Finally resolved by downloading the .deb and:

$ sudo dpgk -i --force-all openssl_0.9.8g-16ubuntu3.1_i386.deb

-- 
package openssl 0.9.8g-16ubuntu3.1 failed to install/upgrade: failed in 
buffer_read(fd): md5hash
https://bugs.launchpad.net/bugs/557641
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