diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index 61458aed9..3a5f24487 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -57,9 +57,16 @@ 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)
-      execute do |ssh|
-        scp = Net::SCP.new(ssh.session)
-        scp.upload!(from, to)
+      tries = 5
+
+      begin
+        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/test/vagrant/ssh_test.rb b/test/vagrant/ssh_test.rb
index a13b4ed60..802515679 100644
--- a/test/vagrant/ssh_test.rb
+++ b/test/vagrant/ssh_test.rb
@@ -144,6 +144,13 @@ 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