diff --git a/src/main/java/io/airlift/airline/ParseOptionConversionException.java b/src/main/java/io/airlift/airline/ParseOptionConversionException.java
index b83ab1cfe..34baabce1 100644
--- a/src/main/java/io/airlift/airline/ParseOptionConversionException.java
+++ b/src/main/java/io/airlift/airline/ParseOptionConversionException.java
@@ -24,14 +24,19 @@ public class ParseOptionConversionException extends ParseException
     private final String value;
     private final String typeName;
 
-    ParseOptionConversionException(String optionTitle, String value, String typeName)
+    ParseOptionConversionException(String optionTitle, String value, String typeName, String additionalComment)
     {
-        super("%s: can not convert \"%s\" to a %s", optionTitle, value, typeName);
+        super("%s: can not convert \"%s\" to a %s. %s", optionTitle, value, typeName, additionalComment);
         this.optionTitle = optionTitle;
         this.value = value;
         this.typeName = typeName;
     }
 
+    ParseOptionConversionException(String optionTitle, String value, String typeName)
+    {
+        this(optionTitle, value, typeName, "");
+    }
+
     public String getOptionTitle()
     {
         return optionTitle;
diff --git a/src/main/java/io/airlift/airline/TypeConverter.java b/src/main/java/io/airlift/airline/TypeConverter.java
index ae4543f40..9aadc9b81 100644
--- a/src/main/java/io/airlift/airline/TypeConverter.java
+++ b/src/main/java/io/airlift/airline/TypeConverter.java
@@ -1,9 +1,15 @@
 package io.airlift.airline;
 
+import com.google.common.base.Function;
+import com.google.common.base.Joiner;
 import com.google.common.base.Preconditions;
+import com.google.common.collect.Lists;
 
 import java.lang.reflect.Constructor;
+import java.lang.reflect.InvocationTargetException;
 import java.lang.reflect.Method;
+import java.util.Arrays;
+import java.util.List;
 
 public class TypeConverter
 {
@@ -53,16 +59,35 @@ else if (Double.class.isAssignableFrom(type) || Double.TYPE.isAssignableFrom(typ
             if (valueOf.getReturnType().isAssignableFrom(type)) {
                 return valueOf.invoke(null, value);
             }
-        } catch (Throwable ignored) {
+        }
+        catch (Throwable ignored) {
         }
 
         // Look for a static valueOf(String) method (this covers enums which have a valueOf method)
         try {
             Method valueOf = type.getMethod("valueOf", String.class);
             if (valueOf.getReturnType().isAssignableFrom(type)) {
-                return valueOf.invoke(null, value);
+                try {
+                    return valueOf.invoke(null, value);
+                }
+                catch (InvocationTargetException e) {
+                    if (type.isEnum()) {
+                        List<String> enumConstantNames = Lists.transform(Arrays.asList(((Class<Enum>) type).getEnumConstants()), new Function<Enum, String>() {
+                            @Override
+                            public String apply(Enum input)
+                            {
+                                return input.name();
+                            }
+                        });
+                        String message = String.format("Invalid %s, Valid values are: %s", name, Joiner.on(", ").join(enumConstantNames));
+                        throw new ParseOptionConversionException(name, value, type.getSimpleName(), message);
+                    }
+                }
             }
         }
+        catch (ParseOptionConversionException e) {
+            throw e;
+        }
         catch (Throwable ignored) {
         }