diff --git a/FEEDBACK.md b/FEEDBACK.md
index 9580c7a..c73e286 100644
--- a/FEEDBACK.md
+++ b/FEEDBACK.md
@@ -699,3 +699,15 @@
 - **Status:** done
 - **Completed:** 2026-02-13 — commit `84512b1`
 - **Description:** Avatar image shows as broken for some deployments. Bardak's instance (deployed by Pelouse) shows a broken image. Works on Nicolas's instance. Likely the avatar URL configured by Pelouse is invalid or blocked. PinchChat should handle broken avatar images gracefully (fallback to initials or default icon).
+
+## Item #67
+- **Date:** 2026-02-13
+- **Priority:** medium
+- **Status:** pending
+- **Description:** Add an update indicator next to the version number in the UI. When a newer Docker image/release is available on GitHub (compare current version vs latest GitHub release tag), show a visual indicator (badge, dot, or link) so users know they can update.
+
+## Item #68
+- **Date:** 2026-02-13
+- **Priority:** high
+- **Status:** pending
+- **Description:** Cursor desync in textarea STILL present after v1.39.2 fix. The cursor position still gets ahead of where characters actually appear. The previous fix (removing padding/bold from backdrop tokens) was insufficient. Need deeper investigation — likely the HighlightedTextarea backdrop and textarea have mismatched rendering (font metrics, line-height, word-wrap differences, or span wrapping in the backdrop creating different text flow). Consider disabling highlight entirely as test, or ensuring backdrop uses identical character-level rendering with zero extra styling that could affect text width/flow.
diff --git a/src/components/Sidebar.tsx b/src/components/Sidebar.tsx
index efaa924..2eb4e38 100644
--- a/src/components/Sidebar.tsx
+++ b/src/components/Sidebar.tsx
@@ -1,10 +1,33 @@
 import { useState, useMemo, useRef, useEffect, useCallback } from 'react';
-import { X, Sparkles, Search, Pin, Trash2, Columns2, Clock, Bot, MessageSquare, Globe, Zap } from 'lucide-react';
+import { X, Sparkles, Search, Pin, Trash2, Columns2, Clock, Bot, MessageSquare, Globe, Zap, ArrowUpCircle } from 'lucide-react';
 import type { Session } from '../types';
 import { useT } from '../hooks/useLocale';
 import { SessionIcon } from './SessionIcon';
 import { sessionDisplayName } from '../lib/sessionName';
 import { relativeTime } from '../lib/relativeTime';
+import { useUpdateCheck } from '../hooks/useUpdateCheck';
+
+function VersionBadge() {
+  const update = useUpdateCheck(__APP_VERSION__);
+  if (update.available) {
+    return (
+      <a
+        href={update.releaseUrl || '#'}
+        target="_blank"
+        rel="noopener noreferrer"
+        className="ml-1 inline-flex items-center gap-1 text-[9px] text-emerald-400 hover:text-emerald-300 transition-colors"
+        title={`Update available: v${update.latestVersion}`}
+      >
+        <span className="text-pc-text-faint line-through select-all">v{__APP_VERSION__}</span>
+        <ArrowUpCircle size={10} />
+        <span>v{update.latestVersion}</span>
+      </a>
+    );
+  }
+  return (
+    <span className="ml-1 text-[9px] text-pc-text-faint select-all" title={`PinchChat v${__APP_VERSION__}`}>v{__APP_VERSION__}</span>
+  );
+}
 
 const PINNED_KEY = 'pinchchat-pinned-sessions';
 const WIDTH_KEY = 'pinchchat-sidebar-width';
@@ -490,7 +513,7 @@ export function Sidebar({ sessions, activeSession, onSwitch, onDelete, onSplit,
           <span className="h-1.5 w-1.5 rounded-full bg-violet-300/60 shadow-[0_0_10px_rgba(168,85,247,0.5)]" />
           <span className="h-1.5 w-1.5 rounded-full bg-[var(--pc-accent-dim)] shadow-[0_0_10px_rgba(34,211,238,0.5)]" />
           <span className="h-1.5 w-1.5 rounded-full bg-indigo-300/50 shadow-[0_0_10px_rgba(99,102,241,0.4)]" />
-          <span className="ml-1 text-[9px] text-pc-text-faint select-all" title={`PinchChat v${__APP_VERSION__}`}>v{__APP_VERSION__}</span>
+          <VersionBadge />
         </div>
         {/* Resize drag handle */}
         <div
diff --git a/src/hooks/useUpdateCheck.ts b/src/hooks/useUpdateCheck.ts
new file mode 100644
index 0000000..5b1239b
--- /dev/null
+++ b/src/hooks/useUpdateCheck.ts
@@ -0,0 +1,65 @@
+import { useState, useEffect } from 'react';
+
+const GITHUB_API = 'https://api.github.com/repos/MarlBurroW/pinchchat/releases/latest';
+const CHECK_INTERVAL = 60 * 60 * 1000; // 1 hour
+const CACHE_KEY = 'pinchchat-latest-version';
+
+interface UpdateInfo {
+  available: boolean;
+  latestVersion: string | null;
+  releaseUrl: string | null;
+}
+
+export function useUpdateCheck(currentVersion: string): UpdateInfo {
+  const [info, setInfo] = useState<UpdateInfo>({ available: false, latestVersion: null, releaseUrl: null });
+
+  useEffect(() => {
+    let timeout: ReturnType<typeof setTimeout>;
+
+    async function check() {
+      try {
+        // Check cache first
+        const cached = localStorage.getItem(CACHE_KEY);
+        if (cached) {
+          const { version, url, ts } = JSON.parse(cached);
+          if (Date.now() - ts < CHECK_INTERVAL) {
+            if (version && isNewer(version, currentVersion)) {
+              setInfo({ available: true, latestVersion: version, releaseUrl: url });
+            }
+            timeout = setTimeout(check, CHECK_INTERVAL - (Date.now() - ts));
+            return;
+          }
+        }
+
+        const res = await fetch(GITHUB_API, { headers: { Accept: 'application/vnd.github.v3+json' } });
+        if (!res.ok) return;
+        const data = await res.json();
+        const tag: string = data.tag_name?.replace(/^v/, '') || '';
+        const url: string = data.html_url || '';
+
+        localStorage.setItem(CACHE_KEY, JSON.stringify({ version: tag, url, ts: Date.now() }));
+
+        if (tag && isNewer(tag, currentVersion)) {
+          setInfo({ available: true, latestVersion: tag, releaseUrl: url });
+        }
+      } catch { /* silent */ }
+      timeout = setTimeout(check, CHECK_INTERVAL);
+    }
+
+    check();
+    return () => clearTimeout(timeout);
+  }, [currentVersion]);
+
+  return info;
+}
+
+/** True if remote is newer than local (semver compare) */
+function isNewer(remote: string, local: string): boolean {
+  const r = remote.split('.').map(Number);
+  const l = local.split('.').map(Number);
+  for (let i = 0; i < 3; i++) {
+    if ((r[i] || 0) > (l[i] || 0)) return true;
+    if ((r[i] || 0) < (l[i] || 0)) return false;
+  }
+  return false;
+}
diff --git a/src/index.css b/src/index.css
index 5c711c0..a947ca8 100644
--- a/src/index.css
+++ b/src/index.css
@@ -212,11 +212,12 @@ html, body {
 
 .ht-backdrop,
 .ht-textarea {
-  /* Must share identical text layout */
+  /* Must share EXACTLY identical text layout — any difference causes cursor desync */
   font-family: inherit;
-  font-size: 0.875rem; /* text-sm */
-  line-height: 1.25rem;
-  padding: 0.75rem 1rem; /* py-3 px-4 */
+  font-size: inherit;
+  line-height: inherit;
+  letter-spacing: inherit;
+  word-spacing: inherit;
   white-space: pre-wrap;
   word-break: break-word;
   overflow-wrap: break-word;
@@ -224,6 +225,7 @@ html, body {
   overflow-y: auto;
   margin: 0;
   box-sizing: border-box;
+  /* padding, border, border-radius all come from the shared className */
 }
 
 .ht-backdrop {
@@ -231,9 +233,7 @@ html, body {
   inset: 0;
   pointer-events: none;
   color: var(--pc-text-primary);
-  border: 1px solid transparent; /* match textarea border width to keep text aligned */
-  border-radius: 1rem; /* rounded-2xl */
-  max-height: 200px;
+  background: transparent;
 }
 
 .ht-textarea {
@@ -246,38 +246,31 @@ html, body {
   z-index: 1;
 }
 
-/* Token colors */
+/* Token colors — ONLY color allowed, nothing that changes text geometry */
 .ht-code-block {
   color: #67e8f9; /* cyan-300 */
-  background: var(--pc-accent-glow);
-  border-radius: 4px;
 }
 
 .ht-inline-code {
   color: #67e8f9;
-  background: var(--pc-accent-glow);
-  border-radius: 3px;
-  /* No padding — must match textarea text layout exactly to avoid cursor desync */
 }
 
 .ht-bold {
   color: var(--pc-text-primary);
-  /* No font-weight change — bold text is wider and causes cursor desync */
 }
 
 .ht-italic {
   color: var(--pc-text-secondary);
-  font-style: italic;
+  /* No font-style: italic — italic glyphs have different widths, causes cursor desync */
 }
 
 .ht-heading {
   color: #a78bfa; /* violet-400 */
-  font-weight: 600;
+  /* No font-weight — bolder glyphs are wider, causes cursor desync */
 }
 
 .ht-link {
   color: #67e8f9;
-  text-decoration: underline;
 }
 
 /* Accessibility: respect reduced-motion preferences */