diff --git a/src/octoprint/server/__init__.py b/src/octoprint/server/__init__.py
index 115ed3f1..e5f45000 100644
--- a/src/octoprint/server/__init__.py
+++ b/src/octoprint/server/__init__.py
@@ -677,6 +677,11 @@ class Server():
 		assets = CustomDirectoryEnvironment(app)
 		assets.debug = not settings().getBoolean(["devel", "webassets", "bundle"])
 
+		UpdaterType = type(util.flask.SettingsCheckUpdater)(util.flask.SettingsCheckUpdater.__name__, (util.flask.SettingsCheckUpdater,), dict(
+			updater=assets.updater
+		))
+		assets.updater = UpdaterType
+
 		enable_gcodeviewer = settings().getBoolean(["gcodeViewer", "enabled"])
 		enable_timelapse = (settings().get(["webcam", "snapshot"]) and settings().get(["webcam", "ffmpeg"]))
 		preferred_stylesheet = settings().get(["devel", "stylesheet"])
diff --git a/src/octoprint/server/util/flask.py b/src/octoprint/server/util/flask.py
index 41d84e62..ebc3290a 100644
--- a/src/octoprint/server/util/flask.py
+++ b/src/octoprint/server/util/flask.py
@@ -11,6 +11,8 @@ import flask
 import flask.ext.login
 import flask.ext.principal
 import flask.ext.assets
+import webassets.updater
+import webassets.utils
 import functools
 import time
 import uuid
@@ -459,6 +461,46 @@ class PluginAssetResolver(flask.ext.assets.FlaskResolver):
 		import os
 		return os.path.normpath(os.path.join(ctx.environment.directory, target))
 
+##~~ Webassets updater that takes changes in the configuration into account
+
+class SettingsCheckUpdater(webassets.updater.BaseUpdater):
+
+	updater = "always"
+
+	def __init__(self):
+		self._delegate = webassets.updater.get_updater(self.__class__.updater)
+
+	def needs_rebuild(self, bundle, ctx):
+		return self._delegate.needs_rebuild(bundle, ctx) or self.changed_settings(ctx)
+
+	def changed_settings(self, ctx):
+		import json
+
+		if not ctx.cache:
+			return False
+
+		cache_key = ('octo', 'settings')
+		current_hash = webassets.utils.hash_func(json.dumps(settings().effective_yaml))
+		cached_hash = ctx.cache.get(cache_key)
+		# This may seem counter-intuitive, but if no cache entry is found
+		# then we actually return "no update needed". This is because
+		# otherwise if no cache / a dummy cache is used, then we would be
+		# rebuilding every single time.
+		if not cached_hash is None:
+			return cached_hash != current_hash
+		return False
+
+	def build_done(self, bundle, ctx):
+		import json
+
+		self._delegate.build_done(bundle, ctx)
+		if not ctx.cache:
+			return
+
+		cache_key = ('octo', 'settings')
+		cache_value = webassets.utils.hash_func(json.dumps(settings().effective_yaml))
+		ctx.cache.set(cache_key, cache_value)
+
 ##~~ plugin assets collector
 
 def collect_plugin_assets(enable_gcodeviewer=True, enable_timelapse=True, preferred_stylesheet="css"):
diff --git a/src/octoprint/settings.py b/src/octoprint/settings.py
index 80a78cad..74db8425 100644
--- a/src/octoprint/settings.py
+++ b/src/octoprint/settings.py
@@ -250,7 +250,7 @@ default_settings = {
 			"enabled": True
 		},
 		"webassets": {
-			"minify": True,
+			"minify": False,
 			"bundle": True
 		},
 		"virtualPrinter": {
@@ -415,7 +415,7 @@ class Settings(object):
 				if source is None:
 					raise TemplateNotFound(template)
 				mtime = self._settings._mtime
-				return source, None, lambda: mtime == self._settings._last_modified
+				return source, None, lambda: mtime == self._settings.last_modified
 
 			def list_templates(self):
 				scripts = self._settings.get(["scripts"], merged=True)
@@ -523,13 +523,23 @@ class Settings(object):
 
 		return map(process_control, controls)
 
+	@property
+	def effective(self):
+		import octoprint.util
+		return octoprint.util.dict_merge(default_settings, self._config)
+
+	@property
+	def effective_yaml(self):
+		import yaml
+		return yaml.safe_dump(self.effective)
+
 	#~~ load and save
 
 	def load(self, migrate=False):
 		if os.path.exists(self._configfile) and os.path.isfile(self._configfile):
 			with open(self._configfile, "r") as f:
 				self._config = yaml.safe_load(f)
-				self._mtime = self._last_modified
+				self._mtime = self.last_modified
 		# changed from else to handle cases where the file exists, but is empty / 0 bytes
 		if not self._config:
 			self._config = {}
@@ -768,7 +778,7 @@ class Settings(object):
 		return True
 
 	@property
-	def _last_modified(self):
+	def last_modified(self):
 		"""
 		Returns:
 		    int: The last modification time of the configuration file.
@@ -924,7 +934,7 @@ class Settings(object):
 		if len(path) == 0:
 			return
 
-		if self._mtime is not None and self._last_modified != self._mtime:
+		if self._mtime is not None and self.last_modified != self._mtime:
 			self.load()
 
 		config = self._config