diff --git a/spec/jobs/automation_rules/process_pending_execution_job_spec.rb b/spec/jobs/automation_rules/process_pending_execution_job_spec.rb
index a7c88e9e0..72f755a8a 100644
--- a/spec/jobs/automation_rules/process_pending_execution_job_spec.rb
+++ b/spec/jobs/automation_rules/process_pending_execution_job_spec.rb
@@ -55,15 +55,22 @@ RSpec.describe AutomationRules::ProcessPendingExecutionJob do
     expect(conversation.reload.label_list).to be_empty
   end
 
-  it 'skips with conditions_changed when the re-check no longer matches the edited rule' do
-    pending_execution
-    # Rule edited while pending: the re-check enforces the current conditions (by design).
-    rule.update!(conditions: [{ 'values' => ['open'], 'attribute_key' => 'status', 'query_operator' => nil,
-                                'filter_operator' => 'equal_to' }])
-    job.perform(pending_execution.reload)
+  it 'skips with conditions_changed when the conversation drifts but the episode is intact' do
+    # A message_created (reply-chase) rule whose extra condition is the conversation status.
+    message_rule = create(:automation_rule, account: account, event_name: 'message_created', execution_delay: 60,
+                                            conditions: [{ 'values' => ['pending'], 'attribute_key' => 'status',
+                                                           'query_operator' => nil, 'filter_operator' => 'equal_to' }],
+                                            actions: [{ 'action_name' => 'add_label', 'action_params' => ['stale'] }])
+    agent_reply = create(:message, conversation: conversation, account: account, message_type: :outgoing)
+    AutomationRulePendingExecution.schedule(rule: message_rule, conversation: conversation, message: agent_reply)
+    row = AutomationRulePendingExecution.last
 
-    expect(pending_execution.reload).to be_skipped
-    expect(pending_execution.skip_reason).to eq('conditions_changed')
+    # Status change fails the condition but leaves the reply_chase episode (max incoming id) intact.
+    conversation.update!(status: :open)
+    job.perform(row)
+
+    expect(row.reload).to be_skipped
+    expect(row.skip_reason).to eq('conditions_changed')
   end
 
   it 'skips with expired when the row is past the due window' do
diff --git a/spec/models/automation_rule_pending_execution_spec.rb b/spec/models/automation_rule_pending_execution_spec.rb
index 46b16b3d4..5f9fb153f 100644
--- a/spec/models/automation_rule_pending_execution_spec.rb
+++ b/spec/models/automation_rule_pending_execution_spec.rb
@@ -23,6 +23,18 @@ RSpec.describe AutomationRulePendingExecution do
       expect(described_class.episode_key_for(conversation.reload, message)).to eq("awaiting_agent:#{conversation.waiting_since.to_i}")
     end
 
+    it 'arms an awaiting_agent episode from the message created_at when waiting_since is not yet written' do
+      message = create(:message, conversation: conversation, account: account, message_type: :incoming)
+      # Simulate the race where the listener arms before update_waiting_since commits.
+      conversation.update!(waiting_since: nil)
+      armed_key = described_class.arm_episode_key_for(conversation.reload, message)
+
+      # Once waiting_since settles to the message's created_at, the strict fire-time key matches.
+      conversation.update!(waiting_since: message.created_at)
+      expect(armed_key).to eq("awaiting_agent:#{message.created_at.to_i}")
+      expect(armed_key).to eq(described_class.episode_key_for(conversation.reload, message))
+    end
+
     it 'derives reply_chase episodes from the max incoming message id for outgoing messages' do
       incoming = create(:message, conversation: conversation, account: account, message_type: :incoming)
       outgoing = create(:message, conversation: conversation, account: account, message_type: :outgoing)
diff --git a/spec/models/automation_rule_spec.rb b/spec/models/automation_rule_spec.rb
index 86d611a0f..91bf91df8 100644
--- a/spec/models/automation_rule_spec.rb
+++ b/spec/models/automation_rule_spec.rb
@@ -174,5 +174,60 @@ RSpec.describe AutomationRule do
       expect(rule).not_to be_valid
       expect(rule.errors[:execution_delay]).to include('cannot be used with attribute_changed conditions.')
     end
+
+    it 'rejects a delayed conversation-level rule with a non-status condition' do
+      rule.event_name = 'conversation_updated'
+      rule.execution_delay = 60
+      rule.conditions = [{ 'attribute_key' => 'priority', 'filter_operator' => 'equal_to', 'values' => ['urgent'], 'query_operator' => nil }]
+      expect(rule).not_to be_valid
+      expect(rule.errors[:execution_delay]).to include('only supports status conditions for conversation-level events.')
+    end
+
+    it 'allows a delayed conversation-level rule with only status conditions' do
+      rule.event_name = 'conversation_updated'
+      rule.execution_delay = 60
+      rule.conditions = [{ 'attribute_key' => 'status', 'filter_operator' => 'equal_to', 'values' => ['pending'], 'query_operator' => nil }]
+      expect(rule).to be_valid
+    end
+
+    it 'allows a delayed message_created rule with a non-status condition' do
+      rule.event_name = 'message_created'
+      rule.execution_delay = 60
+      rule.conditions = [{ 'attribute_key' => 'message_type', 'filter_operator' => 'equal_to', 'values' => ['outgoing'], 'query_operator' => nil }]
+      expect(rule).to be_valid
+    end
+  end
+
+  describe 'discarding stale pending executions on edit' do
+    let(:account) { create(:account) }
+    let(:conversation) { create(:conversation, account: account, status: :pending) }
+    let(:status_condition) { { 'attribute_key' => 'status', 'filter_operator' => 'equal_to', 'values' => ['pending'], 'query_operator' => nil } }
+    let(:rule) do
+      create(:automation_rule, account: account, event_name: 'conversation_updated', execution_delay: 60,
+                               conditions: [status_condition], actions: [{ 'action_name' => 'add_label', 'action_params' => ['stale'] }])
+    end
+
+    before { AutomationRulePendingExecution.schedule(rule: rule, conversation: conversation) }
+
+    it 'discards armed rows when the actions change' do
+      rule.update!(actions: [{ 'action_name' => 'add_label', 'action_params' => ['urgent'] }])
+      expect(rule.pending_executions.pending).to be_empty
+    end
+
+    it 'discards armed rows when the delay changes' do
+      rule.update!(execution_delay: 120)
+      expect(rule.pending_executions.pending).to be_empty
+    end
+
+    it 'frees the episode slot so the new definition re-arms for the same episode' do
+      rule.update!(actions: [{ 'action_name' => 'add_label', 'action_params' => ['urgent'] }])
+      AutomationRulePendingExecution.schedule(rule: rule, conversation: conversation)
+      expect(rule.pending_executions.pending.count).to eq(1)
+    end
+
+    it 'leaves armed rows untouched on a name-only edit' do
+      rule.update!(name: 'Renamed rule')
+      expect(rule.pending_executions.pending.count).to eq(1)
+    end
   end
 end