Ryan C. wrote in post #990276:
> I have tried editing my gem paths, but that shouldn't be it since
> sinatra works, right?

How did you install sinatra? You might be using the native Debian 
package rather than the gem:

$ apt-cache search sinatra
libsinatra-ruby - Ruby web-development dressed in a DSL (Ruby 1.8 
package)
libsinatra-ruby-doc - Ruby web-development dressed in a DSL 
(documentation)
libsinatra-ruby1.8 - Ruby web-development dressed in a DSL
libsinatra-ruby1.9.1 - Ruby web-development dressed in a DSL

in which case the gems dir may not in fact be on your search path.

I suggest you try the following:

export PATH=/var/lib/gems/1.8/bin:$PATH
shotgun ...blah blah...

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