diff --git a/plugins/synced_folders/rsync/command/rsync_auto.rb b/plugins/synced_folders/rsync/command/rsync_auto.rb
index d66747ffa..097e68cc3 100644
--- a/plugins/synced_folders/rsync/command/rsync_auto.rb
+++ b/plugins/synced_folders/rsync/command/rsync_auto.rb
@@ -141,7 +141,7 @@ module VagrantPlugins
           Vagrant::Util::Busy.busy(callback) do
             listener.start
             queue.pop
-            listener.stop if listener.listen?
+            listener.stop if listener.state != :stopped
           end
 
           0
diff --git a/vagrant.gemspec b/vagrant.gemspec
index 415885270..e0589fa52 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -19,7 +19,7 @@ Gem::Specification.new do |s|
   s.add_dependency "childprocess", "~> 0.5.0"
   s.add_dependency "erubis", "~> 2.7.0"
   s.add_dependency "i18n", ">= 0.6.0", "<= 0.8.0"
-  s.add_dependency "listen", "~> 2.8.0"
+  s.add_dependency "listen", "~> 3.0.2"
   s.add_dependency "hashicorp-checkpoint", "~> 0.1.1"
   s.add_dependency "log4r", "~> 1.1.9", "< 1.1.11"
   s.add_dependency "net-ssh", ">= 2.6.6", "< 2.10.0"