diff --git a/backend/app/services/assistant_chat_service.py b/backend/app/services/assistant_chat_service.py
index 6e17b8e3..184fd744 100644
--- a/backend/app/services/assistant_chat_service.py
+++ b/backend/app/services/assistant_chat_service.py
@@ -303,6 +303,8 @@ async def _call_anthropic_cached(
             }
         ]
 
+    _mcp_active = mcp_servers is not anthropic.NOT_GIVEN
+
     try:
         response = await client.beta.messages.create(
             model=settings.AI_MODEL_ANTHROPIC,
@@ -313,12 +315,22 @@ async def _call_anthropic_cached(
             tools=tools,
             betas=["mcp-client-2025-11-20"],
         )
-    except anthropic.BadRequestError as e:
-        # MCP server failures (rate limits, connection errors) should not
-        # block the assistant entirely — retry without MCP tools.
-        if "MCP server" in str(e) and mcp_servers is not anthropic.NOT_GIVEN:
-            logger.warning("MCP server error, retrying without MCP: %s", e)
-            response = await client.beta.messages.create(
+    except Exception as e:
+        # MCP server failures surface as many error types — BadRequestError,
+        # APIStatusError, APIConnectionError, APITimeoutError.  Always retry
+        # without MCP when MCP was active, so a flaky external server never
+        # blocks the assistant entirely.
+        _is_mcp_error = _mcp_active and (
+            "MCP server" in str(e)
+            or "mcp" in type(e).__name__.lower()
+            or isinstance(e, (anthropic.BadRequestError, anthropic.APIStatusError))
+        )
+        if _is_mcp_error:
+            logger.warning(
+                "MCP server error (%s), retrying without MCP: %s",
+                type(e).__name__, e,
+            )
+            response = await client.messages.create(
                 model=settings.AI_MODEL_ANTHROPIC,
                 max_tokens=max_tokens,
                 system=system_blocks,
diff --git a/frontend/src/components/assistant/ChatMessage.tsx b/frontend/src/components/assistant/ChatMessage.tsx
index d905aada..c9a214d2 100644
--- a/frontend/src/components/assistant/ChatMessage.tsx
+++ b/frontend/src/components/assistant/ChatMessage.tsx
@@ -7,9 +7,10 @@ interface ChatMessageProps {
   role: 'user' | 'assistant'
   content: string
   suggestedFlows?: SuggestedFlow[]
+  imageUrls?: string[]
 }
 
-export function ChatMessage({ role, content, suggestedFlows }: ChatMessageProps) {
+export function ChatMessage({ role, content, suggestedFlows, imageUrls }: ChatMessageProps) {
   return (
     <div className={`flex gap-3 ${role === 'user' ? 'flex-row-reverse' : ''}`}>
       {/* Avatar */}
@@ -25,6 +26,21 @@ export function ChatMessage({ role, content, suggestedFlows }: ChatMessageProps)
 
       {/* Content */}
       <div className={`max-w-[80%] space-y-2 ${role === 'user' ? 'text-right' : ''}`}>
+        {/* Image attachments (user messages only) */}
+        {role === 'user' && imageUrls && imageUrls.length > 0 && (
+          <div className={`flex flex-wrap gap-2 ${role === 'user' ? 'justify-end' : ''}`}>
+            {imageUrls.map((url, i) => (
+              <a key={i} href={url} target="_blank" rel="noopener noreferrer">
+                <img
+                  src={url}
+                  alt={`Attachment ${i + 1}`}
+                  className="h-24 w-auto max-w-[200px] rounded-xl object-cover border border-border cursor-pointer hover:opacity-90 transition-opacity"
+                />
+              </a>
+            ))}
+          </div>
+        )}
+
         <div
           className={`rounded-2xl px-4 py-3 text-[0.875rem] leading-relaxed ${
             role === 'user'
diff --git a/frontend/src/pages/AssistantChatPage.tsx b/frontend/src/pages/AssistantChatPage.tsx
index ab500fec..e7381287 100644
--- a/frontend/src/pages/AssistantChatPage.tsx
+++ b/frontend/src/pages/AssistantChatPage.tsx
@@ -25,6 +25,7 @@ interface MessageWithMeta {
   fork?: ForkMetadata | null
   actions?: ActionItem[] | null
   questions?: QuestionItem[] | null
+  imageUrls?: string[]
 }
 
 export default function AssistantChatPage() {
@@ -322,12 +323,14 @@ export default function AssistantChatPage() {
     if (!input.trim() || !activeChatId || loading) return
 
     const userMessage = input.trim()
-    const completedUploadIds = pendingUploads
-      .filter((u) => u.status === 'done' && u.result?.id)
-      .map((u) => u.result!.id)
+    const completedUploads = pendingUploads.filter((u) => u.status === 'done' && u.result?.id)
+    const completedUploadIds = completedUploads.map((u) => u.result!.id)
+    const imageUrls = completedUploads
+      .filter((u) => u.preview)
+      .map((u) => u.preview)
     setInput('')
     setPendingUploads([])
-    setMessages(prev => [...prev, { role: 'user', content: userMessage }])
+    setMessages(prev => [...prev, { role: 'user', content: userMessage, imageUrls: imageUrls.length > 0 ? imageUrls : undefined }])
     setLoading(true)
 
     const sentForChatId = activeChatId
@@ -363,11 +366,21 @@ export default function AssistantChatPage() {
         setActiveActions(response.actions || [])
         setShowTaskLane(true)
       }
-    } catch {
-      setMessages(prev => [
-        ...prev,
-        { role: 'assistant', content: 'Sorry, something went wrong. Please try again.' },
-      ])
+    } catch (err: unknown) {
+      console.error('[AssistantChat] sendChatMessage failed:', err)
+      const status = (err as { response?: { status?: number } })?.response?.status
+      let errorMsg: string
+      if (status === 429) {
+        errorMsg = "You're sending messages too quickly. Wait a moment and try again."
+      } else if (status === 502 || status === 503) {
+        errorMsg = "The AI is temporarily unavailable. Please try again in a few seconds."
+      } else {
+        errorMsg = "Something went wrong sending your message. Please try again."
+      }
+      // Remove the optimistic user message and restore it to the input so they can retry
+      setMessages(prev => prev.slice(0, -1))
+      setInput(userMessage)
+      toast.error(errorMsg)
     } finally {
       setLoading(false)
       requestAnimationFrame(() => inputRef.current?.focus())
@@ -421,11 +434,14 @@ export default function AssistantChatPage() {
         setActiveQuestions([])
         setActiveActions([])
       }
-    } catch {
-      setMessages(prev => [
-        ...prev,
-        { role: 'assistant', content: 'Sorry, something went wrong processing your responses. Please try again.' },
-      ])
+    } catch (err: unknown) {
+      console.error('[AssistantChat] handleTaskSubmit failed:', err)
+      const status = (err as { response?: { status?: number } })?.response?.status
+      const errorMsg = status === 429
+        ? "You're sending messages too quickly. Wait a moment and try again."
+        : "Something went wrong submitting your responses. Please try again."
+      setMessages(prev => prev.slice(0, -1))
+      toast.error(errorMsg)
     } finally {
       setLoading(false)
     }
@@ -832,6 +848,7 @@ export default function AssistantChatPage() {
                   role={msg.role}
                   content={msg.content}
                   suggestedFlows={msg.suggestedFlows}
+                  imageUrls={msg.imageUrls}
                 />
               ))}
               {loading && (