diff --git a/internal/core/machine.go b/internal/core/machine.go
index 9bac5d04a..f4f4bba30 100644
--- a/internal/core/machine.go
+++ b/internal/core/machine.go
@@ -98,6 +98,17 @@ func (m *Machine) Box() (b core.Box, err error) {
 
 // Guest implements core.Machine
 func (m *Machine) Guest() (g core.Guest, err error) {
+	comm, err := m.Communicate()
+	if err != nil {
+		return nil, err
+	}
+	isReady, err := comm.Ready(m)
+	if err != nil {
+		return nil, err
+	}
+	if !isReady {
+		return nil, fmt.Errorf("unable to communicate with guest")
+	}
 	defer func() {
 		if g != nil {
 			err = seedPlugin(g, m)
diff --git a/lib/vagrant/machine/remote.rb b/lib/vagrant/machine/remote.rb
index 60014db88..225c96589 100644
--- a/lib/vagrant/machine/remote.rb
+++ b/lib/vagrant/machine/remote.rb
@@ -85,7 +85,6 @@ module Vagrant
       end
 
       def guest
-        # require "pry-remote"; binding.pry_remote
         raise Errors::MachineGuestNotReady if !communicate.ready?
         if !@guest
           @guest = Guest.new(self, nil, nil)
diff --git a/plugins/commands/serve/client/target/machine.rb b/plugins/commands/serve/client/target/machine.rb
index 3551835f9..a64f7ec0f 100644
--- a/plugins/commands/serve/client/target/machine.rb
+++ b/plugins/commands/serve/client/target/machine.rb
@@ -37,7 +37,6 @@ module VagrantPlugins
           end
 
           # @return [Guest] machine guest
-          # TODO: This needs to be loaded properly
           def guest
             g = client.guest(Empty.new)
             Guest.load(g, broker: broker)