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.

If you are upgrading to 5.5.17, 6.4.4 or 6.8.x, make sure to add the FQDN
of the puppetserver to the NO_PROXY environment variable or no_proxy puppet
setting *before* upgrading. Due to
https://tickets.puppetlabs.com/browse/PUP-9990 the puppetserver's FQDN must
be specified, as opposed to a domain. The ability to specify a domain was
fixed in 6.9.0 and will be backported to 5.5.x and 6.4.x in
https://tickets.puppetlabs.com/browse/PUP-10112.

If upgrading to 6.9.0 or greater, you can specify a dotted domain for the
puppetserver, e.g. no_proxy=localhost,.example.com, and/or the puppetserver
FQDN. However, don't use wildcards (*.example.com) or "bare" domains (
example.com) as puppet and ruby do not consistently handle them. See
https://tickets.puppetlabs.com/browse/PUP-10106, which will be fixed in the
next set of releases.

Josh

-- 
Josh Cooper | Software Engineer
j...@puppet.com | @coopjn

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