diff --git a/app/jobs/automation_rules/process_pending_execution_job.rb b/app/jobs/automation_rules/process_pending_execution_job.rb
index d89c6e3ce..4869b25cb 100644
--- a/app/jobs/automation_rules/process_pending_execution_job.rb
+++ b/app/jobs/automation_rules/process_pending_execution_job.rb
@@ -8,8 +8,6 @@ class AutomationRules::ProcessPendingExecutionJob < ApplicationJob
     # Atomic claim: a duplicate enqueue (overlapping sweep or stale reclaim) loses here and returns.
     return unless pending_execution.claim!
 
-    return pending_execution.update!(status: :skipped, skip_reason: 'expired') if expired?(pending_execution)
-
     skip_reason = skip_reason_for(pending_execution)
     return pending_execution.update!(status: :skipped, skip_reason: skip_reason) if skip_reason
 
@@ -21,15 +19,22 @@ class AutomationRules::ProcessPendingExecutionJob < ApplicationJob
 
   private
 
-  def expired?(pending_execution)
-    pending_execution.due_at < AutomationRulePendingExecution::DUE_WINDOW.ago
+  def skip_reason_for(pending_execution)
+    return 'expired' if pending_execution.due_at < AutomationRulePendingExecution::DUE_WINDOW.ago
+
+    structural_skip_reason(pending_execution) || behavioral_skip_reason(pending_execution)
   end
 
-  def skip_reason_for(pending_execution)
+  def structural_skip_reason(pending_execution)
     rule = pending_execution.automation_rule
     return 'rule_inactive' if rule.nil? || !rule.active?
     return 'flag_disabled' unless pending_execution.account.feature_enabled?('delayed_automations')
     return 'conversation_gone' if pending_execution.conversation.nil?
+
+    nil
+  end
+
+  def behavioral_skip_reason(pending_execution)
     return 'episode_moved' unless pending_execution.episode_current?
     return 'conditions_changed' unless conditions_still_match?(pending_execution)