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Here's what I've got so far:

# gem install passenger
Building native extensions.  This could take a while...
Successfully installed rack-1.2.1
Successfully installed passenger-2.2.15
2 gems installed
Installing ri documentation for rack-1.2.1...
Installing ri documentation for passenger-2.2.15...
Installing RDoc documentation for rack-1.2.1...
Installing RDoc documentation for passenger-2.2.15...

... but it's been stuck on "Installing RDoc documentation for passenger-2.2.15" for maybe 30 mins now. I'm a bit worried to kill it, since this could lead to a corrupt install.

Also, I've noticed that gem in general has been painfully slow compared to say, apt-get - is this normal?

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Hmm, weird, the SSH session just terminated. But I'm still connected to other sessions on that machine. Very very strange... – nbolton Jul 3 '10 at 11:09
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3 Answers

Gem is slow (at least compared to apt I've found). It will run faster if you don't generate the documentation: --no-ri --no-rdoc

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Thanks, I think that'll help! Documentation install is always so extremely slow, which sounds silly. – nbolton Jul 3 '10 at 12:00
That's because the documentation is generated from the RDoc comments in the .rb files. apt is only faster in this regard because it will just extract the documentation from the .deb archives. – joschi Jul 3 '10 at 12:25
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Re-running the command seems to have worked a 2nd time. But I'm still very worried that it just hung for 30 mins.

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Well if you dont use screen, that's alread a (just a simple, not huge) fail. You should use it always when you SSH into the machine.

(Sorry I just can't comment yet)

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Isn't screen installed and used on Debian Lenny by default? – nbolton Jul 3 '10 at 11:59
Screen is a handy tool in lots of cases, but not using it is hardly a "huge fail" – theotherreceive Jul 3 '10 at 12:03
Why not? If you have a stuck proccess, a stuck install, etc or you get a disconnect and you mess up.. that is not a fail? ... Well.. you are a strange admin, mate. – Shiki Jul 3 '10 at 12:06
@nbolton - It is installed. But you have to use it. First, fetch a simple config and put it to your ~/ folder with the .screenrc name. After that, look up a basic usage howto. And you are already a few steps forward. – Shiki Jul 3 '10 at 12:09
Cool thanks for the tip -- I thought it was on by default. – nbolton Jul 3 '10 at 12:14
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