diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 0a7b1f479..3db73cefb 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -432,6 +432,10 @@ module Vagrant
       error_key(:rsync_not_found)
     end
 
+    class RSyncNotInstalledInGuest < VagrantError
+      error_key(:rsync_not_installed_in_guest)
+    end
+
     class SCPPermissionDenied < VagrantError
       error_key(:scp_permission_denied)
     end
diff --git a/plugins/guests/darwin/cap/rsync.rb b/plugins/guests/darwin/cap/rsync.rb
new file mode 100644
index 000000000..3ddbe485e
--- /dev/null
+++ b/plugins/guests/darwin/cap/rsync.rb
@@ -0,0 +1,20 @@
+module VagrantPlugins
+  module GuestDarwin
+    module Cap
+      class RSync
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
+        def self.rsync_pre(machine, folder_opts)
+          username = machine.ssh_info[:username]
+
+          machine.communicate.tap do |comm|
+            comm.sudo("mkdir -p '#{folder_opts[:guestpath]}'")
+            comm.sudo("chown -R #{username} '#{folder_opts[:guestpath]}'")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/darwin/plugin.rb b/plugins/guests/darwin/plugin.rb
index 5b23b8f4f..a2fb0b2db 100644
--- a/plugins/guests/darwin/plugin.rb
+++ b/plugins/guests/darwin/plugin.rb
@@ -36,6 +36,16 @@ module VagrantPlugins
         Cap::MountVmwareSharedFolder
       end
 
+      guest_capability("darwin", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("darwin", "rsync_pre") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
       guest_capability("darwin", "shell_expand_guest_path") do
         require_relative "cap/shell_expand_guest_path"
         Cap::ShellExpandGuestPath
diff --git a/plugins/guests/debian/cap/rsync.rb b/plugins/guests/debian/cap/rsync.rb
new file mode 100644
index 000000000..80735cc9e
--- /dev/null
+++ b/plugins/guests/debian/cap/rsync.rb
@@ -0,0 +1,14 @@
+module VagrantPlugins
+  module GuestDebian
+    module Cap
+      class RSync
+        def self.rsync_install(machine)
+          machine.communicate.tap do |comm|
+            comm.sudo("apt-get -y update")
+            comm.sudo("apt-get -y install rsync")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/debian/plugin.rb b/plugins/guests/debian/plugin.rb
index 82c211bdf..0ba72ed5d 100644
--- a/plugins/guests/debian/plugin.rb
+++ b/plugins/guests/debian/plugin.rb
@@ -25,6 +25,11 @@ module VagrantPlugins
         require_relative "cap/nfs_client"
         Cap::NFSClient
       end
+
+      guest_capability("debian", "rsync_install") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/guests/freebsd/cap/rsync.rb b/plugins/guests/freebsd/cap/rsync.rb
new file mode 100644
index 000000000..3dc6d6718
--- /dev/null
+++ b/plugins/guests/freebsd/cap/rsync.rb
@@ -0,0 +1,26 @@
+module VagrantPlugins
+  module GuestFreeBSD
+    module Cap
+      class RSync
+        def self.rsync_install(machine)
+          machine.communicate.tap do |comm|
+            comm.sudo("pkg_add -r rsync")
+          end
+        end
+
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
+        def self.rsync_pre(machine, folder_opts)
+          username = machine.ssh_info[:username]
+
+          machine.communicate.tap do |comm|
+            comm.sudo("mkdir -p '#{folder_opts[:guestpath]}'", shell: "sh")
+            comm.sudo("chown -R #{username} '#{folder_opts[:guestpath]}'", shell: "sh")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/freebsd/plugin.rb b/plugins/guests/freebsd/plugin.rb
index 8e147087b..1cc9b449f 100644
--- a/plugins/guests/freebsd/plugin.rb
+++ b/plugins/guests/freebsd/plugin.rb
@@ -30,6 +30,21 @@ module VagrantPlugins
         require_relative "cap/mount_nfs_folder"
         Cap::MountNFSFolder
       end
+
+      guest_capability("freebsd", "rsync_install") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("freebsd", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("freebsd", "rsync_pre") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/guests/linux/cap/rsync.rb b/plugins/guests/linux/cap/rsync.rb
index 2bed51e33..5469b3a13 100644
--- a/plugins/guests/linux/cap/rsync.rb
+++ b/plugins/guests/linux/cap/rsync.rb
@@ -2,6 +2,10 @@ module VagrantPlugins
   module GuestLinux
     module Cap
       class RSync
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
         def self.rsync_pre(machine, folder_opts)
           username = machine.ssh_info[:username]
 
diff --git a/plugins/guests/linux/plugin.rb b/plugins/guests/linux/plugin.rb
index fb91b722c..9a93ab5b9 100644
--- a/plugins/guests/linux/plugin.rb
+++ b/plugins/guests/linux/plugin.rb
@@ -46,7 +46,11 @@ module VagrantPlugins
         Cap::ReadIPAddress
       end
 
-      # RSync synced folders
+      guest_capability("linux", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
       guest_capability("linux", "rsync_pre") do
         require_relative "cap/rsync"
         Cap::RSync
diff --git a/plugins/guests/netbsd/cap/rsync.rb b/plugins/guests/netbsd/cap/rsync.rb
new file mode 100644
index 000000000..1c7d4e72e
--- /dev/null
+++ b/plugins/guests/netbsd/cap/rsync.rb
@@ -0,0 +1,27 @@
+module VagrantPlugins
+  module GuestNetBSD
+    module Cap
+      class RSync
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
+        def self.rsync_install(machine)
+          machine.communicate.sudo(
+            'export PKG_PATH="http://ftp.NetBSD.org/pub/pkgsrc/packages/NetBSD/' \
+            '`uname -m`/`uname -r | cut -d. -f1-2`/All"; ' \
+            'pkg_add rsync')
+        end
+
+        def self.rsync_pre(machine, folder_opts)
+          username = machine.ssh_info[:username]
+
+          machine.communicate.tap do |comm|
+            comm.sudo("mkdir -p '#{folder_opts[:guestpath]}'")
+            comm.sudo("chown -R #{username} '#{folder_opts[:guestpath]}'")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/netbsd/plugin.rb b/plugins/guests/netbsd/plugin.rb
index ca55706fc..00f67144a 100644
--- a/plugins/guests/netbsd/plugin.rb
+++ b/plugins/guests/netbsd/plugin.rb
@@ -30,6 +30,21 @@ module VagrantPlugins
         require_relative "cap/mount_nfs_folder"
         Cap::MountNFSFolder
       end
+
+      guest_capability("netbsd", "rsync_install") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("netbsd", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("netbsd", "rsync_pre") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/guests/openbsd/cap/rsync.rb b/plugins/guests/openbsd/cap/rsync.rb
new file mode 100644
index 000000000..269f6e101
--- /dev/null
+++ b/plugins/guests/openbsd/cap/rsync.rb
@@ -0,0 +1,26 @@
+module VagrantPlugins
+  module GuestOpenBSD
+    module Cap
+      class RSync
+        def self.rsync_install(machine)
+          machine.communicate.tap do |comm|
+            comm.sudo("pkg_add -I rsync--")
+          end
+        end
+
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
+        def self.rsync_pre(machine, folder_opts)
+          username = machine.ssh_info[:username]
+
+          machine.communicate.tap do |comm|
+            comm.sudo("mkdir -p '#{folder_opts[:guestpath]}'")
+            comm.sudo("chown -R #{username} '#{folder_opts[:guestpath]}'")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/openbsd/plugin.rb b/plugins/guests/openbsd/plugin.rb
index fc1043a53..05d1217c0 100644
--- a/plugins/guests/openbsd/plugin.rb
+++ b/plugins/guests/openbsd/plugin.rb
@@ -30,6 +30,21 @@ module VagrantPlugins
         require_relative "cap/mount_nfs_folder"
         Cap::MountNFSFolder
       end
+
+      guest_capability("openbsd", "rsync_install") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("openbsd", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("openbsd", "rsync_pre") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/guests/redhat/cap/rsync.rb b/plugins/guests/redhat/cap/rsync.rb
new file mode 100644
index 000000000..9a1cfeeac
--- /dev/null
+++ b/plugins/guests/redhat/cap/rsync.rb
@@ -0,0 +1,13 @@
+module VagrantPlugins
+  module GuestRedHat
+    module Cap
+      class RSync
+        def self.rsync_install(machine)
+          machine.communicate.tap do |comm|
+            comm.sudo("yum -y install rsync")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/redhat/plugin.rb b/plugins/guests/redhat/plugin.rb
index 503b37423..56e6b8031 100644
--- a/plugins/guests/redhat/plugin.rb
+++ b/plugins/guests/redhat/plugin.rb
@@ -30,6 +30,11 @@ module VagrantPlugins
         require_relative "cap/nfs_client"
         Cap::NFSClient
       end
+
+      guest_capability("redhat", "rsync_install") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/guests/solaris/cap/rsync.rb b/plugins/guests/solaris/cap/rsync.rb
new file mode 100644
index 000000000..a470011b2
--- /dev/null
+++ b/plugins/guests/solaris/cap/rsync.rb
@@ -0,0 +1,20 @@
+module VagrantPlugins
+  module GuestSolaris
+    module Cap
+      class RSync
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
+        def self.rsync_pre(machine, folder_opts)
+          username = machine.ssh_info[:username]
+
+          machine.communicate.tap do |comm|
+            comm.sudo("mkdir -p '#{folder_opts[:guestpath]}'")
+            comm.sudo("chown -R #{username} '#{folder_opts[:guestpath]}'")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/solaris/plugin.rb b/plugins/guests/solaris/plugin.rb
index 9f1fc80d9..d7bb5e474 100644
--- a/plugins/guests/solaris/plugin.rb
+++ b/plugins/guests/solaris/plugin.rb
@@ -35,6 +35,16 @@ module VagrantPlugins
         require_relative "cap/mount_virtualbox_shared_folder"
         Cap::MountVirtualBoxSharedFolder
       end
+
+      guest_capability("solaris", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("solaris", "rsync_pre") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/guests/solaris11/cap/rsync.rb b/plugins/guests/solaris11/cap/rsync.rb
new file mode 100644
index 000000000..0175bf86d
--- /dev/null
+++ b/plugins/guests/solaris11/cap/rsync.rb
@@ -0,0 +1,20 @@
+module VagrantPlugins
+  module GuestSolaris11
+    module Cap
+      class RSync
+        def self.rsync_installed(machine)
+          machine.communicate.test("which rsync")
+        end
+
+        def self.rsync_pre(machine, folder_opts)
+          username = machine.ssh_info[:username]
+
+          machine.communicate.tap do |comm|
+            comm.sudo("mkdir -p '#{folder_opts[:guestpath]}'")
+            comm.sudo("chown -R #{username} '#{folder_opts[:guestpath]}'")
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/solaris11/plugin.rb b/plugins/guests/solaris11/plugin.rb
index fa6739584..707fd2bfc 100644
--- a/plugins/guests/solaris11/plugin.rb
+++ b/plugins/guests/solaris11/plugin.rb
@@ -39,6 +39,16 @@ module VagrantPlugins
         require_relative "cap/mount_virtualbox_shared_folder"
         Cap::MountVirtualBoxSharedFolder
       end
+
+      guest_capability("solaris11", "rsync_installed") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
+      guest_capability("solaris11", "rsync_pre") do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
     end
   end
 end
diff --git a/plugins/synced_folders/rsync/synced_folder.rb b/plugins/synced_folders/rsync/synced_folder.rb
index 416a1b06c..4e978f371 100644
--- a/plugins/synced_folders/rsync/synced_folder.rb
+++ b/plugins/synced_folders/rsync/synced_folder.rb
@@ -28,6 +28,16 @@ module VagrantPlugins
       end
 
       def enable(machine, folders, opts)
+        if machine.guest.capability?(:rsync_installed)
+          installed = machine.guest.capability(:rsync_installed)
+          if !installed
+            can_install = machine.guest.capability?(:rsync_install)
+            raise Vagrant::Errors::RSyncNotInstalledInGuest if !can_install
+            machine.ui.info I18n.t("vagrant.rsync_installing")
+            machine.guest.capability(:rsync_install)
+          end
+        end
+
         ssh_info = machine.ssh_info
 
         if ssh_info[:private_key_path].empty? && ssh_info[:password]
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index fd4590754..baffa7b12 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -99,6 +99,7 @@ en:
     rsync_folder: |-
       Rsyncing folder: %{hostpath} => %{guestpath}
     rsync_folder_excludes: "  - Exclude: %{excludes}"
+    rsync_installing: "Installing rsync to the VM..."
     rsync_ssh_password: |-
       The machine you're rsyncing folders to is configured to use
       password-based authentication. Vagrant can't script rsync to automatically
@@ -574,6 +575,11 @@ en:
       rsync_not_found: |-
         "rsync" could not be found on your PATH. Make sure that rsync
         is properly installed on your system and available on the PATH.
+      rsync_not_installed_in_guest: |-
+        "rsync" was not detected as installed in your guest machine. This
+        is required for rsync synced folders to work. In addition to this,
+        Vagrant doesn't know how to automatically install rsync for your
+        machine, so you must do this manually.
       scp_permission_denied: |-
         Failed to upload a file to the guest VM via SCP due to a permissions
         error. This is normally because the user running Vagrant doesn't have
diff --git a/test/unit/plugins/synced_folders/rsync/synced_folder_test.rb b/test/unit/plugins/synced_folders/rsync/synced_folder_test.rb
index 2b7df8781..2dae9cb82 100644
--- a/test/unit/plugins/synced_folders/rsync/synced_folder_test.rb
+++ b/test/unit/plugins/synced_folders/rsync/synced_folder_test.rb
@@ -48,6 +48,7 @@ describe VagrantPlugins::SyncedFolderRSync::SyncedFolder do
 
     before do
       machine.stub(ssh_info: ssh_info)
+      guest.stub(:capability?).with(:rsync_installed)
     end
 
     it "rsyncs each folder" do
@@ -64,5 +65,33 @@ describe VagrantPlugins::SyncedFolderRSync::SyncedFolder do
 
       subject.enable(machine, folders, {})
     end
+
+    it "installs rsync if capable" do
+      folders = [ [:foo, {}] ]
+
+      helper_class.stub(:rsync_single)
+
+      guest.stub(:capability?).with(:rsync_installed).and_return(true)
+      guest.stub(:capability?).with(:rsync_install).and_return(true)
+
+      expect(guest).to receive(:capability).with(:rsync_installed).and_return(false)
+      expect(guest).to receive(:capability).with(:rsync_install)
+
+      subject.enable(machine, folders, {})
+    end
+
+    it "errors if rsync not installable" do
+      folders = [ [:foo, {}] ]
+
+      helper_class.stub(:rsync_single)
+
+      guest.stub(:capability?).with(:rsync_installed).and_return(true)
+      guest.stub(:capability?).with(:rsync_install).and_return(false)
+
+      expect(guest).to receive(:capability).with(:rsync_installed).and_return(false)
+
+      expect { subject.enable(machine, folders, {}) }.
+        to raise_error(Vagrant::Errors::RSyncNotInstalledInGuest)
+    end
   end
 end