SS, I'm still concerned about a fingerprinting attack on this software. It tries to install the following gems from rubygems.org: awesome_print gtk2 mechanize nokogiri socksify vrlib I also see it fetching these: pkg-config glib2 atk cairo net-http-digest_auth net-http-persistent mime-types ntlm-http webrobots unf_ext unf domain_name require_all If this is the only software in the world that downloads this specific combo of gems, then an attacker with access to the rubygems.org server logs can enumerate the users of this software. Installation on Tails should be fine, because all connections are transparently proxied over Tor. On other Linux distros, you could include instructions to run the make command with torsocks, which should be installed if the headless Tor client is installed. On Windows, I'm not sure what to do. Is there a Windows version of torsocks that can be bundled with it? Edit: I found these, but haven't tried them... http://www.freehaven.net/~aphex/torcap/ https://github.com/cpatulea/TorCap2