diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index 8df293028..c68c93e40 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -18,7 +18,7 @@ module Vagrant
     # of options which override the configuration values.
     def connect(opts={})
       if Mario::Platform.windows?
-        error_and_exit(:ssh_unavailable_windows, 
+        error_and_exit(:ssh_unavailable_windows,
                        :key_path => env.config.ssh.private_key_path,
                        :ssh_port => port(opts))
       end
@@ -29,7 +29,14 @@ module Vagrant
       end
 
       check_key_permissions(options[:private_key_path])
-      Kernel.exec "ssh -p #{port(opts)} -o UserKnownHostsFile=/dev/null -o StrictHostKeyChecking=no -i #{options[:private_key_path]} #{options[:username]}@#{options[:host]}".strip
+
+      # Some hackery going on here. On Mac OS X Leopard (10.5), exec fails
+      # (GH-51). As a workaround, we fork and wait. On all other platforms,
+      # we simply exec.
+      pid = nil
+      pid = fork if Util::Platform.leopard?
+      Kernel.exec "ssh -p #{port(opts)} -o UserKnownHostsFile=/dev/null -o StrictHostKeyChecking=no -i #{options[:private_key_path]} #{options[:username]}@#{options[:host]}".strip if pid.nil?
+      Process.wait(pid) if pid
     end
 
     # Opens an SSH connection to this environment's virtual machine and yields
diff --git a/lib/vagrant/util/platform.rb b/lib/vagrant/util/platform.rb
new file mode 100644
index 000000000..80c4849c9
--- /dev/null
+++ b/lib/vagrant/util/platform.rb
@@ -0,0 +1,12 @@
+module Vagrant
+  module Util
+    # This class just contains some platform checking code.
+    class Platform
+      class <<self
+        def leopard?
+          RUBY_PLATFORM.downcase.include?("darwin9")
+        end
+      end
+    end
+  end
+end
\ No newline at end of file
diff --git a/test/vagrant/ssh_test.rb b/test/vagrant/ssh_test.rb
index 77c7d94b6..306c81cd4 100644
--- a/test/vagrant/ssh_test.rb
+++ b/test/vagrant/ssh_test.rb
@@ -15,6 +15,8 @@ class SshTest < Test::Unit::TestCase
       @ssh.stubs(:check_key_permissions)
       @ssh.stubs(:error_and_exit)
       Kernel.stubs(:exec)
+
+      Vagrant::Util::Platform.stubs(:leopard?).returns(false)
     end
 
     should "check key permissions prior to exec" do
@@ -38,7 +40,21 @@ class SshTest < Test::Unit::TestCase
       @ssh.connect(args)
     end
 
-    context "cheching windows" do
+    context "on leopard" do
+      setup do
+        Vagrant::Util::Platform.stubs(:leopard?).returns(true)
+      end
+
+      should "fork, exec, and wait" do
+        pid = mock("pid")
+        @ssh.expects(:fork).once.returns(pid)
+        Process.expects(:wait).with(pid)
+
+        @ssh.connect
+      end
+    end
+
+    context "checking windows" do
       should "error and exit if the platform is windows" do
         Mario::Platform.expects(:windows?).returns(true)
         @ssh.expects(:error_and_exit).with do |error_name, opts|