diff --git a/Gemfile.lock b/Gemfile.lock
index 4f05fdf..ffc6056 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,26 +1,26 @@
 GIT
   remote: git://github.com/fgrehm/vagrant-global-status.git
-  revision: 860a7ce70ff4596621af492e47eace5631f47324
+  revision: a0295400a0e47756cbcb8f97ed9f4449b1fb6b56
   specs:
-    vagrant-global-status (0.1.0)
+    vagrant-global-status (0.1.1)
 
 GIT
   remote: git://github.com/fgrehm/vagrant-lxc.git
-  revision: 5ae82681cdedaf2a6f778e005dd65014fc7c2cec
+  revision: 225af5622767059708278db29d42941e93d41994
   specs:
-    vagrant-lxc (0.5.1.dev)
+    vagrant-lxc (0.6.4.dev)
 
 GIT
   remote: git://github.com/fgrehm/vagrant-pristine.git
-  revision: 5c400d7850fc5f98d9601b59f4c3bd74818650de
+  revision: 4638491786943bfbf6f115b1fc379f069963fe46
   specs:
-    vagrant-pristine (0.2.0)
+    vagrant-pristine (0.3.0)
 
 GIT
   remote: git://github.com/mitchellh/vagrant.git
-  revision: 16002d03c07f842a23497543129fa99f40f2bbc0
+  revision: 57e95323b6600b146167f0f14f83b22dd31dd03f
   specs:
-    vagrant (1.2.8.dev)
+    vagrant (1.3.6.dev)
       childprocess (~> 0.3.7)
       erubis (~> 2.7.0)
       i18n (~> 0.6.0)
@@ -56,7 +56,7 @@ GEM
     erubis (2.7.0)
     ffi (1.9.0)
     highline (1.6.19)
-    i18n (0.6.4)
+    i18n (0.6.5)
     ipaddress (0.8.0)
     json (1.7.7)
     librarian (0.1.0)
@@ -97,7 +97,7 @@ GEM
     thor (0.18.1)
     vagrant-librarian-chef (0.1.2)
       librarian-chef
-    vagrant-omnibus (1.1.0)
+    vagrant-omnibus (1.1.2)
     yajl-ruby (1.1.0)
 
 PLATFORMS
diff --git a/lib/vagrant-cachier/action/clean.rb b/lib/vagrant-cachier/action/clean.rb
index 84702d0..a2015bf 100644
--- a/lib/vagrant-cachier/action/clean.rb
+++ b/lib/vagrant-cachier/action/clean.rb
@@ -1,3 +1,5 @@
+require 'timeout'
+
 module VagrantPlugins
   module Cachier
     class Action
@@ -8,29 +10,54 @@ module VagrantPlugins
         end
 
         def call(env)
-          @env = env
+          @env     = env
+          @machine = env[:machine]
 
-          if env[:machine].state.id == :running && symlinks.any?
+          if symlinks.any?
             env[:ui].info I18n.t('vagrant_cachier.cleanup')
-            symlinks.each do |symlink|
-              remove_symlink symlink
+            if sshable?
+              symlinks.each do |symlink|
+                remove_symlink symlink
+              end
             end
 
-            File.delete env[:machine].data_dir.join('cache_dirs').to_s
+            File.delete @machine.data_dir.join('cache_dirs').to_s
           end
 
           @app.call env
         end
 
+        def sshable?
+          return if @machine.state.id != :running
+
+          # By default Vagrant will keep trying [1] to ssh connect to the VM for
+          # a long and we've got to prevent that from happening, so we just wait
+          # a few seconds and assume that the VM is halted / unresponsive and we
+          # carry on if it times out.
+          #   [1] - https://github.com/mitchellh/vagrant/blob/57e95323b6600b146167f0f14f83b22dd31dd03f/plugins/communicators/ssh/communicator.rb#L185-L200
+          begin
+            Timeout.timeout(35) do
+              while true
+                return true if @machine.communicate.ready?
+                sleep 0.5
+              end
+            end
+          rescue Timeout::Error
+            @env[:ui].warn(I18n.t('vagrant_cachier.unable_to_ssh'))
+          end
+
+          return false
+        end
+
         def symlinks
           # TODO: Check if file exists instead of a blank rescue
-          @symlinks ||= @env[:machine].data_dir.join('cache_dirs').read.split rescue []
+          @symlinks ||= @machine.data_dir.join('cache_dirs').read.split rescue []
         end
 
         def remove_symlink(symlink)
-          if @env[:machine].communicate.test("test -L #{symlink}")
+          if @machine.communicate.test("test -L #{symlink}")
             @logger.debug "Removing symlink for '#{symlink}'"
-            @env[:machine].communicate.sudo("unlink #{symlink}")
+            @machine.communicate.sudo("unlink #{symlink}")
           end
         end
       end
diff --git a/locales/en.yml b/locales/en.yml
index b54004d..b8147ad 100644
--- a/locales/en.yml
+++ b/locales/en.yml
@@ -11,6 +11,8 @@ en:
       '%{current_path}' and it will be moved to
       '%{new_path}' as it is the new path for keeping machine
       scoped cache dirs starting with the 0.3.0 version of the plugin.
+    unable_to_ssh: |-
+      vagrant-cachier was unable to SSH into the VM to remove symlinks!
   vagrant:
     errors:
       multiple_provider_specific_cache_dirs_found: |-