diff --git a/backup-to-drive.sh b/backup-to-drive.sh
index f4f4a6f..ba5d4bc 100755
--- a/backup-to-drive.sh
+++ b/backup-to-drive.sh
@@ -112,6 +112,7 @@ if [ -z "$MISSING" ]; then
   say "✓ Drive already has every NAS backup — nothing to do"
 else
   FAILED=0
+  OVERDUE=""
   COUNT="$(echo "$MISSING" | wc -l | tr -d ' ')"
   say "$COUNT missing from Drive; copying up to $MAX_PER_RUN"
   n=0
@@ -119,7 +120,16 @@ else
     [ -z "$f" ] && continue
     n=$((n+1)); [ $n -gt $MAX_PER_RUN ] && { say "· stopping at $MAX_PER_RUN this run"; break; }
     TMP="$(mktemp -t checklist-backup)"; OUT="$(mktemp -t checklist-backup-json)"
-    run_remote "cat $REMOTE_DIR/$f" > "$TMP"
+    # Retried, because the fetch is the fragile part. Each of these files is ~275 KB and it
+    # comes back through an expect pseudo-terminal, which does line discipline and has finite
+    # buffers — so a capture occasionally arrives truncated and fails to parse. That is a
+    # transport hiccup, not a corrupt backup: every file that failed this way between
+    # 2026-09-29 and 2026-10-07 copied cleanly on a later night. Retrying in the same run
+    # turns a nightly email into a non-event.
+    ok=0
+    for try in 1 2 3; do
+      : > "$TMP"
+      run_remote "cat $REMOTE_DIR/$f" > "$TMP"
     # expect echoes its own `spawn …` banner and the password prompt onto stdout before the
     # file's contents, so the capture is never pure JSON. Slice from the first { to the last }
     # and only then validate — a truncated or half-read file that *looks* like a backup is
@@ -133,12 +143,27 @@ else
         if(!Array.isArray(j.lists)) process.exit(1);   // shape check, not just valid JSON
         fs.writeFileSync(process.argv[2], JSON.stringify(j));
       ' "$TMP" "$OUT" 2>/dev/null; then
+        ok=1; break
+      fi
+      [ "$try" -lt 3 ] && say "  · $f — incomplete capture (attempt $try), retrying"
+      sleep 3
+    done
+
+    if [ "$ok" = 1 ]; then
       mv "$OUT" "$DRIVE_DIR/$f"; rm -f "$TMP"
       say "  ✓ $f ($(du -k "$DRIVE_DIR/$f" | cut -f1) KB)"
     else
       rm -f "$TMP" "$OUT"
       FAILED=$((FAILED+1))
-      say "  ✗ $f — no valid checklist JSON in the response, skipped"
+      say "  ✗ $f — no valid checklist JSON after 3 attempts, skipped"
+      # Severity depends on the file's AGE, not on this run. Today's backup failing is a
+      # retry tomorrow; one still missing days later means the retries are not working.
+      FDATE="$(printf '%s' "$f" | sed -E 's/^checklists-([0-9]{4}-[0-9]{2}-[0-9]{2})\.json$/\1/')"
+      FEPOCH="$(date -j -f "%Y-%m-%d" "$FDATE" +%s 2>/dev/null || echo 0)"
+      if [ "$FEPOCH" -gt 0 ]; then
+        FAGE=$(( ( $(date +%s) - FEPOCH ) / 86400 ))
+        [ "$FAGE" -gt "$STALE_DAYS" ] && OVERDUE="$OVERDUE$f ($FAGE days old)"$'\n'
+      fi
     fi
   done <<< "$MISSING"
 fi
@@ -171,10 +196,18 @@ say "✓ done — $TOTAL copies off-site, newest ${NEWEST:-none}"
 
 # Some files were fetched but were not usable. The run "succeeded" in the sense that it did
 # not crash, which is exactly the kind of success that hides a broken backup.
-if [ "${FAILED:-0}" -gt 0 ]; then
-  alert "$FAILED backup file(s) could not be copied" \
-        "The run finished, but $FAILED file(s) came back without valid checklist JSON and
-were skipped. See the log for which ones."
+# Only files that are genuinely overdue raise mail. A fetch that fails tonight and succeeds
+# tomorrow is noise, and nightly noise is how an alert stops being read — which is the whole
+# failure mode this script exists to prevent.
+if [ -n "${OVERDUE:-}" ]; then
+  alert "backup file(s) still missing off-site after several days" \
+        "These NAS backups have failed to copy for more than $STALE_DAYS days, so the
+retries are not recovering on their own:
+
+$OVERDUE
+Log: $LOG"
+elif [ "${FAILED:-0}" -gt 0 ]; then
+  say "($FAILED file(s) failed this run but are recent — they will be retried tomorrow, not alerting)"
 fi
 
 # The check that would have caught both of the incidents in the header comment. Every