Okay I found it out by myself, here's the working code if someone else 
ever wants to do this:
http://pastie.caboo.se/67910

The problem was that Ruby already uses a timeout for the Net::HTTP class 
and because of this, you can't wrap another timeout around it. But you 
can set the timeout Ruby uses with http.read_timeout and 
http.open_timeout. This way I was able to handle the Timeout::Error and 
now everything works just fine.

Chris Colon wrote:
> Hi,
> I'm trying to download a file with Ruby from a website. Everything works
> fine, but I can't get Ruby to retry the download when for example the
> internet connection breaks during the download.
> 
> Here's my code so far (it's easier to read in a pastie):
> http://pastie.caboo.se/67574
> 
> The Timeout::Error exception never happens, even though it should time
> out after 5 seconds. The funny thing is, if I deactivate my internet and
> then reconnect it, it does continue the download of the file, even
> though the commands under "rescue Timeout::Error" aren't executed.
> 
> I hope someone can help me, I googled for an hour and tried tons of
> different things that I found in the API docs, but I'm pretty stuck
> right now.


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