I'm not sure you're running the latest version of Checkbox (you can
check with `dpkg -l | grep checkbox` - it should be 0.7) as the md5
warning in your log was addressed in 0.7. If it's not, can you upgrade
and retest?

Also can you check the value of http_proxy (`echo $http_proxy`) - if
you're using the Network Proxy application in the System > Preferences
menu, then that should be being set. If you've not used that
application, how are you setting the system-wide proxy?

If http_proxy is set correctly, then Checkbox should be using it.

-- 
ubuntu system testing tool ignores system proxy settings, and try to submit 
report via direct connection
https://bugs.launchpad.net/bugs/345548
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