diff --git a/plugins/communicators/winrm/helper.rb b/plugins/communicators/winrm/helper.rb
index b435a960c..03aff088c 100644
--- a/plugins/communicators/winrm/helper.rb
+++ b/plugins/communicators/winrm/helper.rb
@@ -33,10 +33,15 @@ module VagrantPlugins
         return addr if addr
 
         ssh_info = machine.ssh_info
-        raise Errors::WinRMNotReady if !ssh_info || ssh_info[:host].to_s.empty?
+        raise Errors::WinRMNotReady if winrm_info_invalid?(ssh_info)
         return ssh_info[:host]
       end
 
+      def self.winrm_info_invalid?(ssh_info)
+        invalid = (!ssh_info || ssh_info[:host].to_s.empty? || ssh_info[:host].to_s.match(/^169.254/))
+        return invalid
+      end
+
       # Returns the port to access WinRM.
       #
       # @param [Vagrant::Machine] machine
diff --git a/test/unit/plugins/communicators/winrm/helper_test.rb b/test/unit/plugins/communicators/winrm/helper_test.rb
index 80c7f8568..f030f7aa3 100644
--- a/test/unit/plugins/communicators/winrm/helper_test.rb
+++ b/test/unit/plugins/communicators/winrm/helper_test.rb
@@ -48,6 +48,12 @@ describe VagrantPlugins::CommunicatorWinRM::Helper do
       expect { subject.winrm_address(machine) }.
         to raise_error(VagrantPlugins::CommunicatorWinRM::Errors::WinRMNotReady)
     end
+
+    it "raise an exception if it detects an APIPA" do
+      machine.stub(ssh_info: { host: "169.254.123.123" })
+      expect { subject.winrm_address(machine) }.
+        to raise_error(VagrantPlugins::CommunicatorWinRM::Errors::WinRMNotReady)
+    end
   end
 
   describe ".winrm_info" do