pfSense

When pfSense is set to use an upstream proxy with authentication, the update check fails to run from the GUI. It works from the shell.

Proxy authentication is configured under System > Advanced, Miscellaneous tab, and the Proxy URL, Proxy Port, Proxy Username and Proxy Password fields are all filled in and pointed to an active proxy.

When checking for updates from the GUI, it immediately returns that there is no new version. Inspecting the results of the check shows that it failed:

: cat upgrade_log.txt
>>> Updating repositories metadata... failed.

From a shell prompt, updating the metadata shows a new version available:

: /bin/sh /etc/rc.update_pkg_metadata now
: cat upgrade_log.txt 
2.5.0.a.20190415.1201 version of pfSense is available

Manually running an update check also works from the shell:

: pfSense-upgrade -c
>>> Updating repositories metadata... done.
2.5.0.a.20190415.1201 version of pfSense is available

Running the upgrade from the shell also succeeds.

Removing the proxy configuration from the GUI and allowing it to reach out directly also works.