diff --git a/src/Config.py b/src/Config.py
index 420343f5..c54fdf00 100644
--- a/src/Config.py
+++ b/src/Config.py
@@ -106,6 +106,7 @@ class Config(object):
         action.add_argument('privatekey', help='Private key (default: ask on execute)', nargs='?')
         action.add_argument('--inner_path', help='File you want to sign (default: content.json)',
                             default="content.json", metavar="inner_path")
+        action.add_argument('--remove_missing_optional', help='Remove optional files that is not present in the directory', action='store_true')
         action.add_argument('--publish', help='Publish site after the signing', action='store_true')
 
         # SitePublish
diff --git a/src/Content/ContentManager.py b/src/Content/ContentManager.py
index 018bda2c..f13b3e2d 100644
--- a/src/Content/ContentManager.py
+++ b/src/Content/ContentManager.py
@@ -491,7 +491,7 @@ class ContentManager(object):
 
     # Create and sign a content.json
     # Return: The new content if filewrite = False
-    def sign(self, inner_path="content.json", privatekey=None, filewrite=True, update_changed_files=False, extend=None):
+    def sign(self, inner_path="content.json", privatekey=None, filewrite=True, update_changed_files=False, extend=None, remove_missing_optional=False):
         if inner_path in self.contents:
             content = self.contents[inner_path]
             if self.contents[inner_path].get("cert_sign", False) is None and self.site.storage.isFile(inner_path):
@@ -523,6 +523,11 @@ class ContentManager(object):
             helper.getDirname(inner_path), content.get("ignore"), content.get("optional")
         )
 
+        if not remove_missing_optional:
+            for file_inner_path, file_details in content.get("files_optional", {}).iteritems():
+                if file_inner_path not in files_optional_node:
+                    files_optional_node[file_inner_path] = file_details
+
         # Find changed files
         files_merged = files_node.copy()
         files_merged.update(files_optional_node)
diff --git a/src/Ui/UiWebsocket.py b/src/Ui/UiWebsocket.py
index 9336d7d3..6de470dd 100644
--- a/src/Ui/UiWebsocket.py
+++ b/src/Ui/UiWebsocket.py
@@ -287,7 +287,7 @@ class UiWebsocket(object):
         self.response(to, ret)
 
     # Sign content.json
-    def actionSiteSign(self, to, privatekey=None, inner_path="content.json", response_ok=True, update_changed_files=False):
+    def actionSiteSign(self, to, privatekey=None, inner_path="content.json", response_ok=True, update_changed_files=False, remove_missing_optional=False):
         self.log.debug("Signing: %s" % inner_path)
         site = self.site
         extend = {}  # Extended info for signing
@@ -320,7 +320,7 @@ class UiWebsocket(object):
         # Reload content.json, ignore errors to make it up-to-date
         site.content_manager.loadContent(inner_path, add_bad_files=False, force=True)
         # Sign using private key sent by user
-        signed = site.content_manager.sign(inner_path, privatekey, extend=extend, update_changed_files=update_changed_files)
+        signed = site.content_manager.sign(inner_path, privatekey, extend=extend, update_changed_files=update_changed_files, remove_missing_optional=remove_missing_optional)
         if not signed:
             self.cmd("notification", ["error", _["Content signing failed"]])
             self.response(to, {"error": "Site sign failed"})
@@ -469,6 +469,13 @@ class UiWebsocket(object):
         ):
             return self.response(to, {"error": "Forbidden, you can only modify your own files"})
 
+        file_info = self.site.content_manager.getFileInfo(inner_path)
+        if file_info.get("optional"):
+            content_json = self.site_storage.loadJson(file_info["content_inner_path"])
+            if inner_path in content_json.get("files_optional", {}):
+                del content_json["files_optional"][inner_path]
+                self.site_storage.writeJson(content_json)
+
         try:
             self.site.storage.delete(inner_path)
         except Exception, err:
diff --git a/src/main.py b/src/main.py
index dbb3c080..5f894271 100644
--- a/src/main.py
+++ b/src/main.py
@@ -188,7 +188,7 @@ class Actions(object):
 
         logging.info("Site created!")
 
-    def siteSign(self, address, privatekey=None, inner_path="content.json", publish=False):
+    def siteSign(self, address, privatekey=None, inner_path="content.json", publish=False, remove_missing_optional=False):
         from Site import Site
         from Site import SiteManager
         SiteManager.site_manager.load()
@@ -208,7 +208,7 @@ class Actions(object):
                 import getpass
                 privatekey = getpass.getpass("Private key (input hidden):")
         diffs = site.content_manager.getDiffs(inner_path)
-        succ = site.content_manager.sign(inner_path=inner_path, privatekey=privatekey, update_changed_files=True)
+        succ = site.content_manager.sign(inner_path=inner_path, privatekey=privatekey, update_changed_files=True, remove_missing_optional=remove_missing_optional)
         if succ and publish:
             self.sitePublish(address, inner_path=inner_path, diffs=diffs)