diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2a3d31849..1515dfa72 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,8 @@ BUG FIXES:
       of Vagrant. [GH-3386]
   - core: Don't error if network problems cause box update check to
       fail [GH-3391]
+  - commands/rsync-auto: Don't crash if the machine can't be communicated
+      to. [GH-3419]
   - guests/fedora: Fix hostname setting. [GH-3382]
   - guests/fedora: Support predictable network interface names for
       public/private networks. [GH-3207]
diff --git a/plugins/synced_folders/rsync/command/rsync_auto.rb b/plugins/synced_folders/rsync/command/rsync_auto.rb
index 8e1951214..48ac287e5 100644
--- a/plugins/synced_folders/rsync/command/rsync_auto.rb
+++ b/plugins/synced_folders/rsync/command/rsync_auto.rb
@@ -112,7 +112,14 @@ module VagrantPlugins
           tosync.each do |folders|
             folders.each do |opts|
               ssh_info = opts[:machine].ssh_info
-              RsyncHelper.rsync_single(opts[:machine], ssh_info, opts[:opts])
+              begin
+                RsyncHelper.rsync_single(opts[:machine], ssh_info, opts[:opts])
+              rescue Vagrant::Errors::MachineGuestNotReady
+                # Error communicating to the machine, probably a reload or
+                # halt is happening. Just notify the user but don't fail out.
+                opts[:machine].ui.error(I18n.t(
+                  "vagrant.rsync_communicator_not_ready_callback"))
+              end
             end
           end
         end
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 9b85a2b9a..487c9a87d 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -159,6 +159,10 @@ en:
     rsync_communicator_not_ready: |-
       The machine is reporting that it is not ready for rsync to
       communiate with it. Verify that this machine is properly running.
+    rsync_communicator_not_ready_callback: |-
+      Failed to connect to remote machine. This is usually caused by the
+      machine rebooting or being halted. Please make sure the machine is
+      running, and modify a file to try again.
     rsync_folder: |-
       Rsyncing folder: %{hostpath} => %{guestpath}
     rsync_folder_excludes: "  - Exclude: %{excludes}"
diff --git a/test/unit/plugins/synced_folders/rsync/command/rsync_auto_test.rb b/test/unit/plugins/synced_folders/rsync/command/rsync_auto_test.rb
index bb8982b9f..7324b7962 100644
--- a/test/unit/plugins/synced_folders/rsync/command/rsync_auto_test.rb
+++ b/test/unit/plugins/synced_folders/rsync/command/rsync_auto_test.rb
@@ -30,6 +30,9 @@ describe VagrantPlugins::SyncedFolderRSync::Command::RsyncAuto do
     def machine_stub(name)
       double(name).tap do |m|
         m.stub(ssh_info: ssh_info)
+        m.stub(ui: double("ui"))
+
+        m.ui.stub(error: nil)
       end
     end
 
@@ -95,5 +98,27 @@ describe VagrantPlugins::SyncedFolderRSync::Command::RsyncAuto do
       r = ["/foo/bar"]
       subject.callback(paths, m, a, r)
     end
+
+    it "doesn't fail if guest error occurs" do
+      paths["/foo"] = [
+        { machine: machine_stub("m1"), opts: double("opts_m1") },
+        { machine: machine_stub("m2"), opts: double("opts_m2") },
+      ]
+      paths["/bar"] = [
+        { machine: machine_stub("m3"), opts: double("opts_m3") },
+      ]
+
+      paths["/foo"].each do |data|
+        expect(helper_class).to receive(:rsync_single).
+          with(data[:machine], data[:machine].ssh_info, data[:opts]).
+          and_raise(Vagrant::Errors::MachineGuestNotReady)
+      end
+
+      m = []
+      a = []
+      r = ["/foo/bar"]
+      expect { subject.callback(paths, m, a, r) }.
+        to_not raise_error
+    end
   end
 end