diff --git a/app/reddit/tasks.py b/app/reddit/tasks.py
index b089df4..7910ea5 100644
--- a/app/reddit/tasks.py
+++ b/app/reddit/tasks.py
@@ -83,11 +83,22 @@ def queue_account_updates(update_delay=604800, batch_size=50):
         update_account.delay(username=acc.pk)
 
 
-@task(ignore_result=True)
-def update_user_flair(username, character_name):
-    try:
-        ib = Flair(username=settings.REDDIT_USER, password=settings.REDDIT_PASSWORD)
-        ib.set_flair(settings.REDDIT_SUBREDDIT, username, character_name, '')
-    except LoginError, exc:
-        logger.error("Error logging into Reddit")
+class update_user_flair(Task):
+    """
+    Updates a user's flair on Reddit
+    """
+
+    default_retry_delay = 5 * 60 # retry in 5 minutes
+    ignore_result = True
+
+    def run(self, username, character_name, **kwargs):
+        try:
+            ib = Flair(username=settings.REDDIT_USER, password=settings.REDDIT_PASSWORD)
+            ib.set_flair(settings.REDDIT_SUBREDDIT, username, character_name, '')
+        except (HTTPError, URLError), exc:
+            logger.error("Error updating flair, queueing for retry")
+            update_user_flair.retry(args=[username, character_name], kwargs=kwargs, exc=exc)
+            pass
+        except LoginError, exc:
+            logger.error("Error logging into Reddit")
 
diff --git a/app/sso/views.py b/app/sso/views.py
index a64fdd7..286385b 100644
--- a/app/sso/views.py
+++ b/app/sso/views.py
@@ -293,18 +293,22 @@ def primarychar_change(request):
 @login_required
 def toggle_reddit_tagging(request):
     profile = request.user.get_profile()
-    profile.tag_reddit_accounts = not profile.tag_reddit_accounts
-    profile.save()
-    if profile.tag_reddit_accounts:
-        tag = 'Enabled'
-    else:
-        tag = 'Disabled'
-    messages.add_message(request, messages.INFO, "Reddit account tagging is now %s" % tag)
+    if profile.primary_character:
+        profile.tag_reddit_accounts = not profile.tag_reddit_accounts
+        profile.save()
+        if profile.tag_reddit_accounts:
+            tag = 'Enabled'
+        else:
+            tag = 'Disabled'
+        messages.add_message(request, messages.INFO, "Reddit account tagging is now %s" % tag)
 
-    if profile.tag_reddit_accounts:
-        name = profile.primary_character.name
+        if profile.tag_reddit_accounts:
+            name = profile.primary_character.name
+        else:
+            name = ''
+        for acc in request.user.redditaccount_set.all():
+            update_user_flair.delay(acc.username, name)
     else:
-        name = ''
-    for acc in request.user.redditaccount_set.all():
-        update_user_flair.delay(acc.username, name)
+        messages.add_message(request, messages.ERROR, "You need to set a primary character before using this feature!")
+
     return redirect('sso.views.profile')