diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
new file mode 100644
index 000000000..e01941b84
--- /dev/null
+++ b/lib/vagrant/ssh.rb
@@ -0,0 +1,132 @@
+require 'log4r'
+
+require 'vagrant/util/file_util'
+require 'vagrant/util/file_mode'
+require 'vagrant/util/platform'
+require 'vagrant/util/safe_exec'
+
+module Vagrant
+  # Manages SSH connection information as well as allows opening an
+  # SSH connection.
+  class SSH
+    include Util::SafeExec
+
+    def initialize(vm)
+      @vm     = vm
+      @logger = Log4r::Logger.new("vagrant::ssh")
+    end
+
+    # Returns a hash of information necessary for accessing this
+    # virtual machine via SSH.
+    #
+    # @return [Hash]
+    def info
+      results = {
+        :host          => @vm.config.ssh.host,
+        :port          => @vm.config.ssh.port || @vm.driver.ssh_port(@vm.config.ssh.guest_port),
+        :username      => @vm.config.ssh.username,
+        :forward_agent => @vm.config.ssh.forward_agent,
+        :forward_x11   => @vm.config.ssh.forward_x11
+      }
+
+      # This can happen if no port is set and for some reason Vagrant
+      # can't detect an SSH port.
+      raise Errors::SSHPortNotDetected if !results[:port]
+
+      # Determine the private key path, which is either set by the
+      # configuration or uses just the built-in insecure key.
+      pk_path = @vm.config.ssh.private_key_path || @vm.env.default_private_key_path
+      results[:private_key_path] = File.expand_path(pk_path, @vm.env.root_path)
+
+      # We need to check and fix the private key permissions
+      # to make sure that SSH gets a key with 0600 perms.
+      check_key_permissions(results[:private_key_path])
+
+      # Return the results
+      return results
+    end
+
+    # Connects to the environment's virtual machine, replacing the ruby
+    # process with an SSH process.
+    #
+    # @param [Hash] opts Options hash
+    # @options opts [Boolean] :plain_mode If True, doesn't authenticate with
+    #   the machine, only connects, allowing the user to connect.
+    def exec(opts={})
+      # Get the SSH information and cache it here
+      ssh_info = info
+
+      # Ensure the platform supports ssh. On Windows there are several programs which
+      # include ssh, notably git, mingw and cygwin, but make sure ssh is in the path!
+      if !Util::FileUtil.which("ssh")
+        if Util::Platform.windows?
+          raise Errors::SSHUnavailableWindows, :host => ssh_info[:host],
+                                               :port => ssh_info[:port],
+                                               :username => ssh_info[:username],
+                                               :key_path => ssh_info[:private_key_path]
+        end
+        raise Errors::SSHUnavailable 
+      end
+
+      # If plain mode is enabled then we don't do any authentication (we don't
+      # set a user or an identity file)
+      plain_mode = opts[:plain_mode]
+
+      options = {}
+      options[:host] = ssh_info[:host]
+      options[:port] = ssh_info[:port]
+      options[:username] = ssh_info[:username]
+      options[:private_key_path] = ssh_info[:private_key_path]
+
+      # Command line options
+      command_options = ["-p", options[:port].to_s, "-o", "UserKnownHostsFile=/dev/null",
+                         "-o", "StrictHostKeyChecking=no", "-o", "LogLevel=QUIET"]
+
+      # Solaris/OpenSolaris/Illumos uses SunSSH which doesn't support the IdentitiesOnly option
+      # (Also don't use it in plain mode, it'll skip user agents.)
+      command_options += ["-o", "IdentitiesOnly=yes"] if !(Util::Platform.solaris? || plain_mode)
+
+      command_options += ["-i", options[:private_key_path]] if !plain_mode
+      command_options += ["-o", "ForwardAgent=yes"] if ssh_info[:forward_agent]
+
+      # If there are extra options, then we append those
+      command_options.concat(opts[:extra_args]) if opts[:extra_args]
+
+      if ssh_info[:forward_x11]
+        # Both are required so that no warnings are shown regarding X11
+        command_options += ["-o", "ForwardX11=yes"]
+        command_options += ["-o", "ForwardX11Trusted=yes"]
+      end
+
+      host_string = options[:host]
+      host_string = "#{options[:username]}@#{host_string}" if !plain_mode
+      command_options << host_string
+      @logger.info("Invoking SSH: #{command_options.inspect}")
+      safe_exec("ssh", *command_options)
+    end
+
+    # Checks the file permissions for a private key, resetting them
+    # if needed.
+    def check_key_permissions(key_path)
+      # Windows systems don't have this issue
+      return if Util::Platform.windows?
+
+      @logger.debug("Checking key permissions: #{key_path}")
+      stat = File.stat(key_path)
+
+      if stat.owned? && Util::FileMode.from_octal(stat.mode) != "600"
+        @logger.info("Attempting to correct key permissions to 0600")
+        File.chmod(0600, key_path)
+
+        stat = File.stat(key_path)
+        if Util::FileMode.from_octal(stat.mode) != "600"
+          raise Errors::SSHKeyBadPermissions, :key_path => key_path
+        end
+      end
+    rescue Errno::EPERM
+      # This shouldn't happen since we verified we own the file, but
+      # it is possible in theory, so we raise an error.
+      raise Errors::SSHKeyBadPermissions, :key_path => key_path
+    end
+  end
+end
diff --git a/lib/vagrant/util/file_util.rb b/lib/vagrant/util/file_util.rb
new file mode 100644
index 000000000..4bada368b
--- /dev/null
+++ b/lib/vagrant/util/file_util.rb
@@ -0,0 +1,36 @@
+module Vagrant
+  module Util
+    class FileUtil
+      # Cross-platform way of finding an executable in the $PATH.
+      #
+      #   which('ruby') #=> /usr/bin/ruby
+      #   by http://stackoverflow.com/users/11687/mislav
+      #
+      # This code is adapted from the following post by mislav:
+      #   http://stackoverflow.com/questions/2108727/which-in-ruby-checking-if-program-exists-in-path-from-ruby
+      def self.which(cmd)
+
+        # If the PATHEXT variable is empty, we're on *nix and need to find the exact filename
+        exts = nil
+        if !Util::Platform.windows? || ENV['PATHEXT'].nil?
+          exts = ['']
+        # On Windows: if filename contains an extension, we must match that exact filename
+        elsif File.extname(cmd).length != 0
+          exts = ['']
+        # On Windows: otherwise try to match all possible executable file extensions (.EXE .COM .BAT etc.)
+        else
+          exts = ENV['PATHEXT'].split(';')
+        end
+
+        ENV['PATH'].split(File::PATH_SEPARATOR).each do |path|
+          exts.each do |ext|
+            exe = "#{path}#{File::SEPARATOR}#{cmd}#{ext}"
+            return exe if File.executable? exe
+          end
+        end
+        
+        return nil
+      end
+    end
+  end
+end
diff --git a/lib/vagrant/util/ssh.rb b/lib/vagrant/util/ssh.rb
index 7b73308c4..fa211e3f3 100644
--- a/lib/vagrant/util/ssh.rb
+++ b/lib/vagrant/util/ssh.rb
@@ -1,5 +1,6 @@
 require "log4r"
 
+require "vagrant/util/file_util"
 require "vagrant/util/file_mode"
 require "vagrant/util/platform"
 require "vagrant/util/safe_exec"
@@ -52,20 +53,19 @@ module Vagrant
       # @param [Hash] opts These are additional options that are supported
       #   by exec.
       def self.exec(ssh_info, opts={})
-        # If we're running Windows, raise an exception since we currently
-        # still don't support exec-ing into SSH. In the future this should
-        # certainly be possible if we can detect we're in an environment that
-        # supports it.
-        if Platform.windows?
-          raise Errors::SSHUnavailableWindows,
-            :host => ssh_info[:host],
-            :port => ssh_info[:port],
-            :username => ssh_info[:username],
-            :key_path => ssh_info[:private_key_path]
-        end
+        # Ensure the platform supports ssh. On Windows there are several programs which
+        # include ssh, notably git, mingw and cygwin, but make sure ssh is in the path!
+        if !FileUtil.which("ssh")
+          if Platform.windows?
+            raise Errors::SSHUnavailableWindows,
+              :host => ssh_info[:host],
+              :port => ssh_info[:port],
+              :username => ssh_info[:username],
+              :key_path => ssh_info[:private_key_path]
+          end
 
-        # Verify that we have SSH available on the system.
-        raise Errors::SSHUnavailable if !Kernel.system("which ssh > /dev/null 2>&1")
+          raise Errors::SSHUnavailable
+        end
 
         # If plain mode is enabled then we don't do any authentication (we don't
         # set a user or an identity file)
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 1950215b2..03c1af035 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -298,9 +298,10 @@ en:
         guest port value, or specify an explicit SSH port with `config.ssh.port`.
       ssh_unavailable: "`ssh` binary could not be found. Is an SSH client installed?"
       ssh_unavailable_windows: |-
-        `vagrant ssh` isn't available on the Windows platform. You are still able
-        to SSH into the virtual machine if you get a Windows SSH client (such as
-        PuTTY). The authentication information is shown below:
+        `ssh` executable not found in any directories in the %PATH% variable. Is an
+        SSH client installed? Try installing Cygwin, MinGW or Git, all of which
+        contain an SSH client. Or use the PuTTY SSH client with the following
+        authentication information shown below:
 
         Host: %{host}
         Port: %{port}
diff --git a/test/unit/vagrant/util/file_util_test.rb b/test/unit/vagrant/util/file_util_test.rb
new file mode 100644
index 000000000..61d7897af
--- /dev/null
+++ b/test/unit/vagrant/util/file_util_test.rb
@@ -0,0 +1,46 @@
+require File.expand_path("../../../base", __FILE__)
+
+require 'vagrant/util/file_util'
+require 'vagrant/util/platform'
+
+describe Vagrant::Util::FileUtil do
+
+  def tester (file_extension, test_extension, mode, &block)
+    # create file in temp directory
+    filename = '__vagrant_unit_test__'
+    dir = Dir.tmpdir
+    file = Pathname(dir) + (filename + file_extension)
+    file.open("w") { |f| f.write("#") }
+    file.chmod(mode)
+
+    # set the path to the directory where the file is located
+    savepath = ENV['PATH']
+    ENV['PATH'] = dir.to_s
+    block.call filename + test_extension
+    ENV['PATH'] = savepath
+
+    file.unlink
+  end
+
+  it "should return a path for an executable file" do
+    tester '.bat', '.bat', 0755 do |name|
+      Vagrant::Util::FileUtil.which(name).should_not be_nil
+    end
+  end
+
+  if Vagrant::Util::Platform.windows?
+    it "should return a path for a Windows executable file" do
+      tester '.bat', '', 0755 do |name|
+        Vagrant::Util::FileUtil.which(name).should_not be_nil
+      end
+    end
+  end
+
+  it "should return nil for a non-executable file" do
+    tester '.txt', '.txt', 0644 do |name|
+      Vagrant::Util::FileUtil.which(name).should be_nil
+    end
+  end
+
+end
+