diff --git a/src/MICore/LaunchOptions.cs b/src/MICore/LaunchOptions.cs
index 7c102711f..95f1ee049 100644
--- a/src/MICore/LaunchOptions.cs
+++ b/src/MICore/LaunchOptions.cs
@@ -370,7 +370,7 @@ public static ReadOnlyCollection<SourceMapEntry> CreateCollection(Xml.LaunchOpti
 
         public static ReadOnlyCollection<SourceMapEntry> CreateCollection(Dictionary<string, object> source)
         {
-            IList<SourceMapEntry> sourceMaps = new List<SourceMapEntry>(source.Keys.Count);
+            var sourceMaps = new List<SourceMapEntry>(source.Keys.Count);
 
             foreach (var item in source)
             {
@@ -416,6 +416,11 @@ public static ReadOnlyCollection<SourceMapEntry> CreateCollection(Dictionary<str
                     throw new InvalidLaunchOptionsException(String.Format(CultureInfo.CurrentCulture, MICoreResources.Error_SourceFileMapInvalidEditorPath));
                 }
             }
+
+            // Ensure the map is sorted such that more specific directories are in front of less specific by sorting the map
+            // in descending order of the compile time path
+            sourceMaps.Sort((x, y) => string.CompareOrdinal(y.CompileTimePath, x.CompileTimePath));
+            
             return new ReadOnlyCollection<SourceMapEntry>(sourceMaps);
         }
     }