I have a few tips to add to Debian specific installation page. Apparently there's no convenient way to submit a PR against GH wiki, so here we go...
diff --git a/Installation:-Debian-and-Ubuntu.md b/Installation:-Debian-and-Ubuntu.md
index c1136d0..0cb6b7d 100644
--- a/Installation:-Debian-and-Ubuntu.md
+++ b/Installation:-Debian-and-Ubuntu.md
@@ -35,6 +35,11 @@ gem install sup # sudo is not needed if not using system ruby
```
Note: On a freshly set-up Debian 8.1 with a virgin ruby installation, you might get an error while trying to install the latest version of Sup, which is thanks to a missing library (xapian). Easily fixed by fetching the native Debian version straight from the repository (`apt-get install ruby-xapian`) and running the above commands again ;)
+If you get `No such file or directory -- /usr/share/rubygems-integration/all/gems/rake-12.3.1/exe/rake`, installing fresh rake via rubygems (`gem install rake`) might help.
+
+If installation fails on `xapian-ruby` without any specific error message, try installing that package first (`gem install xapian-ruby`) and then sup.
+
+If you can't or don't want to install gems globally, there's always the option to install them under your home directory (`~/.gem/`) with `gem install --user-install <gemname>`. Then you need to also make sure you have gem binaries in your path. That you can achieve for example by appending `PATH="$HOME/.gem/ruby/2.5.0/bin:$PATH"` to your `~/.profile`.
### Rubygems `PATH` issue on old systems