Deploying Rails to EC2 with Rubber - "Failed to connect to <ip>, retrying"

Question

I'm currently on Windows 8, attempting to deploy my Rails app to Amazon EC2 with Rubber following the Railscast #347 Rubber and Amazon EC2.

However, when trying to run cap rubber:create_staging, I get the following error when Rubber attempts to connect the Amazon EC2 instance:

** Failed to connect to <ip address>, retrying
* [32m2014-03-04 18:30:08 executing `rubber:_ensure_key_file_present´
* [32m2104-03-04 18:30:08 executing `rubber:_allow_root_ssh´
* [33mexecuting "sudo -p ´sudo password: ´  bash -l -c ´mkdir -p /root/.ssh &
& cp /home/ubuntu/.ssh/authorized_keys /root/.ssh/´"
  servers: ["<ip address"]

Every 15 attempts or so, it does this in between:

** timeout in initial connect, retrying
Trying to enable root login

And this just keeps on going, I let it try for 30 minutes to give the server time, so it's at least not about the server not-initializing.

Some suggestions I found on this were about the key_files, but I've checked those multiple times and am fairly certain they're correct. However, I am starting to doubt this is somehow related to windows. Could it be? The command it is trying to execute is for Linux, but I figured it's not for my computer, but the Amazon server its forwarding it to.

However, this is my first time deploying a Rails app and my knowledge about the subject is very limited, so I don't know about that. Thanks in advance to any help, it is hugely appreciated!

Here's my rubber.yml file.