diff --git a/docs/adr/0009-confirmation-threshold-write-time-backfill.md b/docs/adr/0009-confirmation-threshold-write-time-backfill.md
index ed201849..455369ca 100644
--- a/docs/adr/0009-confirmation-threshold-write-time-backfill.md
+++ b/docs/adr/0009-confirmation-threshold-write-time-backfill.md
@@ -8,6 +8,8 @@ Damping happens at **write time**, not read time. The rejected alternative — r
 
 The flip is **retroactive**, not forward-only. Forward-only (first N−1 failing samples stay `UP` forever, `DOWN` begins at confirmation) is simpler — history would stay append-only — but it systematically shaves N−1 minutes off the front of every real outage, permanently flattering uptime and misreporting outage start times. Retroactive backfill rewrites a bounded window (at most threshold−1 rows, one `UPDATE`) at the moment of crossing; it also makes the threshold compose with the alert Failure Threshold by `max` rather than `+`, because once backfilled the alert lookback sees N consecutive confirmed rows immediately. The cost accepted: `monitoring_data` is no longer append-only over the pending window, so the last-value cache and any reader that observed those rows mid-window saw the pre-flip side until convergence.
 
+A held (pending) row keeps the check's real measured latency and observed error text — no diagnostic information is discarded — tagged with `| Status held during grace period`. On confirmation the backfill preserves that text and appends `| Down confirmed after N consecutive checks` (rather than overwriting it); a confirmed recovery clears the error, since the row becomes the UP side. `raw_status` remains the canonical record of what each check observed.
+
 Deliberately accepted boundaries, chosen for one uniform rule rather than special cases:
 
 - **Count, not minutes.** The threshold is consecutive observations, well-defined for any cron, matching the alerting thresholds' unit; for the common every-minute cron, count and minutes coincide.
diff --git a/src/lib/server/db/repositories/monitoring.ts b/src/lib/server/db/repositories/monitoring.ts
index 3e12b3b8..9a5decf4 100644
--- a/src/lib/server/db/repositories/monitoring.ts
+++ b/src/lib/server/db/repositories/monitoring.ts
@@ -362,14 +362,45 @@ export class MonitoringRepository extends BaseRepository {
     message: string | null,
   ): Promise<number> {
     if (timestamps.length === 0) return 0;
-    return await this.knex("monitoring_data")
+
+    // Recovery (confirmed UP): rows become the UP side — clear any held error text in one update.
+    if (message === null) {
+      return await this.knex("monitoring_data")
+        .where("monitor_tag", monitor_tag)
+        .whereIn("timestamp", timestamps)
+        .whereNotNull("raw_status")
+        .update({
+          status: this.knex.ref("raw_status"),
+          error_message: null,
+        });
+    }
+
+    // Confirmed unhealthy: set each row's status from its observed raw_status and APPEND the
+    // confirmation note to the existing error text (preserving the observed failure reason).
+    // Done per-row for portable string concatenation (|| vs CONCAT differ across SQLite/PG/MySQL)
+    // and to stay idempotent if the backfill is ever replayed.
+    const rows = await this.knex("monitoring_data")
+      .select("timestamp", "error_message", "raw_status")
       .where("monitor_tag", monitor_tag)
       .whereIn("timestamp", timestamps)
-      .whereNotNull("raw_status")
-      .update({
-        status: this.knex.ref("raw_status"),
-        error_message: message,
-      });
+      .whereNotNull("raw_status");
+
+    let updated = 0;
+    for (const row of rows) {
+      const existing: string | null = row.error_message;
+      let nextMessage: string;
+      if (!existing) {
+        nextMessage = message;
+      } else if (existing.indexOf(message) !== -1) {
+        nextMessage = existing; // already appended — keep idempotent
+      } else {
+        nextMessage = `${existing} | ${message}`;
+      }
+      updated += await this.knex("monitoring_data")
+        .where({ monitor_tag, timestamp: row.timestamp })
+        .update({ status: row.raw_status, error_message: nextMessage });
+    }
+    return updated;
   }
 
   async updateMonitoringData(
diff --git a/src/lib/server/queues/monitorExecuteQueue.ts b/src/lib/server/queues/monitorExecuteQueue.ts
index 579e7ea1..52db457d 100644
--- a/src/lib/server/queues/monitorExecuteQueue.ts
+++ b/src/lib/server/queues/monitorExecuteQueue.ts
@@ -140,10 +140,13 @@ const addWorker = () => {
         });
         realtimeData[ts].status = resolved.status;
         if (resolved.pendingHold) {
-          // Hold the confirmed side for display, but keep the real measured latency — zeroing it
-          // would lose data and dent the latency chart during every grace window. Only the error
-          // text is dropped so a held row never shows a status-contradicting failure message.
-          delete realtimeData[ts].error_message;
+          // Hold the confirmed side for display, but PRESERVE the observed latency and error text —
+          // no diagnostic info is discarded. Tag the row to record that the status is being held
+          // during the grace period; on confirmation the backfill appends the confirmation note (#756).
+          const observedError = realtimeData[ts].error_message;
+          realtimeData[ts].error_message = observedError
+            ? `${observedError} | Status held during grace period`
+            : "Status held during grace period";
         }
       }
     }