diff --git a/frontend/src/components/Chat/ChatWindow.tsx b/frontend/src/components/Chat/ChatWindow.tsx
index 92249fa02..b4a216c87 100644
--- a/frontend/src/components/Chat/ChatWindow.tsx
+++ b/frontend/src/components/Chat/ChatWindow.tsx
@@ -74,6 +74,10 @@ export default function ChatWindow({
       setIsPanelOpen(true)
     }
   }, [attackResultId, relatedConversationCount])
+  // Set by panel click to bypass the in-flight guard on the next useEffect cycle.
+  // This lets users switch to a sending conversation while still protecting
+  // optimistic messages when handleSend internally updates activeConversationId.
+  const forceLoadRef = useRef(false)
   // Always-current ref of the conversation being viewed so async callbacks can
   // check whether the user navigated away while a request was in-flight.
   const viewedConvRef = useRef(activeConversationId ?? conversationId)
@@ -126,9 +130,12 @@ export default function ChatWindow({
   // Reload messages when activeConversationId changes
   useEffect(() => {
     if (!attackResultId || !activeConversationId) { return }
-    // Skip loading if a send is already in-flight for this conversation —
-    // the send handler will update messages when it completes.
-    if (sendingConvIdsRef.current.has(activeConversationId)) { return }
+    // Allow user-initiated switches (forceLoadRef), but skip re-loading when
+    // handleSend internally updated activeConversationId during an in-flight
+    // send — the optimistic messages are already displayed.
+    const force = forceLoadRef.current
+    forceLoadRef.current = false
+    if (!force && sendingConvIdsRef.current.has(activeConversationId)) { return }
     loadConversation(attackResultId, activeConversationId)
   }, [activeConversationId, attackResultId, loadConversation])
 
@@ -143,6 +150,7 @@ export default function ChatWindow({
   // Handle conversation selection from the panel
   // For a different ID the useEffect handles loading; for same ID force a refresh
   const handlePanelSelectConversation = useCallback((convId: string) => {
+    forceLoadRef.current = true
     onSelectConversation(convId)
     if (convId === activeConversationId && attackResultId) {
       loadConversation(attackResultId, convId)
diff --git a/pyrit/backend/services/attack_service.py b/pyrit/backend/services/attack_service.py
index 5bb4f6bbc..16a8fb704 100644
--- a/pyrit/backend/services/attack_service.py
+++ b/pyrit/backend/services/attack_service.py
@@ -390,6 +390,9 @@ async def get_conversations_async(self, *, attack_result_id: str) -> Optional[At
         for conv_id in active_conv_ids:
             stats = stats_map.get(conv_id)
             created_at = stats.created_at if stats else None
+            # SQLite returns naive datetimes — normalize to UTC (same pattern as _ensure_utc)
+            if created_at is not None and created_at.tzinfo is None:
+                created_at = created_at.replace(tzinfo=timezone.utc)
             conversations.append(
                 ConversationSummary(
                     conversation_id=conv_id,
@@ -399,10 +402,12 @@ async def get_conversations_async(self, *, attack_result_id: str) -> Optional[At
                 )
             )
 
-        # Sort all conversations by created_at (earliest first, None last)
-        conversations.sort(
-            key=lambda c: (c.created_at is None, c.created_at or datetime.min.replace(tzinfo=timezone.utc))
-        )
+        # Sort conversations by created_at (earliest first). In-flight conversations
+        # have no stored messages yet so created_at is None — treat them as the most
+        # recent (they were just created) so they sort after older conversations
+        # instead of jumping to an arbitrary position.
+        now = datetime.now(timezone.utc)
+        conversations.sort(key=lambda c: c.created_at or now)
 
         return AttackConversationsResponse(
             attack_result_id=attack_result_id,