diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index 4b8a1e22c..629b6570d 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -95,7 +95,7 @@ module Vagrant
         exceptions = [Errno::ECONNREFUSED, Net::SSH::Disconnect]
 
         # Connect to SSH and gather the session
-        session = retryable(:tries => 5, :on => exceptions) do
+        session = retryable(:tries => env.config.ssh.max_tries, :on => exceptions) do
           connection = Net::SSH.start(env.config.ssh.host,
                          env.config.ssh.username,
                          opts.merge( :keys => [env.config.ssh.private_key_path],
diff --git a/lib/vagrant/ssh/session.rb b/lib/vagrant/ssh/session.rb
index fe80192c7..d68862a1e 100644
--- a/lib/vagrant/ssh/session.rb
+++ b/lib/vagrant/ssh/session.rb
@@ -61,7 +61,7 @@ module Vagrant
       # the actual `exec!` implementation, except that this
       # implementation also reports `:exit_status` to the block if given.
       def exec!(commands, options=nil, &block)
-        retryable(:tries => 5, :on => [IOError, Net::SSH::Disconnect], :sleep => 1.0) do
+        retryable(:tries => env.config.ssh.max_tries, :on => [IOError, Net::SSH::Disconnect], :sleep => 1.0) do
           metach = session.open_channel do |ch|
             ch.exec("#{env.config.ssh.shell} -l") do |ch2, success|
               # Set the terminal