Deploy Fails on Deploy Octopus Deployment Tools

Tyler deploy fails on the Deploy Octopus Deployment Tools step with the following error:

The step failed: Activity Deploy Octopus Deployment Tools on TylerServer failed with error 'A request was sent to a polling endpoint, the polling endpoint collected it but did not respond in the allowed time (00:05:00), so the request timed out. Server exception: System.TimeoutException: A request was sent to a polling endpoint, the polling endpoint collected it but did not respond in the allowed time (00:05:00), so the request timed out.'.

• Tyler Deploy
• Update
• System Administration

Tyler Deploy Octopus Tentacle is offline, non-existent, or needs to be redeployed.

1. Connect to the server mentioned in the error of the deployment failure as tylerservice or equivalent
2. Open Services
3. Scroll down to the OctopusDeploy Tentacle service
4. Right-click the service name
5. Click Start if the service is stopped, or Restart if it's already running
6. Return to Tyler Deploy
7. Click on Infrastructure Management
8. Scroll down to the server mentioned in the error in the deployment
9. Click on Check Health
   1. If successful, the connection test should come back as Octopus was able to communicate with machine at...
      1. If the health check comes back as healthy, rerun the deployment
   2. If unsuccessful, it will say Unable to connect to this machine or There was a problem communicating with this machine 
      1. If the health check comes back as unhealthy, there is still an issue connecting to the tentacle
      2. Sometimes a server reboot resolves connection issues between the Octopus Tentacle and Tyler Deploy
      1. If the check health continues to fail, verify the required TCP Firewall Ports are open on the server
         1. Octopus Tentacle Network Requirements

If you need additional assistance, please contact Tyler Systems Management Support or log a case via the Online Support Client Portal.

Tyler Deploy Unable to Connect to This Machine