diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index 1ae8b9047..deb241144 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -75,8 +75,7 @@ module VagrantPlugins
           ssh_auth_type = "password" if ssh_info[:password]
           @machine.ui.detail("SSH auth method: #{ssh_auth_type}")
 
-          last_message = nil
-          last_message_repeat_at = 0
+          previous_messages = {}
           while true
             message  = nil
             begin
@@ -123,14 +122,13 @@ module VagrantPlugins
             if message
               message_at   = Time.now.to_f
               show_message = true
-              if last_message == message
-                show_message = (message_at - last_message_repeat_at) > 10.0
+              if previous_messages[message]
+                show_message = (message_at - previous_messages[message]) > 10.0
               end
 
               if show_message
                 @machine.ui.detail("Warning: #{message} Retrying...")
-                last_message = message
-                last_message_repeat_at = message_at
+                previous_messages[message] = message_at
               end
             end
           end
diff --git a/test/unit/plugins/communicators/ssh/communicator_test.rb b/test/unit/plugins/communicators/ssh/communicator_test.rb
index a236c1931..cfbcad89b 100644
--- a/test/unit/plugins/communicators/ssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/ssh/communicator_test.rb
@@ -116,6 +116,49 @@ describe VagrantPlugins::CommunicatorSSH::Communicator do
           expect(communicator.wait_for_ready(0.6)).to eq(true)
         end
       end
+
+      context "when printing message to the user" do
+        before do
+          allow(machine).to receive(:ssh_info).
+            and_return(host: '10.1.2.3', port: 22).ordered
+          allow(communicator).to receive(:connect)
+          allow(communicator).to receive(:ready?).and_return(true)
+        end
+
+        it "should print message" do
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHConnectionTimeout)
+          expect(ui).to receive(:detail).with(/timeout/)
+          communicator.wait_for_ready(0.5)
+        end
+
+        it "should not print the same message twice" do
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHConnectionTimeout)
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHConnectionTimeout)
+          expect(ui).to receive(:detail).with(/timeout/)
+          expect(ui).not_to receive(:detail).with(/timeout/)
+          communicator.wait_for_ready(0.5)
+        end
+
+        it "should print different messages" do
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHConnectionTimeout)
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHDisconnected)
+          expect(ui).to receive(:detail).with(/timeout/)
+          expect(ui).to receive(:detail).with(/disconnect/)
+          communicator.wait_for_ready(0.5)
+        end
+
+        it "should not print different messages twice" do
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHConnectionTimeout)
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHDisconnected)
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHConnectionTimeout)
+          expect(communicator).to receive(:connect).and_raise(Vagrant::Errors::SSHDisconnected)
+          expect(ui).to receive(:detail).with(/timeout/)
+          expect(ui).to receive(:detail).with(/disconnect/)
+          expect(ui).not_to receive(:detail).with(/timeout/)
+          expect(ui).not_to receive(:detail).with(/disconnect/)
+          communicator.wait_for_ready(0.5)
+        end
+      end
     end
   end