diff --git a/CHANGELOG.md b/CHANGELOG.md
index edc335e72..f07788846 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@
   - Linux uses `shutdown -h` instead of `halt` to hopefully more consistently
     power off the system. [GH-575]
   - Tweaks to SSH to hopefully be more reliable in coming up.
+  - Helpful error message when SCP is unavailable in the guest. [GH-568]
 
 ## 0.8.10 (December 10, 2011)
 
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index a29d9dbe6..1a9b12170 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -245,6 +245,11 @@ module Vagrant
       error_key(:dotfile_error, "vagrant.actions.vm.persist")
     end
 
+    class SCPUnavailable < VagrantError
+      status_code(56)
+      error_key(:scp_unavailable)
+    end
+
     class SSHAuthenticationFailed < VagrantError
       status_code(11)
       error_key(:ssh_authentication_failed)
diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index 8cd92f2d5..025f98390 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -104,6 +104,12 @@ module Vagrant
           scp.upload!(from, to)
         end
       end
+    rescue Net::SCP::Error
+      # If we get the exit code of 127, then this means SCP is unavailable.
+      raise Errors::SCPUnavailable if e.message =~ /\(127\)/
+
+      # Otherwise, just raise the error up
+      raise
     end
 
     # Checks if this environment's machine is up (i.e. responding to SSH).
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 3f5cabe39..c4c432632 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -52,6 +52,9 @@ en:
       multi_vm_required: "A multi-vm environment is required for name specification to this command."
       multi_vm_target_required: "`vagrant %{command}` requires a specific VM name to target in a multi-VM environment."
       no_env: "No Vagrant environment detected. Run `vagrant init` to set one up."
+      scp_unavailable: |-
+        SSH server on the guest doesn't support SCP. Please install the necessary
+        software to enable SCP on your guest operating system.
       ssh_authentication_failed: |-
         SSH authentication failed! This is typically caused by the public/private
         keypair for the SSH user not being properly set on the guest VM. Please