Why won't Vagrant ssh into my virtual box when I use `Vagrant Up` on Windows 7 command line?

During Vagrant Up your Windows system tries to connect to SSH. If you type on your command line:

set VAGRANT_LOG=INFO

You may see it fail and try a couple of times. It looks like this:

INFO ssh: Connecting to SSH: 127.0.0.1:2222

This is happening because the timeout is set to 10. This can be modified by placing the following in your Vagrantfile:

config.ssh.timeout = 300

You can use any number you like but I recommend something above 100.

Sources:

  1. This guy had some useful troubleshooting information.
  2. Vagrant Docs for Vagrantfiles
  3. Vagrant Docs for Vagrantfile SSH Timeout
  4. Vagrant Docs for Debugging
  5. Hours of Troubleshooting (Keep Smilin')