diff --git a/plugins/OptionalManager/OptionalManagerPlugin.py b/plugins/OptionalManager/OptionalManagerPlugin.py
index 53e58353..b2b68dd4 100644
--- a/plugins/OptionalManager/OptionalManagerPlugin.py
+++ b/plugins/OptionalManager/OptionalManagerPlugin.py
@@ -53,6 +53,10 @@ if "access_log" not in locals().keys():  # To keep between module reloads
 
 @PluginManager.registerTo("ContentManager")
 class ContentManagerPlugin(object):
+    def __init__(self, *args, **kwargs):
+        self.cache_is_pinned = {}
+        super(ContentManagerPlugin, self).__init__(*args, **kwargs)
+
     def optionalDownloaded(self, inner_path, hash_id, size=None, own=False):
         if "|" in inner_path:  # Big file piece
             file_inner_path, file_range = inner_path.split("|")
@@ -100,6 +104,14 @@ class ContentManagerPlugin(object):
             return False
 
 
+    def optionalDelete(self, inner_path):
+        if self.isPinned(inner_path):
+            self.site.log.debug("Skip deleting pinned optional file: %s" % inner_path)
+            return False
+        else:
+            return super(ContentManagerPlugin, self).optionalDelete(inner_path)
+
+
 @PluginManager.registerTo("WorkerManager")
 class WorkerManagerPlugin(object):
     def doneTask(self, task):
diff --git a/src/Content/ContentManager.py b/src/Content/ContentManager.py
index feecca28..1367bc39 100644
--- a/src/Content/ContentManager.py
+++ b/src/Content/ContentManager.py
@@ -113,10 +113,10 @@ class ContentManager(object):
                         try:
                             old_hash_id = self.hashfield.getHashId(old_hash)
                             self.optionalRemoved(file_inner_path, old_hash_id, old_content["files_optional"][relative_path]["size"])
-                            self.site.storage.delete(file_inner_path)
+                            self.optionalDelete(file_inner_path)
                             self.log.debug("Deleted changed optional file: %s" % file_inner_path)
                         except Exception, err:
-                            self.log.debug("Error deleting file %s: %s" % (file_inner_path, err))
+                            self.log.debug("Error deleting file %s: %s" % (file_inner_path, Debug.formatException(err)))
                 else:  # The file is not in the old content
                     if self.site.isDownloadable(file_inner_path):
                         changed.append(file_inner_path)  # Download new file
@@ -143,14 +143,17 @@ class ContentManager(object):
 
                             # Check if the deleted file is optional
                             if old_content.get("files_optional") and old_content["files_optional"].get(file_relative_path):
+                                self.optionalDelete(file_inner_path)
                                 old_hash = old_content["files_optional"][file_relative_path].get("sha512")
                                 if self.hashfield.hasHash(old_hash):
                                     old_hash_id = self.hashField.getHashid(old_hash)
                                     self.optionalRemoved(file_inner_path, old_hash_id, old_content["files_optional"][file_relative_path]["size"])
+                            else:
+                                self.site.storage.delete(file_inner_path)
 
                             self.log.debug("Deleted file: %s" % file_inner_path)
                         except Exception, err:
-                            self.log.debug("Error deleting file %s: %s" % (file_inner_path, err))
+                            self.log.debug("Error deleting file %s: %s" % (file_inner_path, Debug.formatException(err)))
 
                     # Cleanup empty dirs
                     tree = {root: [dirs, files] for root, dirs, files in os.walk(self.site.storage.getPath(content_inner_dir))}
@@ -950,6 +953,9 @@ class ContentManager(object):
             else:  # File not in content.json
                 raise VerifyError("File not in content.json")
 
+    def optionalDelete(self, inner_path):
+        self.site.storage.delete(inner_path)
+
     def optionalDownloaded(self, inner_path, hash_id, size=None, own=False):
         if size is None:
             size = self.site.storage.getSize(inner_path)