diff --git a/ruby/lib/jam_ruby/models/user.rb b/ruby/lib/jam_ruby/models/user.rb
index 4b6aa8752..d6324131c 100644
--- a/ruby/lib/jam_ruby/models/user.rb
+++ b/ruby/lib/jam_ruby/models/user.rb
@@ -398,7 +398,7 @@ module JamRuby
         any = false
         User
             .where('subscription_last_checked_at is NULL OR users.subscription_last_checked_at < ?', 1.days.ago)
-            .where("recurly_subscription_id IS NOT NULL OR subscription_sync_code  IS NULL or subscription_sync_code not in (subscription_sync_code not in ('trial_ended', 'no_recurly_account', 'admin_control', 'school_license', 'no_subscription_or_expired'))")
+            .where("recurly_subscription_id IS NOT NULL OR subscription_sync_code  IS NULL or (subscription_sync_code not in ('trial_ended', 'no_recurly_account', 'admin_control', 'school_license', 'no_subscription_or_expired'))")
             .order('subscription_last_checked_at ASC NULLS FIRST, recurly_code ASC NULLS LAST')
             .limit(1000)
             .each do |user|