diff --git a/config/default.rb b/config/default.rb
index 95cc6ab6c..c5476792d 100644
--- a/config/default.rb
+++ b/config/default.rb
@@ -5,8 +5,7 @@ Vagrant.configure("2") do |config|
   config.ssh.forward_x11 = false
   config.ssh.guest_port = 22
   config.ssh.keep_alive = true
-  config.ssh.max_tries = 100
-  config.ssh.timeout = 30
+  config.ssh.timeout = 300
   config.ssh.shell = "bash -l"
 
   config.ssh.default.username = "vagrant"
diff --git a/lib/vagrant/action.rb b/lib/vagrant/action.rb
index 67e71decc..52164b462 100644
--- a/lib/vagrant/action.rb
+++ b/lib/vagrant/action.rb
@@ -24,6 +24,7 @@ module Vagrant
       autoload :SetHostname, "vagrant/action/builtin/set_hostname"
       autoload :SSHExec, "vagrant/action/builtin/ssh_exec"
       autoload :SSHRun,  "vagrant/action/builtin/ssh_run"
+      autoload :WaitForCommunicator, "vagrant/action/builtin/wait_for_communicator"
     end
 
     module General
diff --git a/lib/vagrant/action/builtin/mixin_provisioners.rb b/lib/vagrant/action/builtin/mixin_provisioners.rb
index aa303cb08..ff82619ca 100644
--- a/lib/vagrant/action/builtin/mixin_provisioners.rb
+++ b/lib/vagrant/action/builtin/mixin_provisioners.rb
@@ -13,10 +13,10 @@ module Vagrant
           @_provisioner_types = {}
 
           # Get all the configured provisioners
-          @_provisioner_instances = env[:machine].config.vm.provisioners.map do |provisioner|
+          @_provisioner_instances = @env[:machine].config.vm.provisioners.map do |provisioner|
             # Instantiate the provisioner
             klass  = Vagrant.plugin("2").manager.provisioners[provisioner.name]
-            result = klass.new(env[:machine], provisioner.config)
+            result = klass.new(@env[:machine], provisioner.config)
 
             # Store in the type map so that --provision-with works properly
             @_provisioner_types[result] = provisioner.name
diff --git a/lib/vagrant/action/builtin/provision.rb b/lib/vagrant/action/builtin/provision.rb
index 8e4838cbb..dbb8f5dc1 100644
--- a/lib/vagrant/action/builtin/provision.rb
+++ b/lib/vagrant/action/builtin/provision.rb
@@ -20,6 +20,8 @@ module Vagrant
         end
 
         def call(env)
+          @env = env
+
           # Check if we're even provisioning things.
           enabled = true
           enabled = env[:provision_enabled] if env.has_key?(:provision_enabled)
diff --git a/lib/vagrant/action/builtin/provisioner_cleanup.rb b/lib/vagrant/action/builtin/provisioner_cleanup.rb
index bebfbe11f..3d826291a 100644
--- a/lib/vagrant/action/builtin/provisioner_cleanup.rb
+++ b/lib/vagrant/action/builtin/provisioner_cleanup.rb
@@ -1,19 +1,25 @@
 require "log4r"
 
+require_relative "mixin_provisioners"
+
 module Vagrant
   module Action
     module Builtin
       # This action will run the cleanup methods on provisioners and should
       # be used as part of any Destroy action.
       class ProvisionerCleanup
+        include MixinProvisioners
+
         def initialize(app, env)
           @app    = app
           @logger = Log4r::Logger.new("vagrant::action::builtin::provision_cleanup")
         end
 
         def call(env)
+          @env = env
+
           # Ask the provisioners to modify the configuration if needed
-          provisioners.each do |p|
+          provisioner_instances.each do |p|
             env[:ui].info(I18n.t(
               "vagrant.provisioner_cleanup",
               name: provisioner_type_map[p].to_s))
diff --git a/lib/vagrant/action/builtin/wait_for_communicator.rb b/lib/vagrant/action/builtin/wait_for_communicator.rb
new file mode 100644
index 000000000..462a39b1b
--- /dev/null
+++ b/lib/vagrant/action/builtin/wait_for_communicator.rb
@@ -0,0 +1,76 @@
+module Vagrant
+  module Action
+    module Builtin
+      # This waits for the communicator to be ready for a set amount of
+      # time.
+      class WaitForCommunicator
+        def initialize(app, env, states=nil)
+          @app    = app
+          @states = states
+        end
+
+        def call(env)
+          # Wait for ready in a thread so that we can continually check
+          # for interrupts.
+          ready_thr = Thread.new do
+            Thread.current[:result] = env[:machine].communicate.wait_for_ready(
+              env[:machine].config.ssh.timeout)
+          end
+
+          # Start a thread that verifies the VM stays in a good state.
+          states_thr = Thread.new do
+            Thread.current[:result] = true
+
+            # If we aren't caring about states, just basically put this
+            # thread to sleep because it'll get killed later.
+            if !@states
+              while true
+                sleep 300
+              end
+
+              next
+            end
+
+            # Otherwise, periodically verify the VM isn't in a bad state.
+            while true
+              state = env[:machine].provider.state.id
+              if !@states.include?(state)
+                Thread.current[:result] = false
+                break
+              end
+            end
+          end
+
+          # Wait for a result or an interrupt
+          env[:ui].info I18n.t("vagrant.boot_waiting")
+          while ready_thr.alive? && states_thr.alive?
+            return if env[:interrupted]
+          end
+
+          # If it went into a bad state, then raise an error
+          if !states_thr[:result]
+            raise Errors::VMBootBadState,
+              valid: @states.join(", "),
+              invalid: env[:machine].provider.state.id
+          end
+
+          # If it didn't boot, raise an error
+          if !ready_thr[:result]
+            raise Errors::VMBootTimeout
+          end
+
+          env[:ui].info I18n.t("vagrant.boot_completed")
+
+          # Make sure our threads are all killed
+          ready_thr.kill
+          states_thr.kill
+
+          @app.call(env)
+        ensure
+          ready_thr.kill
+          states_thr.kill
+        end
+      end
+    end
+  end
+end
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 41f4a8890..05898297a 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -543,6 +543,14 @@ module Vagrant
       error_key(:no_base_mac, "vagrant.actions.vm.match_mac")
     end
 
+    class VMBootBadState < VagrantError
+      error_key(:boot_bad_state)
+    end
+
+    class VMBootTimeout < VagrantError
+      error_key(:boot_timeout)
+    end
+
     class VMCustomizationFailed < VagrantError
       error_key(:failure, "vagrant.actions.vm.customize")
     end
diff --git a/lib/vagrant/plugin/v2/communicator.rb b/lib/vagrant/plugin/v2/communicator.rb
index 97c84d4d4..2f4d0b590 100644
--- a/lib/vagrant/plugin/v2/communicator.rb
+++ b/lib/vagrant/plugin/v2/communicator.rb
@@ -1,3 +1,5 @@
+require "timeout"
+
 module Vagrant
   module Plugin
     module V2
@@ -44,6 +46,25 @@ module Vagrant
           false
         end
 
+        # wait_for_ready waits until the communicator is ready, blocking
+        # until then. It will wait up to the given duration or raise an
+        # exception if something goes wrong.
+        def wait_for_ready(duration)
+          # By default, we implement a naive solution.
+          begin
+            Timeout.timeout(duration) do
+              while true
+                return true if ready?
+                sleep 0.2
+              end
+            end
+          rescue Timeout::Error
+            # We timed out, we failed.
+          end
+
+          return false
+        end
+
         # Download a file from the remote machine to the local machine.
         #
         # @param [String] from Path of the file on the remote machine.
diff --git a/plugins/kernel_v2/config/ssh.rb b/plugins/kernel_v2/config/ssh.rb
index 6ed8ff5ff..d6d5cdd84 100644
--- a/plugins/kernel_v2/config/ssh.rb
+++ b/plugins/kernel_v2/config/ssh.rb
@@ -9,7 +9,6 @@ module VagrantPlugins
       attr_accessor :forward_x11
       attr_accessor :guest_port
       attr_accessor :keep_alive
-      attr_accessor :max_tries
       attr_accessor :shell
       attr_accessor :timeout
 
@@ -22,7 +21,6 @@ module VagrantPlugins
         @forward_x11      = UNSET_VALUE
         @guest_port = UNSET_VALUE
         @keep_alive = UNSET_VALUE
-        @max_tries  = UNSET_VALUE
         @shell      = UNSET_VALUE
         @timeout    = UNSET_VALUE
 
@@ -43,7 +41,6 @@ module VagrantPlugins
         @forward_x11   = false if @forward_x11 == UNSET_VALUE
         @guest_port = nil if @guest_port == UNSET_VALUE
         @keep_alive = false if @keep_alive == UNSET_VALUE
-        @max_tries  = nil if @max_tries == UNSET_VALUE
         @shell      = nil if @shell == UNSET_VALUE
         @timeout    = nil if @timeout == UNSET_VALUE
 
@@ -57,7 +54,7 @@ module VagrantPlugins
       def validate(machine)
         errors = super
 
-        [:max_tries, :timeout].each do |field|
+        [:timeout].each do |field|
           value = instance_variable_get("@#{field}".to_sym)
           errors << I18n.t("vagrant.config.common.error_empty", :field => field) if !value
         end
diff --git a/plugins/providers/virtualbox/action.rb b/plugins/providers/virtualbox/action.rb
index 5608d8a23..eb03dd8ee 100644
--- a/plugins/providers/virtualbox/action.rb
+++ b/plugins/providers/virtualbox/action.rb
@@ -71,6 +71,7 @@ module VagrantPlugins
           b.use SaneDefaults
           b.use Customize, "pre-boot"
           b.use Boot
+          b.use WaitForCommunicator, [:starting, :running]
           b.use Customize, "post-boot"
           b.use CheckGuestAdditions
         end
diff --git a/plugins/providers/virtualbox/action/boot.rb b/plugins/providers/virtualbox/action/boot.rb
index 58b3a8b4b..589a49d69 100644
--- a/plugins/providers/virtualbox/action/boot.rb
+++ b/plugins/providers/virtualbox/action/boot.rb
@@ -14,35 +14,9 @@ module VagrantPlugins
           # Start up the VM and wait for it to boot.
           env[:ui].info I18n.t("vagrant.actions.vm.boot.booting")
           env[:machine].provider.driver.start(boot_mode)
-          raise Vagrant::Errors::VMFailedToBoot if !wait_for_boot
 
           @app.call(env)
         end
-
-        def wait_for_boot
-          @env[:ui].info I18n.t("vagrant.actions.vm.boot.waiting")
-
-          @env[:machine].config.ssh.max_tries.to_i.times do |i|
-            if @env[:machine].communicate.ready?
-              @env[:ui].info I18n.t("vagrant.actions.vm.boot.ready")
-              return true
-            end
-
-            # Return true so that the vm_failed_to_boot error doesn't
-            # get shown
-            return true if @env[:interrupted]
-
-            # If the VM is not starting or running, something went wrong
-            # and we need to show a useful error.
-            state = @env[:machine].provider.state.id
-            raise Vagrant::Errors::VMFailedToRun if state != :starting && state != :running
-
-            sleep 2 if !@env["vagrant.test"]
-          end
-
-          @env[:ui].error I18n.t("vagrant.actions.vm.boot.failed")
-          false
-        end
       end
     end
   end
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index fa2b7093a..0f9d7f74b 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -1,5 +1,9 @@
 en:
   vagrant:
+    boot_completed: |-
+      Machine booted and ready!
+    boot_waiting: |-
+      Waiting for machine to boot. This may take a few minutes...
     cfengine_bootstrapping: |-
       Bootstrapping CFEngine with policy server: %{policy_server}...
     cfengine_bootstrapping_policy_hub: |-
@@ -144,6 +148,25 @@ en:
         Any errors that occurred are shown below.
 
         %{message}
+      boot_bad_state: |-
+        The guest machine entered an invalid state while waiting for it
+        to boot. Valid states are '%{valid}'. The machine is in the
+        '%{invalid}' state. Please verify everything is configured
+        properly and try again.
+      boot_timeout: |-
+        Timed out while waiting for the machine to boot. This means that
+        Vagrant was unable to communicate with the guest machine within
+        the configured ("config.ssh.timeout" value) time period. This can
+        mean a number of things.
+
+        If you're using a custom box, make sure that networking is properly
+        working and you're able to connect to the machine. It is a common
+        problem that networking isn't setup properly in these boxes.
+        Verify that authentication configurations are also setup properly,
+        as well.
+
+        If the box appears to be booting properly, you may want to increase
+        the timeout ("config.ssh.timeout") value.
       box_config_changing_box: |-
         While loading the Vagrantfile, the provider override specified
         a new box. This box, in turn, specified a different box. This isn't
@@ -815,9 +838,6 @@ en:
       vm:
         boot:
           booting: Booting VM...
-          waiting: Waiting for VM to boot. This can take a few minutes.
-          ready: VM booted and ready for use!
-          failed: Failed to connect to VM!
           failed_to_boot: |-
             Failed to connect to VM via SSH. Please verify the VM successfully booted
             by looking at the VirtualBox GUI.