Never followed up on this... I'm 99% sure that this was flaky hardware on my end.
** Changed in: dpkg (Ubuntu) Status: New => Invalid -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/507538 Title: package openssl 0.9.8g-16ubuntu3.1 failed to install/upgrade: unable to create `/usr/share/doc/openssl/README.gz.dpkg-new' (while processing `./usr/share/doc/openssl/README.gz'): Invalid argument -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs