diff --git a/plugins/communicators/winssh/communicator.rb b/plugins/communicators/winssh/communicator.rb
index 37fe347da..e7de70675 100644
--- a/plugins/communicators/winssh/communicator.rb
+++ b/plugins/communicators/winssh/communicator.rb
@@ -33,7 +33,7 @@ module VagrantPlugins
 
           tfile = Tempfile.new('vagrant-ssh')
           remote_ext = shell == "powershell" ? "ps1" : "bat"
-          remote_name = "C:\\Windows\\Temp\\#{File.basename(tfile.path)}.#{remote_ext}"
+          remote_name = "#{machine_config_ssh.upload_directory}\\#{File.basename(tfile.path)}.#{remote_ext}"
 
           if shell == "powershell"
             base_cmd = "powershell -File #{remote_name}"
diff --git a/plugins/communicators/winssh/config.rb b/plugins/communicators/winssh/config.rb
index 4ad03d19f..e6cc9aec7 100644
--- a/plugins/communicators/winssh/config.rb
+++ b/plugins/communicators/winssh/config.rb
@@ -4,9 +4,17 @@ module VagrantPlugins
   module CommunicatorWinSSH
     class Config < VagrantPlugins::Kernel_V2::SSHConfig
 
+      attr_accessor :upload_directory
+
+      def initialize
+        super
+        @upload_directory = UNSET_VALUE
+      end
+
       def finalize!
         @shell = "cmd" if @shell == UNSET_VALUE
         @sudo_command = "%c" if @sudo_command == UNSET_VALUE
+        @upload_directory = "C:\\Windows\\Temp" if @upload_directory == UNSET_VALUE
         if @export_command_template == UNSET_VALUE
           if @shell == "cmd"
             @export_command_template = 'set %ENV_KEY%="%ENV_VALUE%"'
diff --git a/plugins/guests/windows/cap/public_key.rb b/plugins/guests/windows/cap/public_key.rb
new file mode 100644
index 000000000..c5ede693a
--- /dev/null
+++ b/plugins/guests/windows/cap/public_key.rb
@@ -0,0 +1,106 @@
+require "tempfile"
+
+module VagrantPlugins
+  module GuestWindows
+    module Cap
+      class PublicKey
+        def self.insert_public_key(machine, contents)
+          if machine.communicate.is_a?(CommunicatorWinSSH::Communicator)
+            winssh_insert_public_key(machine, contents)
+          else
+            raise Vagrant::Errors::SSHInsertKeyUnsupported
+          end
+        end
+
+        def self.remove_public_key(machine, contents)
+          if machine.communicate.is_a?(CommunicatorWinSSH::Communicator)
+            winssh_remove_public_key(machine, contents)
+          else
+            raise Vagrant::Errors::SSHInsertKeyUnsupported
+          end
+        end
+
+        def self.winssh_insert_public_key(machine, contents)
+          comm = machine.communicate
+          contents = contents.strip
+
+          directories = fetch_guest_paths(comm)
+          home_dir = directories[:home]
+          temp_dir = directories[:temp]
+
+          remote_ssh_dir = "#{home_dir}\\.ssh"
+          remote_upload_path = "#{temp_dir}\\vagrant-insert-pubkey-#{Time.now.to_i}"
+          remote_authkeys_path = "#{remote_ssh_dir}\authorized_keys"
+
+          # Ensure the user's ssh directory exists
+          comm.execute("dir \"#{remote_ssh_dir}\"\n if errorlevel 1 (mkdir \"#{remote_ssh_dir}\")", shell: "cmd")
+          remote_upload_path = "#{temp_dir}\\vagrant-insert-pubkey-#{Time.now.to_i}"
+          remote_authkeys_path = "#{remote_ssh_dir}\\authorized_keys"
+
+          keys_file = Tempfile.new("vagrant-windows-insert-public-key")
+          # Check if an authorized_keys file already exists
+          result = comm.execute("dir \"#{remote_authkeys_path}\"", shell: "cmd", error_check: false)
+          if result == 0
+            keys_file.close
+            comm.download(remote_authkeys_path, keys_file.path)
+            current_content = File.read(keys_file.path).split(/[\r\n]+/)
+            if !current_content.include?(contents)
+              current_content << contents
+            end
+            File.write(keys_file.path, current_content.join("\r\n") + "\r\n")
+          else
+            keys_file.puts(contents)
+            keys_file.close
+          end
+          keys_file.delete
+          comm.upload(keys_file.path, remote_upload_path)
+          comm.execute("move /y \"#{remote_upload_path}\" \"#{remote_authkeys_path}\"", shell: "cmd")
+        end
+
+        def self.winssh_remove_public_key(machine, contents)
+          comm = machine.communicate
+
+          directories = fetch_guest_paths(comm)
+          home_dir = directories[:home]
+          temp_dir = directories[:temp]
+
+          remote_ssh_dir = "#{home_dir}\\.ssh"
+          remote_upload_path = "#{temp_dir}\\vagrant-remove-pubkey-#{Time.now.to_i}"
+          remote_authkeys_path = "#{remote_ssh_dir}\\authorized_keys"
+
+          # Check if an authorized_keys file already exists
+          result = comm.execute("dir \"#{remote_authkeys_path}\"", shell: "cmd", error_check: false)
+          if result == 0
+            keys_file = Tempfile.new("vagrant-windows-remove-public-key")
+            keys_file.close
+            comm.download(remote_authkeys_path, keys_file.path)
+            current_content = File.read(keys_file.path).split(/[\r\n]+/)
+            current_content.delete(contents)
+            File.write(keys_file.path, current_content.join("\r\n") + "\r\n")
+            comm.upload(keys_file.path, remote_upload_path)
+            keys_file.delete
+            comm.execute("move /y \"#{remote_upload_path}\" \"#{remote_authkeys_path}\"", shell: "cmd")
+          end
+        end
+
+        # Fetch user's temporary and home directory paths from the Windows guest
+        #
+        # @param [Communicator]
+        # @return [Hash] {:temp, :home}
+        def self.fetch_guest_paths(communicator)
+          output = ""
+          communicator.execute("echo %TEMP%\necho %USERPROFILE%", shell: "cmd") do |type, data|
+            if type == :stdout
+              output << data
+            end
+          end
+          temp_dir, home_dir = output.strip.split(/[\r\n]+/)
+          if temp_dir.nil? || home_dir.nil?
+            raise Errors::PublicKeyDirectoryFailure
+          end
+          {temp: temp_dir, home: home_dir}
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/windows/errors.rb b/plugins/guests/windows/errors.rb
index e76753646..0b0536ed4 100644
--- a/plugins/guests/windows/errors.rb
+++ b/plugins/guests/windows/errors.rb
@@ -13,6 +13,10 @@ module VagrantPlugins
       class RenameComputerFailed < WindowsError
         error_key(:rename_computer_failed)
       end
+
+      class PublicKeyDirectoryFailure < WindowsError
+        error_key(:public_key_directory_failure)
+      end
     end
   end
 end
diff --git a/plugins/guests/windows/plugin.rb b/plugins/guests/windows/plugin.rb
index d4c5af98b..f7a71e959 100644
--- a/plugins/guests/windows/plugin.rb
+++ b/plugins/guests/windows/plugin.rb
@@ -74,6 +74,16 @@ module VagrantPlugins
         Cap::RSync
       end
 
+      guest_capability(:windows, :insert_public_key) do
+        require_relative "cap/public_key"
+        Cap::PublicKey
+      end
+
+      guest_capability(:windows, :remove_public_key) do
+        require_relative "cap/public_key"
+        Cap::PublicKey
+      end
+
       protected
 
       def self.init!
diff --git a/templates/locales/guest_windows.yml b/templates/locales/guest_windows.yml
index f9a3bf997..0e91a4ca0 100644
--- a/templates/locales/guest_windows.yml
+++ b/templates/locales/guest_windows.yml
@@ -1,6 +1,10 @@
 en:
   vagrant_windows:
     errors:
+      public_key_directory_failure: |-
+        Vagrant failed to properly discover the correct paths for the
+        temporary directory and user profile directory on the Windows
+        guest. Please ensure the guest is properly configured.
       network_winrm_required: |-
         Configuring networks on Windows requires the communicator to be
         set to WinRM. To do this, add the following to your Vagrantfile:
diff --git a/test/unit/plugins/communicators/winssh/communicator_test.rb b/test/unit/plugins/communicators/winssh/communicator_test.rb
index 459cac6d4..34812ac72 100644
--- a/test/unit/plugins/communicators/winssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/winssh/communicator_test.rb
@@ -22,7 +22,8 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
     double("winssh",
       insert_key: false,
       export_command_template: export_command_template,
-      shell: 'cmd'
+      shell: 'cmd',
+      upload_directory: "C:\\Windows\\Temp"
     )
   end
   # Configuration mock
diff --git a/test/unit/plugins/guests/windows/cap/insert_public_key_test.rb b/test/unit/plugins/guests/windows/cap/insert_public_key_test.rb
new file mode 100644
index 000000000..37d5a64f8
--- /dev/null
+++ b/test/unit/plugins/guests/windows/cap/insert_public_key_test.rb
@@ -0,0 +1,75 @@
+require "tempfile"
+require_relative "../../../../base"
+require_relative "../../../../../../plugins/communicators/winssh/communicator"
+
+describe "VagrantPlugins::GuestWindows::Cap::InsertPublicKey" do
+  let(:caps) do
+    VagrantPlugins::GuestWindows::Plugin
+      .components
+      .guest_capabilities[:windows]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+  let(:auth_keys_check_result){ 1 }
+
+  before do
+    @tempfile = Tempfile.new("vagrant-test")
+    allow(Tempfile).to receive(:new).and_return(@tempfile)
+    allow(comm).to receive(:is_a?).and_return(true)
+    allow(machine).to receive(:communicate).and_return(comm)
+
+    allow(comm).to receive(:execute).with(/echo .+/, shell: "cmd").and_yield(:stdout, "TEMP\r\nHOME\r\n")
+    allow(comm).to receive(:execute).with(/dir .+\.ssh/, shell: "cmd")
+    allow(comm).to receive(:execute).with(/dir .+authorized_keys/, shell: "cmd", error_check: false).and_return(auth_keys_check_result)
+  end
+
+  after do
+    @tempfile.delete
+  end
+
+  describe ".insert_public_key" do
+    let(:cap) { caps.get(:insert_public_key) }
+
+    context "when authorized_keys exists on guest" do
+      let(:auth_keys_check_result){ 0 }
+      before do
+        expect(@tempfile).to receive(:delete).and_return(true)
+        expect(@tempfile).to receive(:delete).and_call_original
+      end
+
+      it "inserts the public key" do
+        expect(comm).to receive(:download)
+        expect(comm).to receive(:upload)
+        expect(comm).to receive(:execute).with(/move .*/, shell: "cmd")
+        cap.insert_public_key(machine, "ssh-rsa ...")
+        expect(File.read(@tempfile.path)).to include("ssh-rsa ...")
+      end
+    end
+
+    context "when authorized_keys does not exist on guest" do
+      before do
+        expect(@tempfile).to receive(:delete).and_return(true)
+        expect(@tempfile).to receive(:delete).and_call_original
+      end
+
+      it "inserts the public key" do
+        expect(comm).to_not receive(:download)
+        expect(comm).to receive(:upload)
+        expect(comm).to receive(:execute).with(/move .*/, shell: "cmd")
+        cap.insert_public_key(machine, "ssh-rsa ...")
+        expect(File.read(@tempfile.path)).to include("ssh-rsa ...")
+      end
+    end
+
+    context "when required directories cannot be fetched from the guest" do
+      before do
+        expect(comm).to receive(:execute).with(/echo .+/, shell: "cmd").and_yield(:stdout, "TEMP\r\n")
+      end
+
+      it "should raise an error" do
+        expect{ cap.insert_public_key(machine, "ssh-rsa ...") }.to raise_error(VagrantPlugins::GuestWindows::Errors::PublicKeyDirectoryFailure)
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/windows/cap/remove_public_key_test.rb b/test/unit/plugins/guests/windows/cap/remove_public_key_test.rb
new file mode 100644
index 000000000..9fb2903dd
--- /dev/null
+++ b/test/unit/plugins/guests/windows/cap/remove_public_key_test.rb
@@ -0,0 +1,66 @@
+require "tempfile"
+require_relative "../../../../base"
+require_relative "../../../../../../plugins/communicators/winssh/communicator"
+
+describe "VagrantPlugins::GuestWindows::Cap::RemovePublicKey" do
+  let(:caps) do
+    VagrantPlugins::GuestWindows::Plugin
+      .components
+      .guest_capabilities[:windows]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+  let(:public_key_insecure){ "ssh-rsa...insecure" }
+  let(:public_key_other){ "ssh-rsa...other" }
+
+  let(:auth_keys_check_result){ 1 }
+
+  before do
+    @tempfile = Tempfile.new("vagrant-test")
+    @tempfile.puts(public_key_insecure)
+    @tempfile.puts(public_key_other)
+    @tempfile.flush
+    @tempfile.rewind
+    allow(Tempfile).to receive(:new).and_return(@tempfile)
+    allow(comm).to receive(:is_a?).and_return(true)
+    allow(machine).to receive(:communicate).and_return(comm)
+
+    allow(comm).to receive(:execute).with(/echo .+/, shell: "cmd").and_yield(:stdout, "TEMP\r\nHOME\r\n")
+    allow(comm).to receive(:execute).with(/dir .+authorized_keys/, shell: "cmd", error_check: false).and_return(auth_keys_check_result)
+  end
+
+  after do
+    @tempfile.delete
+  end
+
+  describe ".remove_public_key" do
+    let(:cap) { caps.get(:remove_public_key) }
+
+    context "when authorized_keys exists on guest" do
+      let(:auth_keys_check_result){ 0 }
+      before do
+        expect(@tempfile).to receive(:delete).and_return(true)
+        expect(@tempfile).to receive(:delete).and_call_original
+      end
+
+      it "removes the public key" do
+        expect(comm).to receive(:download)
+        expect(comm).to receive(:upload)
+        expect(comm).to receive(:execute).with(/move .*/, shell: "cmd")
+        cap.remove_public_key(machine, public_key_insecure)
+        expect(File.read(@tempfile.path)).to include(public_key_other)
+        expect(File.read(@tempfile.path)).to_not include(public_key_insecure)
+      end
+    end
+
+    context "when authorized_keys does not exist on guest" do
+      it "does nothing" do
+        expect(comm).to_not receive(:download)
+        expect(comm).to_not receive(:upload)
+        expect(comm).to_not receive(:execute).with(/move .*/, shell: "cmd")
+        cap.remove_public_key(machine, public_key_insecure)
+      end
+    end
+  end
+end
diff --git a/test/unit/vagrant/util/subprocess_test.rb b/test/unit/vagrant/util/subprocess_test.rb
index d20a7fffd..94ba4225f 100644
--- a/test/unit/vagrant/util/subprocess_test.rb
+++ b/test/unit/vagrant/util/subprocess_test.rb
@@ -66,7 +66,7 @@ describe Vagrant::Util::Subprocess do
       it "should return true" do
         sp = described_class.new("sleep", "5")
         thread = Thread.new{ sp.execute }
-        sleep(0.1)
+        sleep(0.3)
         expect(sp.running?).to be_true
         sp.stop
         thread.join
diff --git a/website/source/docs/vagrantfile/winssh_settings.html.md b/website/source/docs/vagrantfile/winssh_settings.html.md
index 4c0da9753..6722100eb 100644
--- a/website/source/docs/vagrantfile/winssh_settings.html.md
+++ b/website/source/docs/vagrantfile/winssh_settings.html.md
@@ -161,3 +161,8 @@ config.winssh.export_command_template = '$env:%ENV_KEY%="%ENV_VALUE%"'
 with `sudo`. This defaults to `%c` (assumes vagrant user is an administator
 and needs no escalation). The `%c` will be replaced by the command that is
 being executed.
+
+<hr>
+
+`config.winssh.upload_directory` - The upload directory used on the guest
+to store scripts for execute. This is set to `C:\Windows\Temp` by default.