It fails in an automatic upgrade/installation environment because the PATH 
variables are different than if you're using a shell. /usr/sbin is not included 
if a cron runs the upgrade (or installation) - therefor the command 
"make-ssl-cert" fails to create the files (because the file is not executed) 
and  then the "chmod" and "chgrp" fail because there is no file to modify and 
exit with code 1.
you could either change the PATH envorinment variable for cron OR adapt the 
script so it doesn't fail (should have absolute paths anyway!!!)

it's two times in the postinstallation script [line 32 and line 40]

if the path gets changed to an absolute one, everything works as
expected (i tested this)

line 32 old:
make-ssl-cert generate-default-snakeoil --force-overwrite

line 32 new:
/usr/sbin/make-ssl-cert generate-default-snakeoil --force-overwrite

line 40 old:
make-ssl-cert generate-default-snakeoil

line 40 new:
/usr/sbin/make-ssl-cert generate-default-snakeoil


thats it ...! could be closed pretty easy and fast
also affects feisty version 1.0.13 --> same problem!
i haven't looked at the intrepid version of the postinst script, but i suspect 
the problem could be there too - worth a look ;)

-- 
package ssl-cert 1.0.14-0ubuntu2.1 failed to install/upgrade: 
https://bugs.launchpad.net/bugs/250400
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