diff --git a/hub/internal/api/handler.go b/hub/internal/api/handler.go
index 018f7384..f6e64e05 100644
--- a/hub/internal/api/handler.go
+++ b/hub/internal/api/handler.go
@@ -1271,7 +1271,7 @@ func (h *Handler) handleHostEscrowPut(w http.ResponseWriter, r *http.Request, pa
 	}
 	if superseded {
 		n, _ := h.store.CountSupersededEscrow(pathHostID)
-		h.logger.Printf("[INFO] escrow for host %s superseded a different-passphrase blob — RETAINED (now %d superseded blob(s) held)", pathHostID, n)
+		h.logger.Printf("[INFO] escrow for host %s superseded an escrow with a different passphrase or backup key (R-366) — RETAINED (now %d superseded blob(s) held)", pathHostID, n)
 		// Hub-internal audit event (not gated by allowedEventTypes) — tied to the owning customer.
 		if host, herr := h.store.GetHost(pathHostID); herr == nil && host != nil && host.CustomerID != "" {
 			details, _ := json.Marshal(map[string]any{"host_id": pathHostID, "retained_count": n})
diff --git a/hub/internal/store/r366_escrow_key_change_test.go b/hub/internal/store/r366_escrow_key_change_test.go
new file mode 100644
index 00000000..8b3f6c41
--- /dev/null
+++ b/hub/internal/store/r366_escrow_key_change_test.go
@@ -0,0 +1,65 @@
+package store
+
+import "testing"
+
+// R-366 — a reinstall mints a NEW whole-guest backup key K (`felhom-pbs-apply`: `--encryption-key
+// autogen`) while, since R-241's mint guard, the box keeps its restic password. The escrow PUT then
+// carries the SAME restic sha and a NEW key fingerprint. Until this fix the supersession rule looked
+// at the restic sha only, so the row holding the OLD K (wrapped under the customer's recovery code)
+// was OVERWRITTEN — every whole-guest archive written before the reinstall became unopenable for
+// good, not only for the new box. The old row must be RETAINED when K changes.
+//
+// COMPANION RED-PROOF (observed, `audits/night-burndown-2026-10-06/r366/red-key-change.txt`): on the
+// pre-fix rule (`curSHA != resticPwSHA256` alone) this fails with "a new backup key with the same
+// restic password must supersede (retain the old K)". Restored.
+func TestSaveHostEscrow_R366_NewBackupKeySameResticPasswordRetainsOldKey(t *testing.T) {
+	st := newTestStore(t)
+	const h = "h1"
+	if _, _, err := st.SaveHostEscrow(h, []byte("K-old-wrapped"), "3f:4f:65:c0", "zk", "2026-08-18T00:00:00Z", "SHA_SAME"); err != nil {
+		t.Fatal(err)
+	}
+	sup, _, err := st.SaveHostEscrow(h, []byte("K-new-wrapped"), "dd:d1:d8:53", "zk", "2026-08-21T00:00:00Z", "SHA_SAME")
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !sup {
+		t.Fatal("a new backup key with the same restic password must supersede (retain the old K)")
+	}
+	old, err := st.ListSupersededEscrow(h)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(old) != 1 || string(old[0].Blob) != "K-old-wrapped" || old[0].KeyFingerprint != "3f:4f:65:c0" {
+		t.Fatalf("the old K is not retained: %+v", old)
+	}
+	cur, _ := st.GetHostEscrow(h)
+	if cur == nil || string(cur.Blob) != "K-new-wrapped" || cur.KeyFingerprint != "dd:d1:d8:53" {
+		t.Fatalf("the current row must be the new K: %+v", cur)
+	}
+}
+
+// The same key in another letter case, or a legacy row with no fingerprint, is NOT a key change:
+// a re-upload of the same K must stay idempotent (no retained row per re-ceremony).
+func TestSaveHostEscrow_R366_SameKeyOrUnknownFingerprintDoesNotSupersede(t *testing.T) {
+	st := newTestStore(t)
+	const h = "h1"
+	if _, _, err := st.SaveHostEscrow(h, []byte("a"), "AB:CD", "zk", "2026-08-18T00:00:00Z", "SHA"); err != nil {
+		t.Fatal(err)
+	}
+	for i, fp := range []string{"ab:cd", " AB:CD ", ""} {
+		sup, _, err := st.SaveHostEscrow(h, []byte("b"), fp, "zk", "2026-08-19T00:00:00Z", "SHA")
+		if err != nil {
+			t.Fatal(err)
+		}
+		if sup {
+			t.Fatalf("case %d (%q): the same or an unknown fingerprint must not supersede", i, fp)
+		}
+		// keep the stored fingerprint known for the next case
+		if _, _, err := st.SaveHostEscrow(h, []byte("a"), "AB:CD", "zk", "2026-08-18T00:00:00Z", "SHA"); err != nil {
+			t.Fatal(err)
+		}
+	}
+	if n, _ := st.CountSupersededEscrow(h); n != 0 {
+		t.Fatalf("no key change happened, yet %d rows were retained", n)
+	}
+}
diff --git a/hub/internal/store/store.go b/hub/internal/store/store.go
index af3d4beb..92529c1f 100644
--- a/hub/internal/store/store.go
+++ b/hub/internal/store/store.go
@@ -3257,6 +3257,13 @@ func demoteCurrentEscrowTx(tx *sql.Tx, hostID string) (int64, error) {
 	return res.RowsAffected()
 }
 
+// backupKeyChanged reports whether two key fingerprints name different keys. Case and surrounding
+// space do not count; an empty side is unknown, never a change.
+func backupKeyChanged(cur, next string) bool {
+	cur, next = strings.TrimSpace(cur), strings.TrimSpace(next)
+	return cur != "" && next != "" && !strings.EqualFold(cur, next)
+}
+
 func (s *Store) SaveHostEscrow(hostID string, blob []byte, keyFingerprint, posture, createdAt, resticPwSHA256 string) (superseded bool, prevResticPwSHA256 string, err error) {
 	tx, err := s.db.Begin()
 	if err != nil {
@@ -3269,10 +3276,14 @@ func (s *Store) SaveHostEscrow(hostID string, blob []byte, keyFingerprint, postu
 	}()
 
 	// Retain the current row iff it exists AND seals a DIFFERENT restic password (the incident: a
-	// recreated volume mints a new passphrase; the old must stay recoverable with its recovery code).
-	var curSHA string
+	// recreated volume mints a new passphrase; the old must stay recoverable with its recovery code)
+	// OR a DIFFERENT whole-guest backup key K (R-366: a reinstall mints a new K — `--encryption-key
+	// autogen` — while R-241 keeps the restic password, so the restic sha alone overwrote the only copy
+	// of the old K and every pre-reinstall archive became unopenable for good). An unknown fingerprint
+	// on either side ("" — a legacy row) is not a change. Pinned by TestSaveHostEscrow_R366_*.
+	var curSHA, curFP string
 	var exists bool
-	switch scanErr := tx.QueryRow(`SELECT COALESCE(restic_pw_sha256,'') FROM host_escrow WHERE host_id = ?`, hostID).Scan(&curSHA); scanErr {
+	switch scanErr := tx.QueryRow(`SELECT COALESCE(restic_pw_sha256,''), COALESCE(key_fingerprint,'') FROM host_escrow WHERE host_id = ?`, hostID).Scan(&curSHA, &curFP); scanErr {
 	case nil:
 		exists = true
 	case sql.ErrNoRows:
@@ -3284,7 +3295,7 @@ func (s *Store) SaveHostEscrow(hostID string, blob []byte, keyFingerprint, postu
 	if exists {
 		prevResticPwSHA256 = curSHA // R-197: the caller compares; "" = no row or a legacy hash-less blob
 	}
-	if exists && curSHA != resticPwSHA256 {
+	if exists && (curSHA != resticPwSHA256 || backupKeyChanged(curFP, keyFingerprint)) {
 		if _, err = demoteCurrentEscrowTx(tx, hostID); err != nil {
 			return false, prevResticPwSHA256, err
 		}