diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 44bed4d4c..90e5c42c1 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -436,6 +436,10 @@ module Vagrant
       error_key(:machine_action_locked)
     end
 
+    class MachineFolderNotAccessible < VagrantError
+      error_key(:machine_folder_not_accessible)
+    end
+
     class MachineGuestNotReady < VagrantError
       error_key(:machine_guest_not_ready)
     end
diff --git a/plugins/providers/virtualbox/action/clean_machine_folder.rb b/plugins/providers/virtualbox/action/clean_machine_folder.rb
index 3007cbd0f..d4fdf5203 100644
--- a/plugins/providers/virtualbox/action/clean_machine_folder.rb
+++ b/plugins/providers/virtualbox/action/clean_machine_folder.rb
@@ -13,7 +13,16 @@ module VagrantPlugins
         end
 
         def call(env)
-          clean_machine_folder(env[:machine].provider.driver.read_machine_folder)
+          machine_folder = env[:machine].provider.driver.read_machine_folder
+
+          begin
+            clean_machine_folder(machine_folder)
+          rescue Errno::EPERM
+            raise Vagrant::Errors::MachineFolderNotAccessible,
+              name: env[:machine].name,
+              path: machine_folder
+          end
+
           @app.call(env)
         end
 
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 333addb8a..72737a7b8 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -964,6 +964,15 @@ en:
         If you believe this message is in error, please check the process
         listing for any "ruby" or "vagrant" processes and kill them. Then
         try again.
+      machine_folder_not_accessible: |-
+        Vagrant attempted to clean the machine folder for the machine '%{name}'
+        but does not have permission to read the following path:
+
+        %{path}
+
+        Please ensure that Vagrant has the proper permissions to access the path
+        above. You may need to grant this permission to the terminal emulator
+        running Vagrant as well.
       machine_guest_not_ready: |-
         Guest-specific operations were attempted on a machine that is not
         ready for guest communication. This should not happen and a bug
diff --git a/test/unit/plugins/providers/virtualbox/action/clean_machine_folder_test.rb b/test/unit/plugins/providers/virtualbox/action/clean_machine_folder_test.rb
new file mode 100644
index 000000000..896c4842f
--- /dev/null
+++ b/test/unit/plugins/providers/virtualbox/action/clean_machine_folder_test.rb
@@ -0,0 +1,25 @@
+require_relative '../base'
+
+describe VagrantPlugins::ProviderVirtualBox::Action::CleanMachineFolder do
+  let(:app) { double("app") }
+  let(:driver) { double("driver") }
+  let(:machine) { double("machine", provider: double("provider", driver: driver), name: "") }
+  let(:env) {
+    { machine: machine }
+  }
+  let(:subject) { described_class.new(app, env) }
+
+  before do
+    allow(driver).to receive(:read_machine_folder)
+  end
+
+  context "machine folder is not accessible" do
+    before do
+      allow(subject).to receive(:clean_machine_folder).and_raise(Errno::EPERM)
+    end
+
+    it "raises an error" do
+      expect { subject.call(env) }.to raise_error(Vagrant::Errors::MachineFolderNotAccessible)
+    end
+  end
+end
diff --git a/website/source/docs/other/macos-catalina.html.md b/website/source/docs/other/macos-catalina.html.md
new file mode 100644
index 000000000..5fdd9d81a
--- /dev/null
+++ b/website/source/docs/other/macos-catalina.html.md
@@ -0,0 +1,32 @@
+---
+layout: "docs"
+page_title: "Vagrant and macOS Catalina"
+sidebar_current: "other-macos-catalina"
+description: |-
+  An overview of using Vagrant on macOS Catalina.
+---
+
+# Vagrant and macOS Catalina
+
+The latest version of macOS (Catalina) includes security changes that prevent
+applications from accessing data in your Documents, Desktop, and Downloads
+folders without explicit permission. If you keep any virtual machine files in
+these folders, you will need to allow access to these folders for your terminal
+emulator.
+
+Initially when you try to access one of these folders from the command line, you
+should see a popup that says something like:
+
+> “Terminal” would like to access files in your Documents folder.
+
+Click "OK" to grant those permissions.
+
+If you click "Don't Allow" and find that you need to grant access later on, you
+can go to "System Preferences" -> "Security & Privacy" -> "Files and Folders"
+and you should see your terminal emulator there. Click on the lock, and then
+click on the checkbox next to the folder that contains the files that Vagrant
+needs to access.
+
+Note that granting the `vagrant` binary "Full Disk Access" is not sufficient or
+necessary. If Terminal (or iTerm2/Hyper/etc.) is granted access to a particular
+folder, then Vagrant will also be able to access that folder.