diff --git a/app/javascript/dashboard/routes/dashboard/settings/automation/AutomationRuleForm.vue b/app/javascript/dashboard/routes/dashboard/settings/automation/AutomationRuleForm.vue
index 7f405f4d6..10fe92b9d 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/automation/AutomationRuleForm.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/automation/AutomationRuleForm.vue
@@ -311,10 +311,12 @@ const resetToSupportedCondition = () => {
   ];
 };
 
-// Turning on a delay narrows the condition options; reset only the conditions a delayed rule
-// can't use (e.g. a mutable attribute) to a supported default. Actions are kept.
-watch(isDelayed, delayed => {
-  if (!delayed || !automation.value) return;
+// A delay narrows the condition options, so whenever the rule becomes unsupported while the
+// wait is on — toggling it on, or switching to an event whose default condition isn't allowed
+// (e.g. conversation_opened defaults to browser_language) — reset to a supported default.
+// Actions are kept. Resetting makes the rule supported again, so this can't loop.
+watch([isDelayed, isDelaySupported], () => {
+  if (!isDelayed.value || !automation.value) return;
   if (!isDelaySupported.value) resetToSupportedCondition();
 });
 
diff --git a/app/models/automation_rule_pending_execution.rb b/app/models/automation_rule_pending_execution.rb
index c0e2b5bd6..455312f64 100644
--- a/app/models/automation_rule_pending_execution.rb
+++ b/app/models/automation_rule_pending_execution.rb
@@ -62,7 +62,11 @@ class AutomationRulePendingExecution < ApplicationRecord
     return unless message && !message.incoming?
 
     row = find_by!(automation_rule_id: rule.id, conversation_id: conversation.id, episode_key: key)
-    row.update!(due_at: rule.execution_delay.minutes.since(anchor), message_id: message.id) if row.pending?
+    # Jobs can arrive out of order; only a newer reply moves the clock, so a late older reply
+    # can't pull due_at backwards and fire before the delay elapses since the latest reply.
+    return unless row.pending? && message.id > row.message_id
+
+    row.update!(due_at: rule.execution_delay.minutes.since(anchor), message_id: message.id)
   end
 
   # The wait is measured from when the qualifying event happened, not when this (possibly