diff --git a/CHANGELOG.md b/CHANGELOG.md
index b9b957af8..a751e3e8a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,7 @@
     logging is silent.
   - Linux uses `shutdown -h` instead of `halt` to hopefully more consistently
     power off the system. [GH-575]
+  - Tweaks to SSH to hopefully be more reliable in coming up.
 
 ## 0.8.8 (December 1, 2011)
 
diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index fea33ad5d..42d4f27aa 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -74,6 +74,8 @@ module Vagrant
 
       # Connect to SSH and gather the session
       session = retryable(:tries => @vm.config.ssh.max_tries, :on => exceptions) do
+        sleep 4 # Hacky but helps with issue #391, #455, etc.
+
         connection = Net::SSH.start(@vm.config.ssh.host,
                                     @vm.config.ssh.username,
                                     opts.merge( :keys => [private_key_path],
@@ -81,6 +83,8 @@ module Vagrant
                                                 :user_known_hosts_file => [],
                                                 :paranoid => false,
                                                 :config => false))
+
+        sleep 4 # Hacky but helps with issue #391, #455, etc.
         SSH::Session.new(connection, @vm)
       end