diff --git a/apps/web/src/hooks/useChat.ts b/apps/web/src/hooks/useChat.ts
index 881e9a4..c9fe796 100644
--- a/apps/web/src/hooks/useChat.ts
+++ b/apps/web/src/hooks/useChat.ts
@@ -343,63 +343,64 @@ export function useChat(options: UseChatOptions = {}): UseChatReturn {
             error: err instanceof Error ? err : new Error(String(err)),
           });
 
-        setMessages((prev) => {
-          const withoutPlaceholder = prev.filter((m) => m.id !== assistantMessageId);
-          messagesRef.current = withoutPlaceholder;
-          return withoutPlaceholder;
-        });
-        setIsStreaming(false);
-
-        try {
-          const response = await sendChatMessage(request);
-
-          const assistantMessage: Message = {
-            id: `assistant-${Date.now().toString()}`,
-            role: "assistant",
-            content: response.message.content,
-            createdAt: new Date().toISOString(),
-            model: response.model,
-            promptTokens: response.promptEvalCount ?? 0,
-            completionTokens: response.evalCount ?? 0,
-            totalTokens: (response.promptEvalCount ?? 0) + (response.evalCount ?? 0),
-          };
-
           setMessages((prev) => {
-            const updated = [...prev, assistantMessage];
-            messagesRef.current = updated;
-            return updated;
+            const withoutPlaceholder = prev.filter((m) => m.id !== assistantMessageId);
+            messagesRef.current = withoutPlaceholder;
+            return withoutPlaceholder;
           });
+          setIsStreaming(false);
 
-          streamingSucceeded = true;
-        } catch (fallbackErr: unknown) {
-          const errorMsg =
-            fallbackErr instanceof Error ? fallbackErr.message : "Failed to send message";
-          setError("Unable to send message. Please try again.");
-          onError?.(fallbackErr instanceof Error ? fallbackErr : new Error(errorMsg));
-          console.error("Failed to send chat message", {
-            error: fallbackErr,
-            errorType: "LLM_ERROR",
-            conversationId: conversationIdRef.current,
-            messageLength: content.length,
-            messagePreview: content.substring(0, 50),
-            model,
-            messageCount: messagesRef.current.length,
-            timestamp: new Date().toISOString(),
-          });
+          try {
+            const response = await sendChatMessage(request);
 
-          const errorMessage: Message = {
-            id: `error-${String(Date.now())}`,
-            role: "assistant",
-            content: "Something went wrong. Please try again.",
-            createdAt: new Date().toISOString(),
-          };
-          setMessages((prev) => {
-            const updated = [...prev, errorMessage];
-            messagesRef.current = updated;
-            return updated;
-          });
-          setIsLoading(false);
-          return;
+            const assistantMessage: Message = {
+              id: `assistant-${Date.now().toString()}`,
+              role: "assistant",
+              content: response.message.content,
+              createdAt: new Date().toISOString(),
+              model: response.model,
+              promptTokens: response.promptEvalCount ?? 0,
+              completionTokens: response.evalCount ?? 0,
+              totalTokens: (response.promptEvalCount ?? 0) + (response.evalCount ?? 0),
+            };
+
+            setMessages((prev) => {
+              const updated = [...prev, assistantMessage];
+              messagesRef.current = updated;
+              return updated;
+            });
+
+            streamingSucceeded = true;
+          } catch (fallbackErr: unknown) {
+            const errorMsg =
+              fallbackErr instanceof Error ? fallbackErr.message : "Failed to send message";
+            setError("Unable to send message. Please try again.");
+            onError?.(fallbackErr instanceof Error ? fallbackErr : new Error(errorMsg));
+            console.error("Failed to send chat message", {
+              error: fallbackErr,
+              errorType: "LLM_ERROR",
+              conversationId: conversationIdRef.current,
+              messageLength: content.length,
+              messagePreview: content.substring(0, 50),
+              model,
+              messageCount: messagesRef.current.length,
+              timestamp: new Date().toISOString(),
+            });
+
+            const errorMessage: Message = {
+              id: `error-${String(Date.now())}`,
+              role: "assistant",
+              content: "Something went wrong. Please try again.",
+              createdAt: new Date().toISOString(),
+            };
+            setMessages((prev) => {
+              const updated = [...prev, errorMessage];
+              messagesRef.current = updated;
+              return updated;
+            });
+            setIsLoading(false);
+            return;
+          }
         }
       }