Error pushing packages to clients in a new development domain

We are able to successfully add the machines to the environment

Any packages we push to the new development domain end up failing. We feel it could be due to a delayed response from the client causing the Octopus server to error on the deployment

When we reset the connection from the Octopus server to the client, the time / date of the last connection does not update even though the octopus tentacle service gets recycled due to the reset

Closing as duplicate of