diff --git a/hld/session/manager.go b/hld/session/manager.go
index 2c43c1c5..39626adf 100644
--- a/hld/session/manager.go
+++ b/hld/session/manager.go
@@ -1028,6 +1028,7 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 				EventType:       store.EventTypeSystem,
 				Role:            "system",
 				Content:         fmt.Sprintf("Session created with ID: %s", event.SessionID),
+				ParentToolUseID: event.ParentToolUseID,
 			}
 			if err := m.store.AddConversationEvent(ctx, convEvent); err != nil {
 				return err
@@ -1038,12 +1039,13 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 				m.eventBus.Publish(bus.Event{
 					Type: bus.EventConversationUpdated,
 					Data: map[string]interface{}{
-						"session_id":        sessionID,
-						"claude_session_id": claudeSessionID,
-						"event_type":        "system",
-						"subtype":           event.Subtype,
-						"content":           fmt.Sprintf("Session created with ID: %s", event.SessionID),
-						"content_type":      "system",
+						"session_id":         sessionID,
+						"claude_session_id":  claudeSessionID,
+						"event_type":         "system",
+						"subtype":            event.Subtype,
+						"content":            fmt.Sprintf("Session created with ID: %s", event.SessionID),
+						"content_type":       "system",
+						"parent_tool_use_id": event.ParentToolUseID,
 					},
 				})
 			}
@@ -1125,6 +1127,7 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 						EventType:       store.EventTypeMessage,
 						Role:            event.Message.Role,
 						Content:         content.Text,
+						ParentToolUseID: event.ParentToolUseID,
 					}
 					if err := m.store.AddConversationEvent(ctx, convEvent); err != nil {
 						return err
@@ -1138,12 +1141,13 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 						m.eventBus.Publish(bus.Event{
 							Type: bus.EventConversationUpdated,
 							Data: map[string]interface{}{
-								"session_id":        sessionID,
-								"claude_session_id": claudeSessionID,
-								"event_type":        "message",
-								"role":              event.Message.Role,
-								"content":           content.Text,
-								"content_type":      "text",
+								"session_id":         sessionID,
+								"claude_session_id":  claudeSessionID,
+								"event_type":         "message",
+								"role":               event.Message.Role,
+								"content":            content.Text,
+								"content_type":       "text",
+								"parent_tool_use_id": event.ParentToolUseID,
 							},
 						})
 					}
@@ -1204,6 +1208,7 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 						Role:              "user",
 						ToolResultForID:   content.ToolUseID,
 						ToolResultContent: content.Content.Value,
+						ParentToolUseID:   event.ParentToolUseID,
 					}
 					if err := m.store.AddConversationEvent(ctx, convEvent); err != nil {
 						return err
@@ -1228,6 +1233,7 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 								"tool_result_for_id":  content.ToolUseID,
 								"tool_result_content": content.Content.Value,
 								"content_type":        "tool_result",
+								"parent_tool_use_id":  event.ParentToolUseID,
 							},
 						})
 					}
@@ -1249,6 +1255,7 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 						EventType:       store.EventTypeThinking,
 						Role:            event.Message.Role,
 						Content:         content.Thinking,
+						ParentToolUseID: event.ParentToolUseID,
 					}
 					if err := m.store.AddConversationEvent(ctx, convEvent); err != nil {
 						return err
@@ -1262,12 +1269,13 @@ func (m *Manager) processStreamEvent(ctx context.Context, sessionID string, clau
 						m.eventBus.Publish(bus.Event{
 							Type: bus.EventConversationUpdated,
 							Data: map[string]interface{}{
-								"session_id":        sessionID,
-								"claude_session_id": claudeSessionID,
-								"event_type":        "thinking",
-								"role":              event.Message.Role,
-								"content":           content.Thinking,
-								"content_type":      "thinking",
+								"session_id":         sessionID,
+								"claude_session_id":  claudeSessionID,
+								"event_type":         "thinking",
+								"role":               event.Message.Role,
+								"content":            content.Thinking,
+								"content_type":       "thinking",
+								"parent_tool_use_id": event.ParentToolUseID,
 							},
 						})
 					}
diff --git a/humanlayer-wui/src/components/internal/SessionDetail/components/ActiveSession.tsx b/humanlayer-wui/src/components/internal/SessionDetail/components/ActiveSession.tsx
index aa42a178..d5322ea2 100644
--- a/humanlayer-wui/src/components/internal/SessionDetail/components/ActiveSession.tsx
+++ b/humanlayer-wui/src/components/internal/SessionDetail/components/ActiveSession.tsx
@@ -306,6 +306,7 @@ export function ActiveSession({ session, onClose }: ActiveSessionProps) {
 
   // Check if there are pending approvals out of view
   const [hasPendingApprovalsOutOfView, setHasPendingApprovalsOutOfView] = useState(false)
+  const [pendingApprovalsCount, setPendingApprovalsCount] = useState(0)
 
   const lastTodo = events
     ?.toReversed()
@@ -770,8 +771,12 @@ export function ActiveSession({ session, onClose }: ActiveSessionProps) {
   useEffect(() => {
     const checkPendingApprovalVisibility = () => {
       if (session.status === SessionStatus.WaitingInput) {
-        const pendingEvent = events.find(e => e.approvalStatus === ApprovalStatus.Pending)
-        if (pendingEvent) {
+        const pendingEvents = events.filter(e => e.approvalStatus === ApprovalStatus.Pending)
+        setPendingApprovalsCount(pendingEvents.length)
+
+        if (pendingEvents.length > 0) {
+          // Check visibility of the first pending approval
+          const pendingEvent = pendingEvents[0]
           const container = document.querySelector('[data-conversation-container]')
           const element = container?.querySelector(`[data-event-id="${pendingEvent.id}"]`)
           if (container && element) {
@@ -796,6 +801,7 @@ export function ActiveSession({ session, onClose }: ActiveSessionProps) {
           setHasPendingApprovalsOutOfView(false)
         }
       } else {
+        setPendingApprovalsCount(0)
         setHasPendingApprovalsOutOfView(false)
       }
     }
@@ -918,7 +924,11 @@ export function ActiveSession({ session, onClose }: ActiveSessionProps) {
               }}
             >
               <div className="flex items-center justify-center gap-1 font-mono text-xs uppercase tracking-wider text-muted-foreground bg-background/60 backdrop-blur-sm border-t border-border/50 py-1 shadow-sm hover:bg-background/80 transition-colors">
-                <span>Pending Approval</span>
+                <span>
+                  {pendingApprovalsCount === 1
+                    ? 'Pending Approval'
+                    : `${pendingApprovalsCount} Pending Approvals`}
+                </span>
                 <ChevronDown className="w-3 h-3 animate-bounce" />
               </div>
             </div>