diff --git a/frontend/src/components/DashboardChatInput.vue b/frontend/src/components/DashboardChatInput.vue
index cf5fea9..a761a74 100644
--- a/frontend/src/components/DashboardChatInput.vue
+++ b/frontend/src/components/DashboardChatInput.vue
@@ -126,7 +126,7 @@ defineExpose({ focus });
         <button
           class="btn-attach"
           @click="toggleNotePicker"
-          :disabled="!store.chatReady || store.streaming"
+          :disabled="!store.chatReady"
           title="Attach a note"
         >
           <svg
@@ -181,17 +181,17 @@ defineExpose({ focus });
         @input="autoResize"
         :placeholder="
           !store.chatReady ? 'Chat unavailable'
-          : store.streaming ? 'Generating response…'
+          : store.streaming ? 'Type to queue… (Enter to queue)'
           : 'Start a new chat… (Enter to send)'
         "
-        :disabled="!store.chatReady || store.streaming"
+        :disabled="!store.chatReady"
         rows="1"
       ></textarea>
 
       <button
         class="btn-send"
         @click="onSubmit"
-        :disabled="!messageInput.trim() || !store.chatReady || store.streaming"
+        :disabled="!messageInput.trim() || !store.chatReady"
       >
         &uarr;
       </button>
diff --git a/frontend/src/components/ToolCallCard.vue b/frontend/src/components/ToolCallCard.vue
index c4230f8..067b51c 100644
--- a/frontend/src/components/ToolCallCard.vue
+++ b/frontend/src/components/ToolCallCard.vue
@@ -1,17 +1,20 @@
 <script setup lang="ts">
 import { computed, ref, watch } from "vue";
 import { apiPost } from "@/api/client";
+import { useChatStore } from "@/stores/chat";
 import type { ToolCallRecord } from "@/types/chat";
 
 const props = defineProps<{
   toolCall: ToolCallRecord;
 }>();
 
+const chatStore = useChatStore();
 const appliedTags = ref<Set<string>>(new Set());
 const applyingTag = ref<string | null>(null);
 
 const label = computed(() => {
   if (props.toolCall.status === "declined") return "Declined";
+  if (props.toolCall.result.requires_confirmation) return "Similar content found";
   if (!props.toolCall.result.success) return "Error";
   switch (props.toolCall.result.type) {
     case "task":        return "Created task";
@@ -210,6 +213,14 @@ function toggle() {
   if (hasDetail.value) collapsed.value = !collapsed.value;
 }
 
+function confirmDuplicate() {
+  chatStore.sendMessage("Yes, please create it.", null, undefined, true);
+}
+
+function denyDuplicate() {
+  chatStore.sendMessage("No, skip that creation.", null, undefined, true);
+}
+
 async function applyTag(tag: string) {
   if (!noteId.value || appliedTags.value.has(tag) || applyingTag.value) return;
   applyingTag.value = tag;
@@ -228,7 +239,8 @@ async function applyTag(tag: string) {
   <div
     class="tool-call-card"
     :class="{
-      error: toolCall.status === 'error',
+      error: toolCall.status === 'error' && !toolCall.result.requires_confirmation,
+      'requires-confirm': toolCall.result.requires_confirmation,
       declined: toolCall.status === 'declined',
       running: toolCall.status === 'running',
       collapsible: hasDetail,
@@ -244,6 +256,15 @@ async function applyTag(tag: string) {
           {{ toolCall.arguments.title ?? toolCall.arguments.summary ?? toolCall.arguments.query ?? toolCall.function }}
         </span>
       </template>
+      <template v-else-if="toolCall.result.requires_confirmation">
+        <router-link
+          v-if="toolCall.result.similar_note"
+          :to="`/notes/${toolCall.result.similar_note.id}`"
+          class="tool-link"
+          @click.stop
+        >{{ toolCall.result.similar_note.title }}</router-link>
+        <span v-else class="tool-error">{{ toolCall.result.error }}</span>
+      </template>
       <template v-else-if="toolCall.status === 'error'">
         <span class="tool-error">{{ toolCall.result.error }}</span>
       </template>
@@ -305,6 +326,12 @@ async function applyTag(tag: string) {
       <span v-if="hasDetail" class="tool-chevron" :class="{ open: !collapsed }">▶</span>
     </div>
 
+    <!-- Duplicate confirmation actions -->
+    <div v-if="toolCall.result.requires_confirmation" class="duplicate-confirm-actions">
+      <button class="btn-confirm-duplicate" @click="confirmDuplicate">Create Anyway</button>
+      <button class="btn-deny-duplicate" @click="denyDuplicate">Don't Create</button>
+    </div>
+
     <!-- ── Detail section (expandable) ─────────────────────────── -->
     <div v-if="hasDetail" v-show="!collapsed" class="tool-card-detail">
       <template v-if="noteContent && noteContent.tags.length">
@@ -577,4 +604,40 @@ async function applyTag(tag: string) {
 }
 .tag-pill:disabled:not(.applied) { opacity: 0.6; cursor: wait; }
 .tag-check { font-size: 0.65rem; }
+
+/* Duplicate confirmation */
+.tool-call-card.requires-confirm {
+  border-color: color-mix(in srgb, var(--color-warning, #f59e0b) 60%, transparent);
+}
+.duplicate-confirm-actions {
+  display: flex;
+  gap: 0.4rem;
+  padding: 0.4rem 0.6rem;
+  border-top: 1px solid var(--color-border);
+}
+.btn-confirm-duplicate {
+  padding: 0.25rem 0.7rem;
+  background: var(--color-primary);
+  color: #fff;
+  border: none;
+  border-radius: var(--radius-sm, 6px);
+  cursor: pointer;
+  font-size: 0.78rem;
+  font-family: inherit;
+}
+.btn-confirm-duplicate:hover { opacity: 0.9; }
+.btn-deny-duplicate {
+  padding: 0.25rem 0.7rem;
+  background: none;
+  color: var(--color-text-muted);
+  border: 1px solid var(--color-border);
+  border-radius: var(--radius-sm, 6px);
+  cursor: pointer;
+  font-size: 0.78rem;
+  font-family: inherit;
+}
+.btn-deny-duplicate:hover {
+  color: var(--color-danger, #e74c3c);
+  border-color: var(--color-danger, #e74c3c);
+}
 </style>
diff --git a/frontend/src/stores/chat.ts b/frontend/src/stores/chat.ts
index 7a84661..40a4942 100644
--- a/frontend/src/stores/chat.ts
+++ b/frontend/src/stores/chat.ts
@@ -84,6 +84,11 @@ export const useChatStore = defineStore("chat", () => {
     return id ? (convQueues.value[id]?.length ?? 0) : 0;
   });
 
+  const queuedMessages = computed(() => {
+    const id = currentConversation.value?.id;
+    return id ? (convQueues.value[id] ?? []) : [];
+  });
+
   function clearQueue() {
     const id = currentConversation.value?.id;
     if (id) convQueues.value[id] = [];
@@ -556,6 +561,7 @@ export const useChatStore = defineStore("chat", () => {
     chatReady,
     isStreamingConv,
     queuedCount,
+    queuedMessages,
     clearQueue,
     fetchConversations,
     createConversation,
diff --git a/frontend/src/types/chat.ts b/frontend/src/types/chat.ts
index be65bdb..ad430ea 100644
--- a/frontend/src/types/chat.ts
+++ b/frontend/src/types/chat.ts
@@ -9,7 +9,7 @@ export interface GenerationTiming {
 export interface ToolCallRecord {
   function: string;
   arguments: Record<string, unknown>;
-  result: { success: boolean; type?: string; data?: Record<string, unknown>; error?: string; suggested_tags?: string[] };
+  result: { success: boolean; type?: string; data?: Record<string, unknown>; error?: string; suggested_tags?: string[]; requires_confirmation?: boolean; similar_note?: { id: number; title: string } };
   status: "running" | "success" | "error" | "declined";
 }
 
diff --git a/frontend/src/views/ChatView.vue b/frontend/src/views/ChatView.vue
index 374a504..1439058 100644
--- a/frontend/src/views/ChatView.vue
+++ b/frontend/src/views/ChatView.vue
@@ -632,12 +632,24 @@ onUnmounted(() => {
                 </div>
               </div>
 
-              <!-- Queued message indicator -->
-              <div v-if="store.queuedCount" class="queued-indicator">
-                <span class="queued-icon">⏳</span>
-                {{ store.queuedCount }} message{{ store.queuedCount > 1 ? 's' : '' }} queued
-                <button class="queued-cancel" @click="store.clearQueue()" aria-label="Cancel queued messages">×</button>
-              </div>
+              <!-- Queued messages — shown as pending bubbles -->
+              <template v-if="store.queuedMessages.length">
+                <div
+                  v-for="(q, i) in store.queuedMessages"
+                  :key="`queued-${i}`"
+                  class="chat-message role-user queued-message"
+                >
+                  <div class="message-bubble queued-bubble">
+                    <div class="queued-badge">Queued</div>
+                    <div class="message-content">{{ q.content }}</div>
+                  </div>
+                </div>
+                <div class="queued-clear-row">
+                  <button class="queued-clear-btn" @click="store.clearQueue()" aria-label="Cancel queued messages">
+                    Cancel {{ store.queuedMessages.length }} queued
+                  </button>
+                </div>
+              </template>
 
               <p
                 v-if="!store.currentConversation.messages.length && !store.streaming"
@@ -1610,29 +1622,36 @@ details[open] .thinking-summary::before {
   }
 }
 
-.queued-indicator {
-  display: flex;
-  align-items: center;
-  gap: 0.4rem;
-  font-size: 0.8rem;
+.queued-bubble {
+  background: var(--color-bg-secondary) !important;
+  border: 1px dashed var(--color-border) !important;
+  opacity: 0.7;
+}
+.queued-badge {
+  font-size: 0.7rem;
+  font-weight: 700;
+  text-transform: uppercase;
+  letter-spacing: 0.05em;
   color: var(--color-text-muted);
-  padding: 0.3rem 1rem;
-  margin: 0.25rem 0;
+  margin-bottom: 0.25rem;
 }
-.queued-icon {
-  font-size: 0.75rem;
+.queued-clear-row {
+  display: flex;
+  justify-content: flex-end;
+  padding-right: 0.5rem;
 }
-.queued-cancel {
+.queued-clear-btn {
   background: none;
-  border: none;
+  border: 1px solid var(--color-border);
+  border-radius: var(--radius-sm, 6px);
   cursor: pointer;
   color: var(--color-text-muted);
-  font-size: 1rem;
-  line-height: 1;
-  padding: 0 0.2rem;
-  margin-left: 0.1rem;
+  font-size: 0.78rem;
+  padding: 0.2rem 0.6rem;
+  font-family: inherit;
 }
-.queued-cancel:hover {
-  color: var(--color-text);
+.queued-clear-btn:hover {
+  color: var(--color-danger, #e74c3c);
+  border-color: var(--color-danger, #e74c3c);
 }
 </style>
diff --git a/frontend/src/views/WorkspaceView.vue b/frontend/src/views/WorkspaceView.vue
index 79c09aa..8ccad75 100644
--- a/frontend/src/views/WorkspaceView.vue
+++ b/frontend/src/views/WorkspaceView.vue
@@ -318,12 +318,24 @@ onUnmounted(async () => {
             </div>
           </div>
 
-          <!-- Queued message indicator -->
-          <div v-if="chatStore.queuedCount" class="queued-indicator">
-            <span>⏳</span>
-            {{ chatStore.queuedCount }} message{{ chatStore.queuedCount > 1 ? 's' : '' }} queued
-            <button class="queued-cancel" @click="chatStore.clearQueue()" aria-label="Cancel queued messages">×</button>
-          </div>
+          <!-- Queued messages — shown as pending bubbles -->
+          <template v-if="chatStore.queuedMessages.length">
+            <div
+              v-for="(q, i) in chatStore.queuedMessages"
+              :key="`queued-${i}`"
+              class="ws-message role-user queued-message"
+            >
+              <div class="message-bubble queued-bubble">
+                <div class="queued-badge">Queued</div>
+                <div class="message-content">{{ q.content }}</div>
+              </div>
+            </div>
+            <div class="queued-clear-row">
+              <button class="queued-clear-btn" @click="chatStore.clearQueue()" aria-label="Cancel queued messages">
+                Cancel {{ chatStore.queuedMessages.length }} queued
+              </button>
+            </div>
+          </template>
 
           <p
             v-if="chatStore.currentConversation && !chatStore.currentConversation.messages.length && !chatStore.streaming"
@@ -631,25 +643,36 @@ details[open] .thinking-summary::before {
   max-height: 300px;
   overflow-y: auto;
 }
-.queued-indicator {
-  display: flex;
-  align-items: center;
-  gap: 0.4rem;
-  font-size: 0.8rem;
-  color: var(--color-text-muted);
-  padding: 0.3rem 0.75rem;
-  margin: 0.25rem 0;
+.queued-bubble {
+  background: var(--color-bg-secondary) !important;
+  border: 1px dashed var(--color-border) !important;
+  opacity: 0.7;
 }
-.queued-cancel {
+.queued-badge {
+  font-size: 0.7rem;
+  font-weight: 700;
+  text-transform: uppercase;
+  letter-spacing: 0.05em;
+  color: var(--color-text-muted);
+  margin-bottom: 0.25rem;
+}
+.queued-clear-row {
+  display: flex;
+  justify-content: flex-end;
+  padding-right: 0.5rem;
+}
+.queued-clear-btn {
   background: none;
-  border: none;
+  border: 1px solid var(--color-border);
+  border-radius: var(--radius-sm, 6px);
   cursor: pointer;
   color: var(--color-text-muted);
-  font-size: 1rem;
-  line-height: 1;
-  padding: 0 0.2rem;
+  font-size: 0.78rem;
+  padding: 0.2rem 0.6rem;
+  font-family: inherit;
 }
-.queued-cancel:hover {
-  color: var(--color-text);
+.queued-clear-btn:hover {
+  color: var(--color-danger, #e74c3c);
+  border-color: var(--color-danger, #e74c3c);
 }
 </style>
diff --git a/src/fabledassistant/services/tools.py b/src/fabledassistant/services/tools.py
index e8bccba..5817d7d 100644
--- a/src/fabledassistant/services/tools.py
+++ b/src/fabledassistant/services/tools.py
@@ -823,7 +823,7 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
             near, ratio = _fuzzy_title_match(task_title, candidates)
             if near is not None:
                 item_type = "task" if near.status is not None else "note"
-                return {"success": False, "error": f"A {item_type} with a very similar title '{near.title}' already exists (id: {near.id}, similarity: {ratio:.0%}). Use update_note to modify it instead of creating a duplicate."}
+                return {"success": False, "requires_confirmation": True, "similar_note": {"id": near.id, "title": near.title}, "error": f"A {item_type} with a very similar title '{near.title}' already exists (similarity: {ratio:.0%}). Ask the user to confirm before creating a separate entry."}
 
             if not arguments.get("confirmed") and len(task_body.strip()) >= 80:
                 from fabledassistant.services.embeddings import semantic_search_notes as _ssn
@@ -832,7 +832,7 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
                 if sem_hits:
                     best_score, best_note = sem_hits[0]
                     item_type = "task" if best_note.status is not None else "note"
-                    return {"success": False, "requires_confirmation": True, "error": f"A {item_type} with very similar content exists: '{best_note.title}' (id: {best_note.id}, semantic similarity: {best_score:.0%}). Ask the user: 'An existing {item_type} covers very similar ground. Shall I still create a separate task titled \"{task_title}\"?' Then retry with confirmed=true if they agree."}
+                    return {"success": False, "requires_confirmation": True, "similar_note": {"id": best_note.id, "title": best_note.title}, "error": f"A {item_type} with very similar content exists: '{best_note.title}' (semantic similarity: {best_score:.0%}). Ask the user to confirm before creating a separate entry."}
 
             note = await create_note(
                 user_id=user_id,
@@ -901,7 +901,7 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
             near, ratio = _fuzzy_title_match(note_title, candidates)
             if near is not None:
                 item_type = "task" if near.status is not None else "note"
-                return {"success": False, "error": f"A {item_type} with a very similar title '{near.title}' already exists (id: {near.id}, similarity: {ratio:.0%}). Use update_note to modify it instead of creating a duplicate."}
+                return {"success": False, "requires_confirmation": True, "similar_note": {"id": near.id, "title": near.title}, "error": f"A {item_type} with a very similar title '{near.title}' already exists (similarity: {ratio:.0%}). Ask the user to confirm before creating a separate entry."}
 
             if not arguments.get("confirmed") and len(note_body.strip()) >= 80:
                 from fabledassistant.services.embeddings import semantic_search_notes as _ssn
@@ -910,7 +910,7 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
                 if sem_hits:
                     best_score, best_note = sem_hits[0]
                     item_type = "task" if best_note.status is not None else "note"
-                    return {"success": False, "requires_confirmation": True, "error": f"A {item_type} with very similar content exists: '{best_note.title}' (id: {best_note.id}, semantic similarity: {best_score:.0%}). Ask the user: 'An existing {item_type} covers very similar ground. Shall I still create a separate note titled \"{note_title}\"?' Then retry with confirmed=true if they agree."}
+                    return {"success": False, "requires_confirmation": True, "similar_note": {"id": best_note.id, "title": best_note.title}, "error": f"A {item_type} with very similar content exists: '{best_note.title}' (semantic similarity: {best_score:.0%}). Ask the user to confirm before creating a separate entry."}
 
             note = await create_note(
                 user_id=user_id,