diff --git a/common/lib/xmodule/xmodule/static_content.py b/common/lib/xmodule/xmodule/static_content.py
index 2c1622111c66..aecd2091fec2 100755
--- a/common/lib/xmodule/xmodule/static_content.py
+++ b/common/lib/xmodule/xmodule/static_content.py
@@ -74,7 +74,7 @@ class VideoBlock(HTMLSnippet):
 
 def write_module_styles(output_root):
     """Write all registered XModule css, sass, and scss files to output root."""
-    return _write_styles('.xmodule_display', output_root, sorted(_list_modules(), key=str), 'get_preview_view_css')
+    return _write_styles('.xmodule_display', output_root, _list_modules(), 'get_preview_view_css')
 
 
 def write_module_js(output_root):
@@ -94,20 +94,26 @@ def write_descriptor_js(output_root):
 
 def _list_descriptors():
     """Return a list of all registered XModuleDescriptor classes."""
-    return [
-        desc for desc in [
-            desc for (_, desc) in XModuleDescriptor.load_classes()
-        ]
-    ] + XBLOCK_CLASSES
+    return sorted(
+        [
+            desc for desc in [
+                desc for (_, desc) in XModuleDescriptor.load_classes()
+            ]
+        ] + XBLOCK_CLASSES,
+        key=str
+    )
 
 
 def _list_modules():
     """Return a list of all registered XModule classes."""
-    return [
-        desc.module_class for desc in [
-            desc for (_, desc) in XModuleDescriptor.load_classes()
-        ]
-    ] + XBLOCK_CLASSES
+    return sorted(
+        [
+            desc.module_class for desc in [
+                desc for (_, desc) in XModuleDescriptor.load_classes()
+            ]
+        ] + XBLOCK_CLASSES,
+        key=str
+    )
 
 
 def _ensure_dir(directory):
@@ -269,7 +275,13 @@ def write_webpack(output_file, module_files, descriptor_files):
         outfile.write(
             textwrap.dedent(u"""\
                 module.exports = {config_json};
-            """).format(config_json=json.dumps(config, indent=4))
+            """).format(
+                config_json=json.dumps(
+                    config,
+                    indent=4,
+                    sort_keys=True
+                )
+            )
         )
 
 
diff --git a/package-lock.json b/package-lock.json
index 6814471a9fca..c7485c3b51f1 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -2522,6 +2522,11 @@
       "integrity": "sha1-lCg191Dk7GGjCOYMLvjMEBEgLvw=",
       "dev": true
     },
+    "charenc": {
+      "version": "0.0.2",
+      "resolved": "https://registry.npmjs.org/charenc/-/charenc-0.0.2.tgz",
+      "integrity": "sha1-wKHS86cJLgN3S/qD8UwPxXkKhmc="
+    },
     "cheerio": {
       "version": "1.0.0-rc.2",
       "resolved": "https://registry.npmjs.org/cheerio/-/cheerio-1.0.0-rc.2.tgz",
@@ -3070,6 +3075,11 @@
         "which": "^1.2.9"
       }
     },
+    "crypt": {
+      "version": "0.0.2",
+      "resolved": "https://registry.npmjs.org/crypt/-/crypt-0.0.2.tgz",
+      "integrity": "sha1-iNf/fsDfuG9xPch7u0LQRNPmxBs="
+    },
     "crypto-browserify": {
       "version": "3.12.0",
       "resolved": "https://registry.npmjs.org/crypto-browserify/-/crypto-browserify-3.12.0.tgz",
@@ -9038,6 +9048,16 @@
       "integrity": "sha1-zrnatkWPSpVW3DbpHa9+y/6urHY=",
       "dev": true
     },
+    "md5": {
+      "version": "2.3.0",
+      "resolved": "https://registry.npmjs.org/md5/-/md5-2.3.0.tgz",
+      "integrity": "sha512-T1GITYmFaKuO91vxyoQMFETst+O71VUPEU3ze5GNzDm0OWdP8v1ziTaAEPUr/3kLsY3Sftgz242A1SetQiDL7g==",
+      "requires": {
+        "charenc": "0.0.2",
+        "crypt": "0.0.2",
+        "is-buffer": "~1.1.6"
+      }
+    },
     "md5.js": {
       "version": "1.3.4",
       "resolved": "https://registry.npmjs.org/md5.js/-/md5.js-1.3.4.tgz",
@@ -10901,7 +10921,7 @@
     "private": {
       "version": "0.1.8",
       "resolved": "https://registry.npmjs.org/private/-/private-0.1.8.tgz",
-      "integrity": "sha1-I4Hts2ifelPWUxkAYPz4ItLzaP8="
+      "integrity": "sha512-VvivMrbvd2nKkiG38qjULzlc+4Vx4wm/whI9pQD35YrARNnhxeiRktSOhSukRLFNlzg6Br/cJPet5J/u19r/mg=="
     },
     "process": {
       "version": "0.11.10",
@@ -15419,6 +15439,14 @@
         }
       }
     },
+    "webpack-md5-hash": {
+      "version": "0.0.6",
+      "resolved": "https://registry.npmjs.org/webpack-md5-hash/-/webpack-md5-hash-0.0.6.tgz",
+      "integrity": "sha512-HrQ0AJpeXHRa3IjsgyyEfTx8EqYs5y/4x/WklSYsNDcqBixHzCkrmJV5U+4ks+sx7ycKoIdqWLdyuk913FCS+Q==",
+      "requires": {
+        "md5": "^2.0.0"
+      }
+    },
     "webpack-merge": {
       "version": "4.1.1",
       "resolved": "https://registry.npmjs.org/webpack-merge/-/webpack-merge-4.1.1.tgz",
diff --git a/package.json b/package.json
index 527c68b1aa5f..a9a60ff72312 100644
--- a/package.json
+++ b/package.json
@@ -63,6 +63,7 @@
     "underscore.string": "3.3.5",
     "webpack": "2.7.0",
     "webpack-bundle-tracker": "0.2.1",
+    "webpack-md5-hash": "0.0.6",
     "webpack-merge": "4.1.1",
     "whatwg-fetch": "2.0.3",
     "which-country": "1.0.0"
diff --git a/webpack.prod.config.js b/webpack.prod.config.js
index 360ab56d4d01..5e32fa10e316 100644
--- a/webpack.prod.config.js
+++ b/webpack.prod.config.js
@@ -5,6 +5,7 @@
 var Merge = require('webpack-merge');
 var webpack = require('webpack');
 var BundleTracker = require('webpack-bundle-tracker');
+var WebpackMd5Hash = require("webpack-md5-hash");
 var _ = require('underscore');
 
 var commonConfig = require('./webpack.common.config.js');
@@ -29,7 +30,8 @@ var optimizedConfig = Merge.smart(commonConfig, {
             name: 'commons',
             filename: 'commons.[chunkhash].js',
             minChunks: 3
-        })
+        }),
+        new WebpackMd5Hash()
     ]
 }});