diff --git a/CTFd/__init__.py b/CTFd/__init__.py
index 5b48e867..36f48609 100644
--- a/CTFd/__init__.py
+++ b/CTFd/__init__.py
@@ -43,6 +43,22 @@ class ThemeLoader(FileSystemLoader):
         return super(ThemeLoader, self).get_source(environment, template)
 
 
+def confirm_upgrade():
+    print("/*\\ CTFd has updated and must update the database! /*\\")
+    print("/*\\ Please backup your database before proceeding! /*\\")
+    print("/*\\ CTFd maintainers are not responsible for any data loss! /*\\")
+    if input('Run database migrations (Y/N)').lower().strip() == 'y':
+        return True
+    else:
+        print('/*\\ Ignored database migrations... /*\\')
+        return False
+
+
+def run_upgrade():
+    migrate_upgrade()
+    utils.set_config('ctf_version', __version__)
+
+
 def create_app(config='CTFd.config.Config'):
     app = Flask(__name__)
     with app.app_context():
@@ -79,10 +95,18 @@ def create_app(config='CTFd.config.Config'):
         if url.drivername.startswith('sqlite'):
             db.create_all()
         else:
-            if 'alembic_version' not in db.engine.table_names():
+            if len(db.engine.table_names()) == 0:
                 # This creates tables instead of db.create_all()
                 # Allows migrations to happen properly
                 migrate_upgrade()
+            elif 'alembic_version' not in db.engine.table_names():
+                # There is no alembic_version because CTFd is from before it had migrations
+                # Stamp it to the base migration
+                if confirm_upgrade():
+                    migrate_stamp(revision='cb3cfcc47e2f')
+                    run_upgrade()
+                else:
+                    exit()
 
         app.db = db
 
@@ -91,19 +115,11 @@ def create_app(config='CTFd.config.Config'):
 
         version = utils.get_config('ctf_version')
 
-        if not version:  # Upgrading from an unversioned CTFd
-            utils.set_config('ctf_version', __version__)
-
-        if version and (StrictVersion(version) < StrictVersion(__version__)):  # Upgrading from an older version of CTFd
-            print("/*\\ CTFd has updated and must update the database! /*\\")
-            print("/*\\ Please backup your database before proceeding! /*\\")
-            print("/*\\ CTFd maintainers are not responsible for any data loss! /*\\")
-            if input('Run database migrations (Y/N)').lower().strip() == 'y':
-                migrate_stamp()
-                migrate_upgrade()
-                utils.set_config('ctf_version', __version__)
+        # Upgrading from an older version of CTFd
+        if version and (StrictVersion(version) < StrictVersion(__version__)):
+            if confirm_upgrade():
+                run_upgrade()
             else:
-                print('/*\\ Ignored database migrations... /*\\')
                 exit()
 
         if not utils.get_config('ctf_theme'):