diff --git a/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs b/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs
index 0b3c4eaf66..10730a9543 100644
--- a/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs
+++ b/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs
@@ -437,5 +437,183 @@ public void should_error_when_any_choice_not_available_is_given()
                 console.Verify(c => c.ReadLine(), Times.AtLeast(8));
             }
         }
+
+        public class when_prompting_short_with_interactivePrompt_guard_errors : InteractivePromptSpecsBase
+        {
+            private Func<string> prompt;
+
+            public override void Because()
+            {
+                console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
+                prompt = () => InteractivePrompt.prompt_for_confirmation_short(prompt_value, choices);
+            }
+
+            [Fact]
+            public void should_error_when_the_choicelist_is_null()
+            {
+                choices = null;
+                bool errored = false;
+                console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
+                try
+                {
+                    prompt();
+                }
+                catch (Exception)
+                {
+                    errored = true;
+                }
+
+                errored.ShouldBeTrue();
+                console.Verify(c => c.ReadLine(), Times.Never);
+            }
+
+            [Fact]
+            public void should_error_when_the_choicelist_is_empty()
+            {
+                choices = new List<string>();
+                bool errored = false;
+                string errorMessage = string.Empty;
+                console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
+                try
+                {
+                    prompt();
+                }
+                catch (Exception ex)
+                {
+                    errored = true;
+                    errorMessage = ex.Message;
+                }
+
+                errored.ShouldBeTrue();
+                errorMessage.ShouldContain("No choices passed in.");
+                console.Verify(c => c.ReadLine(), Times.Never);
+            }
+
+            [Fact]
+            public void should_error_when_the_prompt_input_is_null()
+            {
+                choices = new List<string> { "bob" };
+                prompt_value = null;
+                bool errored = false;
+                console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
+                try
+                {
+                    prompt();
+                }
+                catch (Exception)
+                {
+                    errored = true;
+                }
+
+                errored.ShouldBeTrue();
+                console.Verify(c => c.ReadLine(), Times.Never);
+            }
+
+            [Fact]
+            public void should_error_when_the_choicelist_has_multiple_items_with_same_first_letter()
+            {
+                choices = new List<string> {"sally", "suzy"};
+                bool errored = false;
+                string errorMessage = string.Empty;
+                console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
+                try
+                {
+                    prompt();
+                }
+                catch (Exception ex)
+                {
+                    errored = true;
+                    errorMessage = ex.Message;
+                }
+
+                errored.ShouldBeTrue();
+                errorMessage.ShouldContain("Multiple choices have the same first letter. Please ensure you pass choices with different first letters.");
+                console.Verify(c => c.ReadLine(), Times.Never);
+            }
+        }
+
+        public class when_prompting_short_with_interactivePrompt : InteractivePromptSpecsBase
+        {
+            private Func<string> prompt;
+
+            public override void Because()
+            {
+                prompt = () => InteractivePrompt.prompt_for_confirmation_short(prompt_value, choices);
+            }
+
+            public override void AfterObservations()
+            {
+                base.AfterObservations();
+                should_have_called_Console_ReadLine();
+            }
+
+            [Fact]
+            public void should_error_when_no_answer_given()
+            {
+                bool errored = false;
+
+                console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
+                try
+                {
+                    prompt();
+                }
+                catch (Exception)
+                {
+                    errored = true;
+                }
+                errored.ShouldBeTrue();
+                console.Verify(c => c.ReadLine(), Times.AtLeast(8));
+            }
+
+            [Fact]
+            public void should_return_yes_when_yes_is_given()
+            {
+                console.Setup(c => c.ReadLine()).Returns("yes");
+                var result = prompt();
+                result.ShouldEqual("yes");
+            }
+
+            [Fact]
+            public void should_return_yes_when_y_is_given()
+            {
+                console.Setup(c => c.ReadLine()).Returns("y");
+                var result = prompt();
+                result.ShouldEqual("yes");
+            }
+
+            [Fact]
+            public void should_return_no_choice_when_no_is_given()
+            {
+                console.Setup(c => c.ReadLine()).Returns("no");
+                var result = prompt();
+                result.ShouldEqual("no");
+            }
+
+            [Fact]
+            public void should_return_no_choice_when_n_is_given()
+            {
+                console.Setup(c => c.ReadLine()).Returns("n");
+                var result = prompt();
+                result.ShouldEqual("no");
+            }
+
+            [Fact]
+            public void should_error_when_any_choice_not_available_is_given()
+            {
+                bool errored = false;
+
+                console.Setup(c => c.ReadLine()).Returns("yup"); //Enter pressed
+                try
+                {
+                    prompt();
+                }
+                catch (Exception)
+                {
+                    errored = true;
+                }
+                errored.ShouldBeTrue();
+                console.Verify(c => c.ReadLine(), Times.AtLeast(8));
+            }
+        }
     }
 }
\ No newline at end of file
diff --git a/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs b/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs
index 4f5eed890b..a8b2394944 100644
--- a/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs
+++ b/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs
@@ -39,6 +39,40 @@ private static IConsole Console
             get { return _console.Value; }
         }
 
+        public static string prompt_for_confirmation_short(string prompt, IEnumerable<string> choices, int repeat = 10)
+        {
+            if (repeat < 0) throw new ApplicationException("Too many bad attempts. Stopping before application crash.");
+            Ensure.that(() => prompt).is_not_null();
+            Ensure.that(() => choices).is_not_null();
+            Ensure
+                .that(() => choices)
+                .meets(
+                    c => c.Any(),
+                    (name, value) => { throw new ApplicationException("No choices passed in. Please ensure you pass choices."); });
+            Ensure
+                .that(() => choices)
+                .meets(
+                    c => c.Select(entry => entry.FirstOrDefault()).Distinct().Count() == c.Count(),
+                    (name, value) => { throw new ApplicationException("Multiple choices have the same first letter. Please ensure you pass choices with different first letters."); });
+
+            "chocolatey".Log().Info(ChocolateyLoggers.Important, "{0} ({1}): ".format_with(prompt, String.Join("/", choices)));
+
+            var selection = Console.ReadLine();
+
+            // check to see if value was passed
+            foreach (var choice in choices)
+            {
+                if (choice.is_equal_to(selection) || choice.FirstOrDefault().ToString().is_equal_to(selection))
+                {
+                    selection = choice;
+                    return selection;
+                }
+            }
+
+            "chocolatey".Log().Error(ChocolateyLoggers.Important, "Your choice of '{0}' is not a valid selection.".format_with(selection));
+            return prompt_for_confirmation_short(prompt, choices, repeat - 1);
+        }
+
         public static string prompt_for_confirmation(string prompt, IEnumerable<string> choices, string defaultChoice, bool requireAnswer, int repeat = 10)
         {
             if (repeat < 0) throw new ApplicationException("Too many bad attempts. Stopping before application crash.");