diff --git a/lib/hobo/vm.rb b/lib/hobo/vm.rb
index 484012985..7b0a264ef 100644
--- a/lib/hobo/vm.rb
+++ b/lib/hobo/vm.rb
@@ -174,13 +174,14 @@ error
       logger.info "Waiting for VM to boot..."
 
       Hobo.config[:ssh][:max_tries].to_i.times do |i|
-        sleep 5 unless ENV['HOBO_ENV'] == 'test'
         logger.info "Trying to connect (attempt ##{i+1} of #{Hobo.config[:ssh][:max_tries]})..."
 
         if Hobo::SSH.up?
           logger.info "VM booted and ready for use!"
           return true
         end
+
+        sleep 5 unless ENV['HOBO_ENV'] == 'test'
       end
 
       logger.info "Failed to connect to VM! Failed to boot?"
diff --git a/test/hobo/vm_test.rb b/test/hobo/vm_test.rb
index 4acfb8fe1..ab0984d37 100644
--- a/test/hobo/vm_test.rb
+++ b/test/hobo/vm_test.rb
@@ -113,6 +113,7 @@ class VMTest < Test::Unit::TestCase
 
       should "start the VM in headless mode" do
         @mock_vm.expects(:start).with(:headless, true).once
+        Hobo::SSH.expects(:up?).once.returns(true)
         @vm.start
       end