The problem Landscape have in this case is that connection will fail if
the certificate bundle in /etc/ssl/certs/ca-certificates.conf do not
contain the CA certificate required to validate the one presented by
https://landscape.canonical.com.  In fact, this is not restricted to
Landscape but generalized to any software that depend on the certificate
bundle from ca-certificates.  For example, doing "wget
https://landscape.canonical.com"; will also fail in these cases.

The quick and dirty solution is to reconfigure ca-certificates with:

    sudo dpkg-reconfigure ca-certificates


I am unsure which CA certificate is required to validate 
https://landscape.canonical.com, so I selected all of them in the second dialog 
("Select certificates to activate").   And it work: configure-landscape 
complete just fine then.

-- 
update-ca-certificates error. ca-certificates.crt empty
https://bugs.launchpad.net/bugs/153625
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