diff --git a/src/WebCompiler/Config/Config.cs b/src/WebCompiler/Config/Config.cs
index a2a1d8e5..28388516 100644
--- a/src/WebCompiler/Config/Config.cs
+++ b/src/WebCompiler/Config/Config.cs
@@ -1,4 +1,5 @@
-using System.Collections.Generic;
+using System.Linq;
+using System.Collections.Generic;
 using System.IO;
 using Newtonsoft.Json;
 
@@ -27,6 +28,18 @@ public class Config
         [JsonProperty("inputFile")]
         public string InputFile { get; set; }
 
+        /// <summary>
+        /// The relative file path to the output files.
+        /// </summary>
+        [JsonProperty("outputFiles")]
+        public string OutputFiles { get; set; }
+
+        /// <summary>
+        /// The relative file path to the input files.
+        /// </summary>
+        [JsonProperty("inputFiles")]
+        public string InputFiles { get; set; }
+
         /// <summary>
         /// Settings for the minification.
         /// </summary>
@@ -58,8 +71,7 @@ public class Config
         /// </summary>
         public FileInfo GetAbsoluteInputFile()
         {
-            string folder = new FileInfo(FileName).DirectoryName;
-            return new FileInfo(Path.Combine(folder, InputFile.Replace("/", "\\")));
+            return new FileInfo(GetAbsolutePath(InputFile));
         }
 
         /// <summary>
@@ -67,8 +79,22 @@ public FileInfo GetAbsoluteInputFile()
         /// </summary>
         public FileInfo GetAbsoluteOutputFile()
         {
+            return new FileInfo(GetAbsolutePath(OutputFile));
+        }
+
+        private string GetAbsolutePath(string relativePath)
+        {
+            string folder = new FileInfo(FileName).DirectoryName;
+            return Path.Combine(folder, relativePath.Replace("/", "\\"));
+        }
+
+        private string GetRelativePath(string absolutePath)
+        {
+            if (absolutePath == null)
+                return null;
+
             string folder = new FileInfo(FileName).DirectoryName;
-            return new FileInfo(Path.Combine(folder, OutputFile.Replace("/", "\\")));
+            return absolutePath.Replace(folder, string.Empty).TrimStart('\\').Replace("\\", "/");
         }
 
         /// <summary>
@@ -85,6 +111,49 @@ internal bool CompilationRequired()
             return input.LastWriteTimeUtc > output.LastWriteTimeUtc;
         }
 
+        internal IEnumerable<Config> ExpandConfig()
+        {
+            string inputFiles = InputFiles;
+            string outputFiles = OutputFiles;
+
+            InputFiles = OutputFiles = null;
+
+            if (!string.IsNullOrEmpty(InputFile) && !string.IsNullOrEmpty(OutputFile))
+            {
+                yield return this;
+            }
+
+            if (string.IsNullOrEmpty(inputFiles) || string.IsNullOrEmpty(outputFiles))
+            {
+                yield break;
+            }
+
+            inputFiles = GetAbsolutePath(inputFiles);
+            outputFiles = GetAbsolutePath(outputFiles);
+
+            string inputFolder = Path.GetDirectoryName(inputFiles);
+            string inputFilePattern = Path.GetFileName(inputFiles);
+            string outputFolder = Path.GetDirectoryName(outputFiles);
+            string outputFilePattern = Path.GetFileName(outputFiles);
+
+            foreach (var filePath in Directory.GetFiles(inputFolder, inputFilePattern))
+            {
+                var fileConfig = Clone();
+                fileConfig.InputFile = GetRelativePath(filePath);
+                fileConfig.OutputFile = GetRelativePath(Path.Combine(outputFolder,
+                                                                        Path.ChangeExtension(Path.GetFileName(filePath), Path.GetExtension(outputFilePattern))));
+                yield return fileConfig;
+            }
+        }
+
+        private Config Clone()
+        {
+            var clone = (Config)MemberwiseClone();
+            clone.Minify = Minify.AsEnumerable().ToDictionary(kvp => kvp.Key, kvp => kvp.Value);
+            clone.Options = Options.AsEnumerable().ToDictionary(kvp => kvp.Key, kvp => kvp.Value);
+            return clone;
+        }
+
         /// <summary>
         /// Determines if the object is equals to the other object.
         /// </summary>
diff --git a/src/WebCompiler/Config/ConfigHandler.cs b/src/WebCompiler/Config/ConfigHandler.cs
index 260f06af..18185eef 100644
--- a/src/WebCompiler/Config/ConfigHandler.cs
+++ b/src/WebCompiler/Config/ConfigHandler.cs
@@ -18,7 +18,7 @@ public class ConfigHandler
         /// <param name="config">The compiler config object to add to the configration file.</param>
         public void AddConfig(string fileName, Config config)
         {
-            IEnumerable<Config> existing = GetConfigs(fileName);
+            IEnumerable<Config> existing = GetVerbatimConfigs(fileName);
             List<Config> configs = new List<Config>();
             configs.AddRange(existing);
             configs.Add(config);
@@ -39,7 +39,7 @@ public void AddConfig(string fileName, Config config)
         /// </summary>
         public void RemoveConfig(Config configToRemove)
         {
-            IEnumerable<Config> configs = GetConfigs(configToRemove.FileName);
+            IEnumerable<Config> configs = GetVerbatimConfigs(configToRemove.FileName);
             List<Config> newConfigs = new List<Config>();
 
             if (configs.Contains(configToRemove))
@@ -95,6 +95,16 @@ public void CreateDefaultsFile(string fileName)
         /// <param name="fileName">A relative or absolute file path to the configuration file.</param>
         /// <returns>A list of Config objects.</returns>
         public static IEnumerable<Config> GetConfigs(string fileName)
+        {
+            IEnumerable<Config> configs = GetVerbatimConfigs(fileName);
+
+            if (configs != null && configs.Any())
+                configs = configs.SelectMany(c => c.ExpandConfig()).Distinct().ToList();
+
+            return configs;
+        }
+
+        private static IEnumerable<Config> GetVerbatimConfigs(string fileName)
         {
             FileInfo file = new FileInfo(fileName);
 
diff --git a/src/WebCompilerTest/Config/ConfigHandlerTest.cs b/src/WebCompilerTest/Config/ConfigHandlerTest.cs
index 700d80f1..23769ca2 100644
--- a/src/WebCompilerTest/Config/ConfigHandlerTest.cs
+++ b/src/WebCompilerTest/Config/ConfigHandlerTest.cs
@@ -35,6 +35,8 @@ public void AddConfig()
             var newConfig = new WebCompiler.Config();
             const string newInputFileName = "newInputFile";
             newConfig.InputFile = newInputFileName;
+            const string newOutputFileName = "newOutputFile";
+            newConfig.OutputFile = newOutputFileName;
 
             _handler.AddConfig(processingConfigFile, newConfig);
 
diff --git a/src/WebCompilerVsix/JSON/compilerconfig-schema.json b/src/WebCompilerVsix/JSON/compilerconfig-schema.json
index 7b42f8e6..578f280f 100644
--- a/src/WebCompilerVsix/JSON/compilerconfig-schema.json
+++ b/src/WebCompilerVsix/JSON/compilerconfig-schema.json
@@ -87,24 +87,24 @@
     },
 
     "config": {
-      "required": [ "outputFile", "inputFile" ],
-
-      "properties": {
+        "properties": {
         "includeInProject": {
           "description": "Set to true to include the output file in the project. Doesn't work in some Visual Studio project types like ASP.NET 5 applications.",
           "type": "boolean",
           "default": true
         },
+        "inputFiles": { "type": "string" },
         "inputFile": {
-          "description": "One or more relative file names to bundle.",
-          "type": "string",
-          "format": "compiler_relativepath"
+            "description": "One or more relative file names to bundle.",
+            "type": "string",
+            "format": "compiler_relativepath"
         },
         "minify": {
-          "description": "Specify options for minification of the output file.",
-          "type": "object",
-          "allOf": [ { "$ref": "compilerdefaults-schema.json#/definitions/baseMinify" } ]
+            "description": "Specify options for minification of the output file.",
+            "type": "object",
+            "allOf": [ { "$ref": "compilerdefaults-schema.json#/definitions/baseMinify" } ]
         },
+        "outputFiles": { "type": "string" },
         "outputFile": {
           "description": "The relative path to the desired output file name.",
           "type": "string",