I recently deployed Octopress on a new cloud server. For the most part, the Octopress documentation was accurate, with no major hiccups; however, the vanilla Debian 7.0 base install is missing a couple packages to clear a zlib error you may come across. Fine with me, as I prefer a lean install base anyways.
During the Octopress install you may come across this:
1 2 3 4 5
1 2 3
That should do it.