diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index 56525a40b..3d3d5a4b8 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -196,8 +196,13 @@ module VagrantPlugins
 
           # Adjust private key file permissions
           if Vagrant::Util::Platform.windows?
-            priv_path = @machine.data_dir.join("private_key").to_s
-            File.set_permissions(priv_path, Etc.getlogin => File::FULL)
+            begin
+              priv_path = @machine.data_dir.join("private_key").to_s
+              File.set_permissions(priv_path, Etc.getlogin => File::FULL)
+            rescue => e
+              @logger.warn("Error encountered during private key permissions set - " \
+                "#{e.class}: #{e.message}")
+            end
           else
             @machine.data_dir.join("private_key").chmod(0600)
           end
diff --git a/test/unit/plugins/communicators/ssh/communicator_test.rb b/test/unit/plugins/communicators/ssh/communicator_test.rb
index 8f8f88806..1b244b8a3 100644
--- a/test/unit/plugins/communicators/ssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/ssh/communicator_test.rb
@@ -231,6 +231,10 @@ describe VagrantPlugins::CommunicatorSSH::Communicator do
             expect(File).to receive(:set_permissions).with("PRIVATE_KEY_PATH", any_args)
           end
 
+          it "should proceed when error is encountered" do
+            expect(File).to receive(:set_permissions).and_raise(StandardError)
+          end
+
           context "with multiple permissions on file" do
 
             it "should delete all non-owner permissions" do