diff --git a/packages/extension/src/background/index.ts b/packages/extension/src/background/index.ts
index 74f0772..b43ad29 100644
--- a/packages/extension/src/background/index.ts
+++ b/packages/extension/src/background/index.ts
@@ -201,6 +201,12 @@
 browser.action.onClicked.addListener(async (tab) => {
   if (tab.id == null) return;
   try {
+    // first run: the toolbar click takes you to settings instead of the picker
+    const settings = await getSettings();
+    if (!settings.token || !settings.defaultProjectId) {
+      await browser.runtime.openOptionsPage();
+      return;
+    }
     await startPicker(tab.id);
   } catch (error) {
     console.error("[ltt] failed to start picker:", error);
@@ -332,6 +338,11 @@
       return { ok: true, data: { stepCount: buffer.events.length } };
     }
 
+    case "open_options": {
+      await browser.runtime.openOptionsPage();
+      return { ok: true };
+    }
+
     case "list_projects": {
       try {
         const client = await getHttpClient();
diff --git a/packages/extension/src/content/overlay/NoteComposer.vue b/packages/extension/src/content/overlay/NoteComposer.vue
index ef87f32..f2cf10a 100644
--- a/packages/extension/src/content/overlay/NoteComposer.vue
+++ b/packages/extension/src/content/overlay/NoteComposer.vue
@@ -23,6 +23,8 @@
 const submitting = ref(false);
 const error = ref<string | null>(null);
 const titleInput = ref<HTMLInputElement>();
+/** null = checked and fine; string = what the user must fix in settings first */
+const settingsProblem = ref<string | null>(null);
 
 onMounted(() => {
   titleInput.value?.focus();
@@ -31,6 +33,18 @@
 });
 
 onMounted(async () => {
+  const settings = (await browser.runtime.sendMessage({ type: "settings_get" })) as {
+    ok: boolean;
+    data?: { token: string | null; defaultProjectId: string | null };
+  };
+  if (!settings?.data?.token) {
+    settingsProblem.value = "Not signed in — open the extension settings to log in";
+  } else if (!settings.data.defaultProjectId) {
+    settingsProblem.value = "No default project selected — open the extension settings";
+  }
+});
+
+onMounted(async () => {
   const response = (await browser.runtime.sendMessage({ type: "capture" })) as {
     ok: boolean;
     data?: { dataUrl: string };
@@ -104,6 +118,10 @@
   }
 }
 
+async function openSettings() {
+  await browser.runtime.sendMessage({ type: "open_options" }).catch(() => {});
+}
+
 function onKeyDown(event: KeyboardEvent) {
   if (event.key === "Escape") {
     event.preventDefault();
@@ -130,6 +148,14 @@
         </button>
       </div>
 
+      <div v-if="settingsProblem" class="composer-warn">
+        <i class="ph ph-warning" />
+        <span>{{ settingsProblem }}</span>
+        <button type="button" class="composer-btn composer-btn-warn" @click="openSettings">
+          Open settings
+        </button>
+      </div>
+
       <div v-if="screenshot" class="composer-screenshot">
         <AnnotationEditor :src="screenshot" v-model:shapes="shapes" editable />
       </div>
@@ -254,6 +280,23 @@
   color: var(--color-danger, #f7768e);
   font-size: 12px;
 }
+.composer-warn {
+  display: flex;
+  align-items: center;
+  gap: 8px;
+  padding: 8px 10px;
+  border: 2px solid var(--color-warning, #e0af68);
+  color: var(--color-warning, #e0af68);
+  font-size: 12px;
+  text-transform: none;
+  letter-spacing: normal;
+}
+.composer-btn-warn {
+  margin-left: auto;
+  background: transparent;
+  color: inherit;
+  border-color: var(--color-warning, #e0af68);
+}
 .composer-actions {
   display: flex;
   justify-content: flex-end;