I was having the same problem when trying to install ssl-cert via a
script post-preseed:

chgrp: cannot access `/etc/ssl/private/ssl-cert-snakeoil.key': No such file or 
directory
chmod: cannot access `/etc/ssl/private/ssl-cert-snakeoil.key': No such file or 
directory

The cause seems to be $HOME not being defined. The postinst calls make-
ssl-cert, which uses the template file /usr/share/ssl-cert/ssleay.cnf as
an argument to openssl -req. ssleay.cnf contains:

RANDFILE = $ENV::HOME/.rnd

which naturally breaks when $HOME isn't present. Ideally make-ssl-cert
should either check for $HOME, or perhaps check for errors on the
openssl command rather than sending to /dev/null ?

-- 
ssl-cert (1.0.11.0ubuntu1) postinst is broken
https://bugs.launchpad.net/bugs/43987
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