way.

Best regards,

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