diff --git a/src/octoprint/server/__init__.py b/src/octoprint/server/__init__.py
index 2c9e39e1..21fc5698 100644
--- a/src/octoprint/server/__init__.py
+++ b/src/octoprint/server/__init__.py
@@ -663,15 +663,18 @@ class Server():
 		# we clean up entries from our preemptive cache settings that haven't been
 		# accessed longer than server.preemptiveCache.until days
 		preemptive_cache_timeout = settings().getInt(["server", "preemptiveCache", "until"])
-		cutoff_timestamp = time.time() + preemptive_cache_timeout * 24 * 60 * 60
+		cutoff_timestamp = time.time() - preemptive_cache_timeout * 24 * 60 * 60
 
-		cache_data = preemptive_cache.clean_all_data(lambda root, entries: filter(lambda entry: "_timestamp" in entry and entry["_timestamp"] <= cutoff_timestamp, entries))
+		def filter_old_entries(entry):
+			return "_timestamp" in entry and entry["_timestamp"] > cutoff_timestamp
+
+		cache_data = preemptive_cache.clean_all_data(lambda root, entries: filter(filter_old_entries, entries))
 		if not cache_data:
 			return
 
 		def execute_caching():
 			for route in sorted(cache_data.keys(), key=lambda x: (x.count("/"), x)):
-				entries = cache_data[route]
+				entries = reversed(sorted(cache_data[route], key=lambda x: x.get("_count", 0)))
 				for kwargs in entries:
 					plugin = kwargs.get("plugin", None)
 					additional_request_data = kwargs.get("_additional_request_data", dict())
@@ -683,7 +686,7 @@ class Server():
 						else:
 							self._logger.info("Preemptively caching {} for {!r}".format(route, kwargs))
 						builder = EnvironBuilder(**kwargs)
-						with preemptive_cache.disable_timestamp_update():
+						with preemptive_cache.disable_access_logging():
 							app(builder.get_environ(), lambda *a, **kw: None)
 					except:
 						self._logger.exception("Error while trying to preemptively cache {} for {!r}".format(route, kwargs))
diff --git a/src/octoprint/server/util/flask.py b/src/octoprint/server/util/flask.py
index 0ba64d4b..57a53cf7 100644
--- a/src/octoprint/server/util/flask.py
+++ b/src/octoprint/server/util/flask.py
@@ -386,7 +386,7 @@ class PreemptiveCache(object):
 
 		self._lock = threading.RLock()
 		self._logger = logging.getLogger(__name__ + "." + self.__class__.__name__)
-		self._update_timestamp = True
+		self._log_access = True
 
 	def record(self, data, unless=None):
 		if callable(unless) and unless():
@@ -401,11 +401,11 @@ class PreemptiveCache(object):
 			self.add_data(request.path, entry_data)
 
 	@contextlib.contextmanager
-	def disable_timestamp_update(self):
+	def disable_access_logging(self):
 		with self._lock:
-			self._update_timestamp = False
+			self._log_access = False
 			yield
-			self._update_timestamp = True
+			self._log_access = True
 
 	def clean_all_data(self, cleanup_function):
 		assert callable(cleanup_function)
@@ -507,12 +507,14 @@ class PreemptiveCache(object):
 				import copy
 				to_persist = copy.deepcopy(data)
 				to_persist["_timestamp"] = time.time()
+				to_persist["_count"] = 1
 				self._logger.info("Adding entry for {} and {!r}".format(root, to_persist))
-			elif self._update_timestamp:
+			elif self._log_access:
 				to_persist["_timestamp"] = time.time()
-				self._logger.debug("Updating timestamp for {} and {!r}".format(root, data))
+				to_persist["_count"] = to_persist.get("_count", 0) + 1
+				self._logger.debug("Updating timestamp and counter for {} and {!r}".format(root, data))
 			else:
-				self._logger.debug("Not updating timestamp for {} and {!r}, currently flagged as disabled".format(root, data))
+				self._logger.debug("Not updating timestamp and counter for {} and {!r}, currently flagged as disabled".format(root, data))
 
 			self.set_data(root, [to_persist] + other)