diff --git a/apps/docs/.vitepress/theme/Layout.vue b/apps/docs/.vitepress/theme/Layout.vue
index 9976dce3..ba76b08b 100644
--- a/apps/docs/.vitepress/theme/Layout.vue
+++ b/apps/docs/.vitepress/theme/Layout.vue
@@ -16,5 +16,59 @@ const { Layout } = DefaultTheme;
         <GitHubStars />
       </div>
     </template>
+    <template #not-found>
+      <div class="not-found-page">
+        <span class="not-found-otter">🦦</span>
+        <h1 class="not-found-heading">Hello from the otter side!</h1>
+        <p class="not-found-text">This page swam away. Let's get you back on track.</p>
+        <a href="/" class="not-found-link">Back to docs</a>
+      </div>
+    </template>
   </Layout>
 </template>
+
+<style scoped>
+.not-found-page {
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  justify-content: center;
+  min-height: 60vh;
+  text-align: center;
+  padding: 2rem;
+}
+
+.not-found-otter {
+  font-size: 4.5rem;
+}
+
+.not-found-heading {
+  margin-top: 1.5rem;
+  font-size: 2.25rem;
+  font-weight: 700;
+  letter-spacing: -0.02em;
+}
+
+.not-found-text {
+  margin-top: 1rem;
+  font-size: 1.125rem;
+  color: var(--vp-c-text-2);
+}
+
+.not-found-link {
+  margin-top: 2rem;
+  display: inline-block;
+  padding: 0.625rem 1.5rem;
+  border-radius: 0.5rem;
+  background: var(--vp-c-brand-1);
+  color: var(--vp-c-white);
+  font-size: 0.875rem;
+  font-weight: 500;
+  transition: background 0.2s;
+}
+
+.not-found-link:hover {
+  background: var(--vp-c-brand-2);
+  text-decoration: none;
+}
+</style>
diff --git a/apps/landing/src/app/not-found.tsx b/apps/landing/src/app/not-found.tsx
new file mode 100644
index 00000000..89c5fd94
--- /dev/null
+++ b/apps/landing/src/app/not-found.tsx
@@ -0,0 +1,26 @@
+import { Footer } from "@/components/footer";
+import { Navbar } from "@/components/navbar";
+
+export default function NotFound() {
+  return (
+    <>
+      <Navbar />
+      <main className="flex min-h-screen flex-col items-center justify-center px-6 pt-16">
+        <span className="text-7xl">🦦</span>
+        <h1 className="mt-6 text-4xl font-bold tracking-tight sm:text-5xl">
+          Hello from the otter side!
+        </h1>
+        <p className="mt-4 text-lg text-muted">
+          This page swam away. Let&apos;s get you back on track.
+        </p>
+        <a
+          href="/"
+          className="mt-8 rounded-lg bg-accent px-6 py-3 text-sm font-medium text-accent-foreground transition-colors hover:bg-accent-hover"
+        >
+          Back to homepage
+        </a>
+      </main>
+      <Footer />
+    </>
+  );
+}
diff --git a/apps/web/src/App.tsx b/apps/web/src/App.tsx
index a9ca89a1..325a106b 100644
--- a/apps/web/src/App.tsx
+++ b/apps/web/src/App.tsx
@@ -1,7 +1,7 @@
 import { APP_VERSION, en, shouldShowConsent } from "@snapotter/shared";
 import { Component, type ErrorInfo, lazy, type ReactNode, Suspense, useEffect } from "react";
 import { BrowserRouter, Navigate, Route, Routes, useLocation } from "react-router-dom";
-import { Toaster } from "sonner";
+import { Toaster, toast } from "sonner";
 import { ConnectionMonitor } from "./components/common/connection-monitor";
 import { KeyboardShortcutProvider } from "./components/common/keyboard-shortcut-provider";
 import { I18nProvider } from "./contexts/i18n-context";
@@ -186,6 +186,15 @@ export function App() {
     fetchAnalyticsConfig();
   }, [fetchAnalyticsConfig]);
 
+  useEffect(() => {
+    if (localStorage.getItem("snapotter-welcome") === "1") {
+      localStorage.removeItem("snapotter-welcome");
+      toast("Hello from the otter side! 🦦", {
+        duration: 5000,
+      });
+    }
+  }, []);
+
   useEffect(() => {
     if (
       !analyticsConfigLoaded ||
diff --git a/apps/web/src/pages/change-password-page.tsx b/apps/web/src/pages/change-password-page.tsx
index 3a11b314..e00ae94b 100644
--- a/apps/web/src/pages/change-password-page.tsx
+++ b/apps/web/src/pages/change-password-page.tsx
@@ -100,6 +100,7 @@ export function ChangePasswordPage() {
         return;
       }
 
+      localStorage.setItem("snapotter-welcome", "1");
       // Trigger browser password save prompt via real form submission + navigation
       const username = localStorage.getItem("snapotter-username") || "admin";
       triggerBrowserPasswordSave(username, newPassword);
@@ -218,6 +219,7 @@ export function ChangePasswordPage() {
       </div>
       <div className="hidden lg:flex flex-1 bg-primary/90 items-center justify-center p-12 text-white rounded-s-3xl">
         <div className="max-w-lg space-y-6 text-center">
+          <span className="text-7xl">🦦</span>
           <h2 className="text-3xl font-bold">{t.changePassword.sidebarTitle}</h2>
           <p className="text-lg text-white/80">{t.changePassword.sidebarDescription}</p>
         </div>
diff --git a/packages/shared/src/i18n/en.ts b/packages/shared/src/i18n/en.ts
index c1ab02ce..c2eb412b 100644
--- a/packages/shared/src/i18n/en.ts
+++ b/packages/shared/src/i18n/en.ts
@@ -1687,8 +1687,8 @@ export const en = {
     connectionError: "Connection error",
     changingButton: "Changing...",
     changeButton: "Change password",
-    sidebarTitle: "Almost there",
-    sidebarDescription: "Set a strong password to secure your account, then you are good to go.",
+    sidebarTitle: "Hello from the otter side!",
+    sidebarDescription: "Set a strong password to secure your account, then you're good to go.",
   },
   automate: {
     title: "Automate",