I think this is just a verbose output from the -d . Does the server really start (after creating the output load)?
What's happening? Using -d , set the Rubys $DEBUG flag to true . Then Rack tries to download the application through config.ru , which in turn downloads your app.rb The first thing in app.rb is require 'sinatra' .
Rubygems replaces the original require method with its own. When you call require , it tries to download the file, usually using the existing download path and the original require method . If the gem has not been loaded, it will raise a LoadError that Rubygems catches before loading the gem.
With the $DEBUG flag set, Ruby throws a message when an exception occurs, even if it is saved and processed, and this is what you see.
To avoid this, simply lower the -d flag to your call to rackup (perhaps turning on warnings with -w will give you a fairly detailed output without dropping you too much).
If the server does not start, it will be another problem, not a Sinatra search. If so, you need to check the rest of the output for clues.
(Note that I initially thought something else was happening, and that is what my questions were in his comments about.)
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