diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2f019a1f8..100bc760d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,7 @@
 ## 0.6.0 (unreleased)
 
+  - SSH connection is retried 5 times if there is a connection refused.
+    Related to GH-140.
   - If `http_proxy` environmental variable is set, it will be used as the proxy
     box adding via http.
   - Remove `config.ssh.password`. It hasn't been used for a few versions
diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index c54466237..e83497aba 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -7,6 +7,8 @@ module Vagrant
   # replace the process with SSH itself, run a specific set of commands,
   # upload files, or even check if a host is up.
   class SSH
+    include Util::Retryable
+
     # Reference back up to the environment which this SSH object belongs
     # to
     attr_accessor :env
@@ -57,14 +59,16 @@ module Vagrant
       opts = opts.dup
       opts[:forward_agent] = true if env.config.ssh.forward_agent
 
-      Net::SSH.start(env.config.ssh.host,
-                     env.config.ssh.username,
-                     opts.merge( :port => port,
-                                 :keys => [env.config.ssh.private_key_path],
-                                 :user_known_hosts_file => [],
-                                 :paranoid => false,
-                                 :config => false)) do |ssh|
-        yield SSH::Session.new(ssh)
+      retryable(:tries => 5, :on => Errno::ECONNREFUSED) do
+        Net::SSH.start(env.config.ssh.host,
+                       env.config.ssh.username,
+                       opts.merge( :port => port,
+                                   :keys => [env.config.ssh.private_key_path],
+                                   :user_known_hosts_file => [],
+                                   :paranoid => false,
+                                   :config => false)) do |ssh|
+          yield SSH::Session.new(ssh)
+        end
       end
     end
 
@@ -72,16 +76,11 @@ module Vagrant
     # or StringIO, and `to` is expected to be a path. This method simply forwards
     # the arguments to `Net::SCP#upload!` so view that for more information.
     def upload!(from, to)
-      tries = 5
-
-      begin
+      retryable(:tries => 5, :on => IOError) do
         execute do |ssh|
           scp = Net::SCP.new(ssh.session)
           scp.upload!(from, to)
         end
-      rescue IOError
-        retry if (tries -= 1) > 0
-        raise
       end
     end
 
diff --git a/lib/vagrant/util.rb b/lib/vagrant/util.rb
index 83bb78662..bcfb27841 100644
--- a/lib/vagrant/util.rb
+++ b/lib/vagrant/util.rb
@@ -6,6 +6,7 @@ module Vagrant
     autoload :PlainLogger,               'vagrant/util/plain_logger'
     autoload :Platform,                  'vagrant/util/platform'
     autoload :ResourceLogger,            'vagrant/util/resource_logger'
+    autoload :Retryable,                 'vagrant/util/retryable'
     autoload :StackedProcRunner,         'vagrant/util/stacked_proc_runner'
     autoload :TemplateRenderer,          'vagrant/util/template_renderer'
   end
diff --git a/lib/vagrant/util/retryable.rb b/lib/vagrant/util/retryable.rb
new file mode 100644
index 000000000..2247cfe42
--- /dev/null
+++ b/lib/vagrant/util/retryable.rb
@@ -0,0 +1,22 @@
+module Vagrant
+  module Util
+    module Retryable
+      # Retries a given block a specified number of times in the
+      # event the specified exception is raised. If the retries
+      # run out, the final exception is raised.
+      #
+      # This code is adapted slightly from the following blog post:
+      # http://blog.codefront.net/2008/01/14/retrying-code-blocks-in-ruby-on-exceptions-whatever/
+      def retryable(opts=nil)
+        opts = { :tries => 1, :on => Exception }.merge(opts || {})
+
+        begin
+          return yield
+        rescue opts[:on]
+          retry if (opts[:tries] -= 1) > 0
+          raise
+        end
+      end
+    end
+  end
+end
diff --git a/test/vagrant/ssh_test.rb b/test/vagrant/ssh_test.rb
index e4106e122..55990dc0c 100644
--- a/test/vagrant/ssh_test.rb
+++ b/test/vagrant/ssh_test.rb
@@ -170,13 +170,6 @@ class SshTest < Test::Unit::TestCase
       @ssh.expects(:execute).yields(ssh).once
       @ssh.upload!("foo", "bar")
     end
-
-    should "retry 5 times" do
-      @ssh.expects(:execute).times(5).raises(IOError)
-      assert_raises(IOError) {
-        @ssh.upload!("foo", "bar")
-      }
-    end
   end
 
   context "checking if host is up" do
@@ -204,7 +197,7 @@ class SshTest < Test::Unit::TestCase
     end
 
     should "return false if the connection is refused" do
-      Net::SSH.expects(:start).raises(Errno::ECONNREFUSED)
+      Net::SSH.expects(:start).times(5).raises(Errno::ECONNREFUSED)
       assert_nothing_raised {
         assert !@ssh.up?
       }
diff --git a/test/vagrant/util/retryable_test.rb b/test/vagrant/util/retryable_test.rb
new file mode 100644
index 000000000..e8238b73e
--- /dev/null
+++ b/test/vagrant/util/retryable_test.rb
@@ -0,0 +1,38 @@
+require "test_helper"
+
+class RetryableUtilTest < Test::Unit::TestCase
+  setup do
+    @klass = Class.new do
+      extend Vagrant::Util::Retryable
+    end
+  end
+
+  should "retry specified number of times if exception is raised" do
+    proc = mock("proc")
+    proc.expects(:call).twice
+
+    assert_raises(RuntimeError) {
+      @klass.retryable(:tries => 2, :on => RuntimeError) do
+        proc.call
+        raise "An error"
+      end
+    }
+  end
+
+  should "only retry on specified exception" do
+    proc = mock("proc")
+    proc.expects(:call).once
+
+    assert_raises(StandardError) {
+      @klass.retryable(:tries => 5, :on => RuntimeError) do
+        proc.call
+        raise StandardError.new
+      end
+    }
+  end
+
+  should "return the value of the block" do
+    result = @klass.retryable { 7 }
+    assert_equal 7, result
+  end
+end