diff --git a/lib/vagrant/action/general/package.rb b/lib/vagrant/action/general/package.rb
index ee7e30ec3..99c0002ec 100644
--- a/lib/vagrant/action/general/package.rb
+++ b/lib/vagrant/action/general/package.rb
@@ -1,4 +1,5 @@
 require 'fileutils'
+require "pathname"
 
 require 'vagrant/util/safe_chdir'
 require 'vagrant/util/subprocess'
@@ -36,6 +37,9 @@ module Vagrant
 
           @app.call(env)
 
+          @env[:ui].info I18n.t("vagrant.actions.general.package.compressing", tar_path: tar_path)
+          copy_include_files
+          setup_private_key
           compress
         end
 
@@ -81,11 +85,6 @@ module Vagrant
 
         # Compress the exported file into a package
         def compress
-          @env[:ui].info I18n.t("vagrant.actions.general.package.compressing", tar_path: tar_path)
-
-          # Copy over the included files
-          copy_include_files
-
           # Get the output path. We have to do this up here so that the
           # pwd returns the proper thing.
           output_path = tar_path.to_s
@@ -100,6 +99,39 @@ module Vagrant
           end
         end
 
+        # This will copy the generated private key into the box and use
+        # it for SSH by default. We have to do this because we now generate
+        # random keypairs on boot, so packaged boxes would stop working
+        # without this.
+        def setup_private_key
+          # If we don't have machine, we do nothing (weird)
+          return if !@env[:machine]
+
+          # If we don't have a data dir, we also do nothing (base package)
+          return if !@env[:machine].data_dir
+
+          # If we don't have a generated private key, we do nothing
+          path = @env[:machine].data_dir.join("private_key")
+          return if !path.file?
+
+          # Copy it into our box directory
+          dir = Pathname.new(@env["package.directory"])
+          new_path = dir.join("vagrant_private_key")
+          FileUtils.cp(path, new_path)
+
+          # Append it to the Vagrantfile (or create a Vagrantfile)
+          vf_path = dir.join("Vagrantfile")
+          mode = "w+"
+          mode = "a" if vf_path.file?
+          vf_path.open(mode) do |f|
+            f.binmode
+            f.puts
+            f.puts %Q[Vagrant.configure("2") do |config|]
+            f.puts %Q[  config.ssh.private_key_path = File.expand_path("../vagrant_private_key", __FILE__)]
+            f.puts %Q[end]
+          end
+        end
+
         # Path to the final box output file
         def tar_path
           File.expand_path(@env["package.output"], FileUtils.pwd)
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index b1ec6f35c..623073a97 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -620,6 +620,10 @@ module Vagrant
       error_key(:ssh_invalid_shell)
     end
 
+    class SSHInsertKeyUnsupported < VagrantError
+      error_key(:ssh_insert_key_unsupported)
+    end
+
     class SSHIsPuttyLink < VagrantError
       error_key(:ssh_is_putty_link)
     end
diff --git a/lib/vagrant/util/keypair.rb b/lib/vagrant/util/keypair.rb
new file mode 100644
index 000000000..7fec84b2a
--- /dev/null
+++ b/lib/vagrant/util/keypair.rb
@@ -0,0 +1,46 @@
+require "base64"
+require "openssl"
+
+module Vagrant
+  module Util
+    class Keypair
+      # Creates an SSH keypair and returns it.
+      #
+      # @param [String] password Password for the key, or nil for no password.
+      # @return [Array<String, String, String>] PEM-encoded public and private key,
+      #   respectively. The final element is the OpenSSH encoded public
+      #   key.
+      def self.create(password=nil)
+        rsa_key     = OpenSSL::PKey::RSA.new(2048)
+        public_key  = rsa_key.public_key
+        private_key = rsa_key.to_pem
+
+        if password
+          cipher      = OpenSSL::Cipher::Cipher.new('des3')
+          private_key = rsa_key.to_pem(cipher, password)
+        end
+
+        # Generate the binary necessary for the OpenSSH public key.
+        binary = [7].pack("N")
+        binary += "ssh-rsa"
+        ["e", "n"].each do |m|
+          val  = public_key.send(m)
+          data = val.to_s(2)
+
+          first_byte = data[0,1].unpack("c").first
+          if val < 0
+            data[0] = [0x80 & first_byte].pack("c")
+          elsif first_byte < 0
+            data = 0.chr + data
+          end
+
+          binary += [data.length].pack("N") + data
+        end
+
+        openssh_key = "ssh-rsa #{Base64.encode64(binary).gsub("\n", "")} vagrant"
+        public_key  = public_key.to_pem
+        return [public_key, private_key, openssh_key]
+      end
+    end
+  end
+end
diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index cb9452d1c..35506e31e 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -11,6 +11,7 @@ require 'net/scp'
 
 require 'vagrant/util/ansi_escape_code_remover'
 require 'vagrant/util/file_mode'
+require 'vagrant/util/keypair'
 require 'vagrant/util/platform'
 require 'vagrant/util/retryable'
 
@@ -88,6 +89,8 @@ module VagrantPlugins
               raise
             rescue Vagrant::Errors::SSHKeyBadPermissions
               raise
+            rescue Vagrant::Errors::SSHInsertKeyUnsupported
+              raise
             rescue Vagrant::Errors::VagrantError => e
               # Ignore it, SSH is not ready, some other error.
             end
@@ -142,20 +145,41 @@ module VagrantPlugins
 
         # If we used a password, then insert the insecure key
         ssh_info = @machine.ssh_info
-        if ssh_info[:password] && ssh_info[:private_key_path].empty?
-          @logger.info("Inserting insecure key to avoid password")
-          @machine.ui.info(I18n.t("vagrant.inserting_insecure_key"))
-          @machine.guest.capability(
-            :insert_public_key,
-            Vagrant.source_root.join("keys", "vagrant.pub").read.chomp)
+        insert   = ssh_info[:password] && ssh_info[:private_key_path].empty?
+        ssh_info[:private_key_path].each do |pk|
+          if insecure_key?(pk)
+            insert = true
+            @machine.ui.detail("\n"+I18n.t("vagrant.inserting_insecure_detected"))
+            break
+          end
+        end
+
+        if insert
+          # If we don't have the power to insert/remove keys, then its an error
+          cap = @machine.guest.capability?(:insert_public_key) &&
+            @machine.guest.capability?(:remove_public_key)
+          raise Vagrant::Errors::SSHInsertKeyUnsupported if !cap
+
+          _pub, priv, openssh = Vagrant::Util::Keypair.create
+
+          @logger.info("Inserting key to avoid password: #{openssh}")
+          @machine.ui.detail("\n"+I18n.t("vagrant.inserting_random_key"))
+          @machine.guest.capability(:insert_public_key, openssh)
 
           # Write out the private key in the data dir so that the
           # machine automatically picks it up.
           @machine.data_dir.join("private_key").open("w+") do |f|
-            f.write(Vagrant.source_root.join("keys", "vagrant").read)
+            f.write(priv)
           end
 
-          @machine.ui.info(I18n.t("vagrant.inserted_key"))
+          # Remove the old key if it exists
+          @machine.ui.detail(I18n.t("vagrant.inserting_remove_key"))
+          @machine.guest.capability(
+            :remove_public_key,
+            Vagrant.source_root.join("keys", "vagrant.pub").read.chomp)
+
+          # Done, restart.
+          @machine.ui.detail(I18n.t("vagrant.inserted_key"))
           @connection.close
           @connection = nil
 
@@ -597,6 +621,16 @@ module VagrantPlugins
         # Otherwise, just raise the error up
         raise
       end
+
+      # This will test whether path is the Vagrant insecure private key.
+      #
+      # @param [String] path
+      def insecure_key?(path)
+        return false if !path
+        return false if !File.file?(path)
+        source_path = Vagrant.source_root.join("keys", "vagrant")
+        return File.read(path).chomp == source_path.read.chomp
+      end
     end
   end
 end
diff --git a/plugins/guests/freebsd/cap/remove_public_key.rb b/plugins/guests/freebsd/cap/remove_public_key.rb
new file mode 100644
index 000000000..13abc864b
--- /dev/null
+++ b/plugins/guests/freebsd/cap/remove_public_key.rb
@@ -0,0 +1,21 @@
+require "vagrant/util/shell_quote"
+
+module VagrantPlugins
+  module GuestFreeBSD
+    module Cap
+      class RemovePublicKey
+        def self.remove_public_key(machine, contents)
+          contents = contents.chomp
+          contents = Vagrant::Util::ShellQuote.escape(contents, "'")
+
+          machine.communicate.tap do |comm|
+            if comm.test("test -f ~/.ssh/authorized_keys")
+              comm.execute(
+                "sed -i '/^.*#{contents}.*$/d' ~/.ssh/authorized_keys")
+            end
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/freebsd/plugin.rb b/plugins/guests/freebsd/plugin.rb
index 49aa3298b..a4ece8de2 100644
--- a/plugins/guests/freebsd/plugin.rb
+++ b/plugins/guests/freebsd/plugin.rb
@@ -36,6 +36,11 @@ module VagrantPlugins
         Cap::MountNFSFolder
       end
 
+      guest_capability("freebsd", "remove_public_key") do
+        require_relative "cap/remove_public_key"
+        Cap::RemovePublicKey
+      end
+
       guest_capability("freebsd", "rsync_install") do
         require_relative "cap/rsync"
         Cap::RSync
diff --git a/plugins/guests/linux/cap/remove_public_key.rb b/plugins/guests/linux/cap/remove_public_key.rb
new file mode 100644
index 000000000..a8d773a40
--- /dev/null
+++ b/plugins/guests/linux/cap/remove_public_key.rb
@@ -0,0 +1,21 @@
+require "vagrant/util/shell_quote"
+
+module VagrantPlugins
+  module GuestLinux
+    module Cap
+      class RemovePublicKey
+        def self.remove_public_key(machine, contents)
+          contents = contents.chomp
+          contents = Vagrant::Util::ShellQuote.escape(contents, "'")
+
+          machine.communicate.tap do |comm|
+            if comm.test("test -f ~/.ssh/authorized_keys")
+              comm.execute(
+                "sed -i '/^.*#{contents}.*$/d' ~/.ssh/authorized_keys")
+            end
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/linux/plugin.rb b/plugins/guests/linux/plugin.rb
index a2bb1167c..cadd4aa95 100644
--- a/plugins/guests/linux/plugin.rb
+++ b/plugins/guests/linux/plugin.rb
@@ -62,6 +62,11 @@ module VagrantPlugins
         Cap::ReadIPAddress
       end
 
+      guest_capability("linux", "remove_public_key") do
+        require_relative "cap/remove_public_key"
+        Cap::RemovePublicKey
+      end
+
       guest_capability("linux", "rsync_installed") do
         require_relative "cap/rsync"
         Cap::RSync
diff --git a/plugins/guests/netbsd/cap/remove_public_key.rb b/plugins/guests/netbsd/cap/remove_public_key.rb
new file mode 100644
index 000000000..d25e97679
--- /dev/null
+++ b/plugins/guests/netbsd/cap/remove_public_key.rb
@@ -0,0 +1,21 @@
+require "vagrant/util/shell_quote"
+
+module VagrantPlugins
+  module GuestNetBSD
+    module Cap
+      class RemovePublicKey
+        def self.remove_public_key(machine, contents)
+          contents = contents.chomp
+          contents = Vagrant::Util::ShellQuote.escape(contents, "'")
+
+          machine.communicate.tap do |comm|
+            if comm.test("test -f ~/.ssh/authorized_keys")
+              comm.execute(
+                "sed -i '/^.*#{contents}.*$/d' ~/.ssh/authorized_keys")
+            end
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/netbsd/plugin.rb b/plugins/guests/netbsd/plugin.rb
index 490c73644..9636c6630 100644
--- a/plugins/guests/netbsd/plugin.rb
+++ b/plugins/guests/netbsd/plugin.rb
@@ -36,6 +36,11 @@ module VagrantPlugins
         Cap::MountNFSFolder
       end
 
+      guest_capability("netbsd", "remove_public_key") do
+        require_relative "cap/remove_public_key"
+        Cap::RemovePublicKey
+      end
+
       guest_capability("netbsd", "rsync_install") do
         require_relative "cap/rsync"
         Cap::RSync
diff --git a/plugins/guests/openbsd/cap/remove_public_key.rb b/plugins/guests/openbsd/cap/remove_public_key.rb
new file mode 100644
index 000000000..94cfce03b
--- /dev/null
+++ b/plugins/guests/openbsd/cap/remove_public_key.rb
@@ -0,0 +1,21 @@
+require "vagrant/util/shell_quote"
+
+module VagrantPlugins
+  module GuestOpenBSD
+    module Cap
+      class RemovePublicKey
+        def self.remove_public_key(machine, contents)
+          contents = contents.chomp
+          contents = Vagrant::Util::ShellQuote.escape(contents, "'")
+
+          machine.communicate.tap do |comm|
+            if comm.test("test -f ~/.ssh/authorized_keys")
+              comm.execute(
+                "sed -i '/^.*#{contents}.*$/d' ~/.ssh/authorized_keys")
+            end
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/openbsd/plugin.rb b/plugins/guests/openbsd/plugin.rb
index 7a64b16d6..a1ddfe9c1 100644
--- a/plugins/guests/openbsd/plugin.rb
+++ b/plugins/guests/openbsd/plugin.rb
@@ -36,6 +36,11 @@ module VagrantPlugins
         Cap::MountNFSFolder
       end
 
+      guest_capability("openbsd", "remove_public_key") do
+        require_relative "cap/remove_public_key"
+        Cap::RemovePublicKey
+      end
+
       guest_capability("openbsd", "rsync_install") do
         require_relative "cap/rsync"
         Cap::RSync
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 9fc465aac..333091fbb 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -130,8 +130,13 @@ en:
       Starting Docker containers...
     inserted_key: |-
       Key inserted! Disconnecting and reconnecting using new SSH key...
-    inserting_insecure_key: |-
-      Inserting Vagrant public key within guest...
+    inserting_insecure_detected: |-
+      Vagrant insecure key detected. Vagrant will automatically replace
+      this with a newly generated keypair for better security.
+    inserting_random_key: |-
+      Inserting generated public key within guest...
+    inserting_remove_key: |-
+      Removing insecure key from the guest if its present...
     list_commands: |-
       Below is a listing of all available Vagrant commands and a brief
       description of what they do.
@@ -1071,6 +1076,16 @@ en:
         using a shell that is unavailable on the system. Please verify
         you're using the full path to the shell and that the shell is
         executable by the SSH user.
+      ssh_insert_key_unsupported: |-
+        Vagrant is configured to generate a random keypair and insert it
+        onto the guest machine, but it appears Vagrant doesn't know how to do
+        this with your guest OS. Please disable key insertion by setting
+        `config.ssh.insert_key = false` in the Vagrantfile.
+
+        After doing so, run `vagrant reload` for the setting to take effect.
+
+        If you'd like Vagrant to learn how to insert keys on this OS, please
+        open an issue with details about your environment.
       ssh_is_putty_link: |-
         The `ssh` executable found in the PATH is a PuTTY Link SSH client.
         Vagrant is only compatible with OpenSSH SSH clients. Please install
diff --git a/test/unit/vagrant/util/keypair_test.rb b/test/unit/vagrant/util/keypair_test.rb
new file mode 100644
index 000000000..30ab76eba
--- /dev/null
+++ b/test/unit/vagrant/util/keypair_test.rb
@@ -0,0 +1,34 @@
+require "openssl"
+
+require File.expand_path("../../../base", __FILE__)
+
+require "vagrant/util/keypair"
+
+describe Vagrant::Util::Keypair do
+  describe ".create" do
+    it "generates a usable keypair with no password" do
+      # I don't know how to validate the final return value yet...
+      pubkey, privkey, _ = described_class.create
+
+      pubkey  = OpenSSL::PKey::RSA.new(pubkey)
+      privkey = OpenSSL::PKey::RSA.new(privkey)
+
+      encrypted = pubkey.public_encrypt("foo")
+      decrypted = privkey.private_decrypt(encrypted)
+
+      expect(decrypted).to eq("foo")
+    end
+
+    it "generates a keypair that requires a password" do
+      pubkey, privkey, _ = described_class.create("password")
+
+      pubkey  = OpenSSL::PKey::RSA.new(pubkey)
+      privkey = OpenSSL::PKey::RSA.new(privkey, "password")
+
+      encrypted = pubkey.public_encrypt("foo")
+      decrypted = privkey.private_decrypt(encrypted)
+
+      expect(decrypted).to eq("foo")
+    end
+  end
+end
diff --git a/website/docs/source/v2/boxes/base.html.md b/website/docs/source/v2/boxes/base.html.md
index 7e34bf1b5..e771187a0 100644
--- a/website/docs/source/v2/boxes/base.html.md
+++ b/website/docs/source/v2/boxes/base.html.md
@@ -116,6 +116,10 @@ that OpenSSH is very picky about file permissions. Therefore, make sure
 that `~/.ssh` has `0700` permissions and the authorized keys file has
 `0600` permissions.
 
+When Vagrant boots a box and detects the insecure keypair, it will
+automatically replace it with a randomly generated keypair for additional
+security while the box is running.
+
 ### Root Password: "vagrant"
 
 Vagrant doesn't actually use or expect any root password. However, having