Registration fails if octopus is uninstalled and reinstalled

[spuder]

If you uninstall the tentacle and delete the cert, then try and run chef, the installation/registration will fail with error: See this gist for full chef error

Octopus logs

2016-08-16 20:09:47.2058      7 FATAL  No certificate has been generated for this Tentacle. Please run the new-certificate command before starting.

The octopus logs are a bit misleading since the cert has been generated, it just wasn't imported because the cert was generated with the -e flag.

 -e, --export-file=VALUE    Exports a new certificate to the specified file
                               as unprotected base64 text, but does not save it
                               to the Tentacle configuration; for use with the
                               import-certificate command

Cause

There are multiple factors that create the code path that causes this problem

• Uninstalling octopus tentacle does not remove the windows service (it still shows up in services.msc, but is disabled. Possibly a bug in octopus msi)
• The cookbook has 2 resources that generate and register a cert. The registration gets skipped because the service still exists, triggering guard interpreter: not_if { ::Win32::Service.exists?(service_name) }

https://github.com/cvent/octopus-deploy-cookbook/blob/master/providers/tentacle.rb#L131

• Because the generate cert command uses the -e option, the cert is only generated, not registered.

Work Around

Manually delete windows service before attempting to run chef

Possible Solutions

• Combine cert generate & cert register into 1 resource
• Change the guard interpreter to something other than ::Win32::Service.exists?(service_name)
• Avoid using the -e option so the cert is automatically registered when generated (might require reordering resources so the tentacle is created before cert is generated)
• Ignore this problem & document the steps to avoid this code path.

[spuder]

I've opened a bug ticket with octopus.

http://help.octopusdeploy.com/discussions/problems/47072-uninstall-doesnt-remove-service

[brentm5]

I know with 3.2.24 which is the one that is in the test cookbook with windows 2008R2 this does in fact work as expected. Not sure if anything has changed between then and now or not.

[spuder]

According to octopus Uninstalling octopus tentacle does not remove the windows service is by design. See linked help article