diff --git a/mycroft/skills/__main__.py b/mycroft/skills/__main__.py
index fb6d44605a..51eff48503 100644
--- a/mycroft/skills/__main__.py
+++ b/mycroft/skills/__main__.py
@@ -13,6 +13,7 @@
 # limitations under the License.
 #
 import time
+import datetime as dt
 from threading import Timer
 import mycroft.lock
 from mycroft import dialog
@@ -89,6 +90,14 @@ def _starting_up():
     # Wait until priority skills have been loaded before checking
     # network connection
     skill_manager.load_priority()
+
+    # If device has been offline for more than 2 weeks or
+    # skill state is in a limbo
+    update_limit = dt.datetime.now() - dt.timedelta(days=14)
+    if (not skill_manager.last_download or
+            skill_manager.last_download < update_limit):
+        skill_manager.download_skills(quick=True)
+
     skill_manager.start()
     check_connection()
 
diff --git a/mycroft/skills/skill_manager.py b/mycroft/skills/skill_manager.py
index 1cd758b927..b3854754cd 100644
--- a/mycroft/skills/skill_manager.py
+++ b/mycroft/skills/skill_manager.py
@@ -15,6 +15,7 @@
 import gc
 import sys
 import time
+from datetime import datetime
 from glob import glob
 from itertools import chain
 
@@ -103,9 +104,13 @@ class SkillManager(Thread):
         # Update immediately if the .msm or installed skills file is missing
         # otherwise according to timestamp on .msm
         if exists(self.dot_msm) and exists(self.installed_skills_file):
-            self.next_download = os.path.getmtime(self.dot_msm) + \
-                                 self.update_interval
+            mtime = os.path.getmtime(self.dot_msm)
+            self.next_download = mtime + self.update_interval
+            self.last_download = datetime.fromtimestamp(mtime)
         else:
+            # Last update can't be found or the requirements don't seem to be
+            # installed trigger update before skill loading
+            self.last_download = None
             self.next_download = time.time() - 1
 
         # Conversation management
@@ -380,10 +385,6 @@ class SkillManager(Thread):
         # Scan the file folder that contains Skills.  If a Skill is updated,
         # unload the existing version from memory and reload from the disk.
         while not self._stop_event.is_set():
-            # Update skills once an hour if update is enabled
-            if time.time() >= self.next_download and update:
-                self.download_skills()
-
             # Look for recently changed skill(s) needing a reload
             # checking skills dir and getting all skills there
             skill_paths = glob(join(self.msm.skills_dir, '*/'))
@@ -406,6 +407,10 @@ class SkillManager(Thread):
             # Pause briefly before beginning next scan
             time.sleep(2)
 
+            # Update skills once an hour if update is enabled
+            if time.time() >= self.next_download and update:
+                self.download_skills()
+
     def send_skill_list(self, message=None):
         """
             Send list of loaded skills.