Yes, I was not checking the active environment for mender-client. The HTTPS_PROXY is not added to the mender-client environment during the mender-convert process nor when the service launches. Also, to speed up testing i was launching the mender -daemon which does pull the current environment HTTPS_PROXY. The Squid Proxy server setup added a little more confusion as well. Simply put the HTTPS_PROXY needed to be manually added to the Environment of mender-client.service