diff --git a/plugins/communicators/winrm/config.rb b/plugins/communicators/winrm/config.rb
index 6e4a44338..79901d503 100644
--- a/plugins/communicators/winrm/config.rb
+++ b/plugins/communicators/winrm/config.rb
@@ -7,6 +7,7 @@ module VagrantPlugins
       attr_accessor :port
       attr_accessor :guest_port
       attr_accessor :max_tries
+      attr_accessor :retry_delay
       attr_accessor :timeout
       attr_accessor :transport
       attr_accessor :ssl_peer_verification
@@ -18,6 +19,7 @@ module VagrantPlugins
         @port                   = UNSET_VALUE
         @guest_port             = UNSET_VALUE
         @max_tries              = UNSET_VALUE
+        @retry_delay            = UNSET_VALUE
         @timeout                = UNSET_VALUE
         @transport              = UNSET_VALUE
         @ssl_peer_verification  = UNSET_VALUE
@@ -31,20 +33,22 @@ module VagrantPlugins
         is_ssl = @transport == :ssl
         @port = (is_ssl ? 5986 : 5985)       if @port == UNSET_VALUE
         @guest_port = (is_ssl ? 5986 : 5985) if @guest_port == UNSET_VALUE
-        @max_tries = 20       if @max_tries == UNSET_VALUE
-        @timeout = 1800       if @timeout == UNSET_VALUE
+        @max_tries = 20        if @max_tries == UNSET_VALUE
+        @retry_delay = 2       if @retry_delay == UNSET_VALUE
+        @timeout = 1800        if @timeout == UNSET_VALUE
         @ssl_peer_verification = true if @ssl_peer_verification == UNSET_VALUE
       end
 
       def validate(machine)
         errors = []
 
-        errors << "winrm.username cannot be nil."   if @username.nil?
-        errors << "winrm.password cannot be nil."   if @password.nil?
-        errors << "winrm.port cannot be nil."       if @port.nil?
-        errors << "winrm.guest_port cannot be nil." if @guest_port.nil?
-        errors << "winrm.max_tries cannot be nil."  if @max_tries.nil?
-        errors << "winrm.timeout cannot be nil."    if @timeout.nil?
+        errors << "winrm.username cannot be nil."    if @username.nil?
+        errors << "winrm.password cannot be nil."    if @password.nil?
+        errors << "winrm.port cannot be nil."        if @port.nil?
+        errors << "winrm.guest_port cannot be nil."  if @guest_port.nil?
+        errors << "winrm.max_tries cannot be nil."   if @max_tries.nil?
+        errors << "winrm.retry_delay cannot be nil." if @max_tries.nil?
+        errors << "winrm.timeout cannot be nil."     if @timeout.nil?
         unless @ssl_peer_verification == true || @ssl_peer_verification == false
           errors << "winrm.ssl_peer_verification must be a boolean."
         end
diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index ae14e0f23..d9d5f28ce 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -88,7 +88,7 @@ module VagrantPlugins
       end
 
       def execute_shell_with_retry(command, shell, &block)
-        retryable(tries: @config.max_tries, on: @@exceptions_to_retry_on, sleep: 10) do
+        retryable(tries: @config.max_tries, on: @@exceptions_to_retry_on, sleep: @config.retry_delay) do
           @logger.debug("#{shell} executing:\n#{command}")
           output = session.send(shell, command) do |out, err|
             block.call(:stdout, out) if block_given? && out
@@ -124,7 +124,6 @@ module VagrantPlugins
               endpoint: endpoint,
               message: exception.message
         when WinRM::WinRMHTTPTransportError
-          case exception.status_code
           raise Errors::ExecutionError,
             shell: shell,
             command: command,
diff --git a/test/unit/plugins/communicators/winrm/shell_test.rb b/test/unit/plugins/communicators/winrm/shell_test.rb
index 22a50072d..de7b1dc19 100644
--- a/test/unit/plugins/communicators/winrm/shell_test.rb
+++ b/test/unit/plugins/communicators/winrm/shell_test.rb
@@ -12,6 +12,8 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
     VagrantPlugins::CommunicatorWinRM::Config.new.tap do |c|
       c.username = 'username'
       c.password = 'password'
+      c.max_tries = 3
+      c.retry_delay = 0
       c.finalize!
     end
   }
@@ -28,10 +30,13 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
       expect(subject.powershell("dir")[:exitcode]).to eq(0)
     end
 
-    it "should raise auth error when WinRM exception has a response code of 401" do
-      # The default settings might an account lockout - 20 auth failures!
-      expect(session).to receive(:powershell).with(/^dir.+/).exactly(20).times.and_raise(
-        WinRM::WinRMAuthorizationError.new("Oh no!!", 401))
+    it "should retry when a WinRMAuthorizationError is received" do
+      expect(session).to receive(:powershell).with(/^dir.+/).exactly(3).times.and_raise(
+        # Note: The initialize for WinRMAuthorizationError may require a status_code as
+        # the second argument in a future WinRM release. Currently it doesn't track the
+        # status code.
+        WinRM::WinRMAuthorizationError.new("Oh no!! Unauthrorized")
+      )
       expect { subject.powershell("dir") }.to raise_error(
         VagrantPlugins::CommunicatorWinRM::Errors::AuthenticationFailed)
     end