diff --git a/CHANGELOG.md b/CHANGELOG.md
index cc454761c..82a3c90a8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,7 @@
   - Chef provisioners no longer depend on a "v-root" share being
     available. [GH-556]
   - NFS should work for FreeBSD hosts now. [GH-510]
+  - SSH executed methods respect `config.ssh.max_tries`. [GH-508]
 
 ## 0.8.7 (September 13, 2011)
 
diff --git a/test/unit/vagrant/ssh/session_test.rb b/test/unit/vagrant/ssh/session_test.rb
index 8c6880e41..06b1e7d12 100644
--- a/test/unit/vagrant/ssh/session_test.rb
+++ b/test/unit/vagrant/ssh/session_test.rb
@@ -10,8 +10,8 @@ class SshSessionTest < Test::Unit::TestCase
   end
 
   context "exec!" do
-    should "retry 5 times" do
-      @session.expects(:open_channel).times(5).raises(IOError)
+    should "retry max_tries times" do
+      @session.expects(:open_channel).times(@env.config.ssh.max_tries).raises(IOError)
       assert_raises(IOError) {
         @instance.exec!("foo")
       }
diff --git a/test/unit/vagrant/ssh_test.rb b/test/unit/vagrant/ssh_test.rb
index 61e02178f..38131b480 100644
--- a/test/unit/vagrant/ssh_test.rb
+++ b/test/unit/vagrant/ssh_test.rb
@@ -197,7 +197,7 @@ class SshTest < Test::Unit::TestCase
     end
 
     should "return false if the connection is refused" do
-      Net::SSH.expects(:start).times(5).raises(Errno::ECONNREFUSED)
+      Net::SSH.expects(:start).times(@env.config.ssh.max_tries).raises(Errno::ECONNREFUSED)
       assert_nothing_raised {
         assert !@ssh.up?
       }