diff --git a/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs b/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs
index 10730a9543..29c8fb2e13 100644
--- a/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs
+++ b/src/chocolatey.tests/infrastructure/commandline/InteractivePromptSpecs.cs
@@ -495,17 +495,42 @@ public void should_error_when_the_prompt_input_is_null()
                 choices = new List<string> { "bob" };
                 prompt_value = null;
                 bool errored = false;
+                string errorMessage = string.Empty;
                 console.Setup(c => c.ReadLine()).Returns(""); //Enter pressed
                 try
                 {
                     prompt();
                 }
-                catch (Exception)
+                catch (Exception ex)
                 {
                     errored = true;
+                    errorMessage = ex.Message;
+                }
+
+                errored.ShouldBeTrue();
+                errorMessage.ShouldContain("Value for prompt cannot be null.");
+                console.Verify(c => c.ReadLine(), Times.Never);
+            }
+
+            [Fact]
+            public void should_error_when_the_choicelist_contains_empty_values()
+            {
+                choices = new List<string> { "bob", "" };
+                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("Some choices are empty.");
                 console.Verify(c => c.ReadLine(), Times.Never);
             }
 
@@ -527,7 +552,7 @@ public void should_error_when_the_choicelist_has_multiple_items_with_same_first_
                 }
 
                 errored.ShouldBeTrue();
-                errorMessage.ShouldContain("Multiple choices have the same first letter. Please ensure you pass choices with different first letters.");
+                errorMessage.ShouldContain("Multiple choices have the same first letter.");
                 console.Verify(c => c.ReadLine(), Times.Never);
             }
         }
diff --git a/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs b/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs
index ddb3688baf..33a05dab35 100644
--- a/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs
+++ b/src/chocolatey/infrastructure/commandline/InteractivePrompt.cs
@@ -49,6 +49,11 @@ public static string prompt_for_confirmation_short(string prompt, IEnumerable<st
                 .meets(
                     c => c.Any(),
                     (name, value) => { throw new ApplicationException("No choices passed in. Please ensure you pass choices."); });
+            Ensure
+                .that(() => choices)
+                .meets(
+                    c => !c.Any(String.IsNullOrWhiteSpace),
+                    (name, value) => { throw new ApplicationException("Some choices are empty. Please ensure you provide no empty choices."); });
             Ensure
                 .that(() => choices)
                 .meets(
@@ -65,7 +70,7 @@ public static string prompt_for_confirmation_short(string prompt, IEnumerable<st
             // 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))
+                if (choice.is_equal_to(selection) || choice.Substring(0, 1).is_equal_to(selection))
                 {
                     selection = choice;
                     return selection;