Puppet 5.5.16 and prior had a long standing bug that prevented the agent from using a proxy when the HTTP_PROXY environment variable or http_proxy_host puppet setting were defined. This issue, and number of other http proxy issues, were fixed in 5.5.17, 6.4.4 and 6.8.0, so the agent now correctly observes those variables/settings. However, it means puppet may try to use an http proxy when connecting to the puppetserver.
In many environments, an http proxy is configured to only allow connections from internal hosts to external hosts, and it will reject any attempt to "reflect" off of the proxy from an internal host to another internal host. In these environments, puppet agents may no longer be able to connect to its puppetserver after upgrading to 5.5.17, 6.4.4 or 6.8.0+. And since the agent can't get a catalog, you can't use puppet to remedy the issue.
Josh
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Josh Cooper | Software Engineer