Windows Server 2008 vagrant box running but unable to add remote Ruby SDK in RubyMine

I'm running RubyMine on macOS High Sierra 0.13.3 (17D47), and I have a Windows Server 2008 R2 SP1 Vagrant box which is running that I can SSH into (Microsoft's implementation of OpenSSH) fine.  I'm not using keys.

When I try to add the Remote Ruby SDK location in RubyMine is gives me an SFTP error.  Or, if I try to change the Ruby bin path it gives me an error.  On Windows, my Ruby bin path is C:\Ruby21-x64\bin not /usr/ruby/bin.  Here's the error:

Vagrant file:


Vagrant.configure("2") do |config| = 'windows-server-2008-r2-sp1'
config.vm.guest = :windows
config.winrm.timeout = 500
config.ssh.username = 'vagrant'
config.ssh.password = 'vagrant'
config.ssh.insert_key = false :forwarded_port, guest: 80, host: 8080 :forwarded_port, guest: 5985, host: 5985 :forwarded_port, guest: 1433, host: 1433 "private_network", ip: ""
config.vm.provider "virtualbox" do |vb|
vb.gui = true

vagrant ssh-config:

Host default
User vagrant
  Port 2222
  UserKnownHostsFile /dev/null
  StrictHostKeyChecking no
  PasswordAuthentication no
IdentitiesOnly yes
LogLevel FATAL






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Hello Edward,

sorry for the delay. Unfortunately I didn't manage to reproduce the problem with your Vagrantfile since the box wasn't found, is it public?

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Hi Olga, it's a Windows Server 2008 R2 SP1 vagrant box which probably isn't available for free publicly.  I used my company's MSDN subscription to obtain the original iso for Windows Server 2008 R2 SP1, and manually installed it into a VirtualBox VM, then converted it to Vagrant, etc.

In any case, I believe the root issue is that RubyMine doesn't honor the key-less SSH login, and it's also looking for Ruby in the wrong place on Windows.


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