diff --git a/main.js b/main.js
index 9632e433..f897bac8 100644
--- a/main.js
+++ b/main.js
@@ -618,21 +618,27 @@ async function checkForUpdate() {
   // newer release on the mirror shows the same one-click "Install & restart"
   // chip as a real install, and that installer targets the REAL install dir.
   // 2026-09-15 a test run reinstalled the user's Theseus that way.
-  if (process.env.THESEUS_NO_UPDATE_CHECK) return;
+  // Returns true when the manifest was read (whatever it said), false when
+  // the check itself failed — the startup scheduler retries on false.
+  if (process.env.THESEUS_NO_UPDATE_CHECK) return true;
+  const t0 = Date.now();
   try {
-    const controller = new AbortController();
-    const to = setTimeout(() => controller.abort(), 5000);
-    const r = await fetch(UPDATE_MANIFEST_URL, { signal: controller.signal, cache: "no-store" });
-    clearTimeout(to);
-    if (!r.ok) return;
+    // 20 s, not 5: the startup check shares the main thread with snapshot
+    // parsing, tab restore and add-on activation. Measured 2026-10-03: 3.2 s
+    // for this fetch on an empty profile, 1.6 s of it the event loop being
+    // busy — a real profile went past 5 s, the abort won, and (the failure
+    // being silent with no retry) the update only appeared after a manual
+    // "Check for updates".
+    const r = await fetch(UPDATE_MANIFEST_URL, { signal: AbortSignal.timeout(20000), cache: "no-store" });
+    if (!r.ok) { console.warn(`[update] manifest HTTP ${r.status}`); return false; }
     const manifest = await r.json();
     const rel = (manifest.releases || []).find((x) => x.id === "theseus-navigator");
-    if (!rel || !rel.version) return;
+    if (!rel || !rel.version) return true;
     if (!versionIsNewer(rel.version, app.getVersion())) {
       // Same version or older — nothing to offer. Clear any stale state so the
       // chip disappears after the user has updated + relaunched.
       if (updateAvailable) { updateAvailable = null; updateDownloadState = "idle"; updateDownloadPath = null; emitUpdateAvailable(); }
-      return;
+      return true;
     }
     const files = rel.files || {};
     const setupFile    = Object.keys(files).find((k) => /Setup/i.test(k));
@@ -647,15 +653,31 @@ async function checkForUpdate() {
     };
     const versionChanged = !updateAvailable || updateAvailable.version !== nextAvailable.version;
     updateAvailable = nextAvailable;
-    if (versionChanged) {
-      // New candidate — reset any prior download state and kick off a fresh
-      // silent background fetch so the chip lands as "ready to install".
+    if (versionChanged || updateDownloadState === "failed") {
+      // New candidate — or the same one whose download failed (truncated,
+      // hash mismatch, network drop), which used to stay failed until the
+      // next release. Reset and kick off a fresh silent background fetch so
+      // the chip lands as "ready to install".
       updateDownloadState = "idle";
       updateDownloadPath = null;
       autoDownloadUpdate();
     }
     emitUpdateAvailable();
-  } catch { /* offline / manifest unreachable — silent */ }
+    return true;
+  } catch (e) {
+    console.warn(`[update] check failed after ${Date.now() - t0} ms: ${e?.name || ""} ${e?.cause?.code || e?.message || e}`);
+    return false;
+  }
+}
+// Startup check: wait for the boot rush to pass, then retry with backoff on
+// failure — a flaky network at launch must not mean "no update until the
+// 6-hourly recheck".
+const UPDATE_STARTUP_DELAYS_MS = [8_000, 30_000, 2 * 60_000, 10 * 60_000, 30 * 60_000];
+function scheduleStartupUpdateCheck(attempt = 0) {
+  if (attempt >= UPDATE_STARTUP_DELAYS_MS.length) return;
+  setTimeout(() => {
+    checkForUpdate().then((ok) => { if (!ok) scheduleStartupUpdateCheck(attempt + 1); }, () => scheduleStartupUpdateCheck(attempt + 1));
+  }, UPDATE_STARTUP_DELAYS_MS[attempt]);
 }
 // Silent background pre-download of the update installer. The user never
 // has to click Download — clicking the chip goes straight to Install.
@@ -1330,7 +1352,7 @@ function onChromeReady() {
   emitUpdateAvailable();
   setTimeout(loadOverlays, 250);
   refreshSnapshotFromSia().catch(() => {});
-  checkForUpdate().catch(() => {});
+  scheduleStartupUpdateCheck();
   refreshRemoteHomeCards().catch(() => {});
 }
 function applyThrottle() {