diff --git a/kubernetes/clusters/homelab/uptime-monitor.yaml b/kubernetes/clusters/homelab/uptime-monitor.yaml
index 395c29cd..5cb02c08 100644
--- a/kubernetes/clusters/homelab/uptime-monitor.yaml
+++ b/kubernetes/clusters/homelab/uptime-monitor.yaml
@@ -71,12 +71,85 @@ spec:
   # Kustomization would report a CEL evaluation error rather than a clean
   # in-progress.
   #
-  # No `inProgress` expression: Flux treats "neither failed nor current" as
-  # in-progress, which is the behaviour wanted here.
+  # `failed` NAMES THE TWO REASONS ESO STOPS RETRYING ON, AND DELIBERATELY LEAVES
+  # OUT `SecretSyncedError` (REN-106). The first cut of this block fired on any
+  # `Ready=False` at all, and that path is undampened: the `flux-failures` Alert
+  # (infrastructure/flux-notifications/alerts.yaml) forwards error events from
+  # every Kustomization to Alertmanager, and a Flux health check has no `for:`
+  # window, so a single bad poll would have mailed the owner.
+  #
+  # Read off the ESO the cluster actually runs, v2.11.0 (the chart range
+  # `>=2.7.0 <3.0.0` in infrastructure/external-secrets/helmrelease.yaml resolves
+  # there today). On the Secret target path ESO sets `Ready=False` with exactly
+  # three reasons, and what separates them is whether it intends to try again
+  # (pkg/controllers/externalsecret/externalsecret_controller.go):
+  #   SecretSyncedError  — provider read, template or update failed. Almost every
+  #                        site returns the error, so controller-runtime requeues
+  #                        with backoff. This is the reason an OpenBao blip, a
+  #                        token renewal AND a not-yet-populated key all produce —
+  #                        the transient case and the REN-100 case share one
+  #                        string, so the string cannot tell them apart.
+  #   SecretOwnedByOther — the target Secret is owned by something else.
+  #   SecretImmutable    — the target Secret is immutable and needs an update.
+  # The last two return `nil`, commented in ESO's own source as "cant be fixed by
+  # retrying": ESO has given up, nothing is in flight, so failing at once is
+  # correct and cannot be a flap. Narrowing to `reason == 'SecretSyncedError'`
+  # instead — REN-106's first suggestion — would have inverted that, keeping the
+  # one flap-prone reason and dropping the two that cannot flap.
+  #
+  # Two details that make `failed` an allowlist of reasons rather than the
+  # complement of `SecretSyncedError`: one `SecretSyncedError` site
+  # (`ErrSecretSetCtrlRef`) also returns `nil`, so that string is not a reliable
+  # "still trying" signal either way; and the generic-target path (`spec.target`
+  # pointing at something other than a Secret) has its own reason set,
+  # `ResourceSyncedError`, which is not used here — this ExternalSecret targets a
+  # Secret — and is left to the in-progress path if it ever is.
+  #
+  # A `SecretSyncedError` is dampened, not dropped: it matches neither
+  # expression, so Flux reports in-progress and keeps polling until `timeout: 5m`
+  # above expires and the Kustomization fails. That timeout is the `for:` window
+  # this path otherwise has none of — a blip that clears inside it never reaches
+  # the owner, a sync that is genuinely stuck still does, about five minutes
+  # later.
+  #
+  # EVERY SHAPE AN ExternalSecret STATUS CAN TAKE GETS A VERDICT FROM THE TWO
+  # EXPRESSIONS BELOW. There are three, not two, and the third one — no `Ready`
+  # condition at all — is the one a reader is most likely to miss:
+  #
+  #   1. no conditions yet (applied, first reconcile unfinished): the `has()`
+  #      guard makes both expressions false -> in-progress, bounded by
+  #      `timeout: 5m`.
+  #   2. `Ready=True`: `current` -> Current. Note this includes reasons
+  #      `SecretDeleted` and `SecretMissing`, which ESO reports as Ready=True
+  #      (markAsDone) even though no target Secret exists. Reaching them needs
+  #      `deletionPolicy: Delete`/`Merge` or `creationPolicy: Merge`; this
+  #      ExternalSecret takes the defaults (Retain/Owner), where a vanished
+  #      provider key is a `SecretSyncedError` instead. Anyone who later sets
+  #      either policy here reopens REN-100 through this expression.
+  #   3. `Ready=False`: `failed` for the two non-retrying reasons above,
+  #      in-progress for the rest.
+  #
+  # No `inProgress` expression: only `apiVersion` and `current` are required by
+  # the CRD (flux-system/gotk-components.yaml, kustomize-controller v1.9.5), and
+  # Flux evaluates inProgress -> failed -> current and returns in-progress when
+  # nothing matches (fluxcd/pkg runtime/cel, StatusEvaluator.Evaluate). An
+  # `inProgress` naming shapes 1 and 3 would therefore be a no-op on all three.
+  #
+  # "conditions present but no `Ready` condition" is NOT a fourth shape (REN-106).
+  # On a live object ESO only ever writes conditions of type `Ready`; the
+  # `Deleted` type is never persisted — it is built on a throwaway object in the
+  # `IsNotFound` branch of Reconcile purely to retire that object's metric series
+  # ("this does not actually set the condition on the ExternalSecret, because it
+  # does not exist"). So `externalsecret_status_condition{condition="Deleted"}`
+  # outlives the object it names, until the ESO pod restarts.
+  # `ai/wiki-index-basic-auth` is that: retired from git in 419cbed3, target
+  # Secret gone from the namespace, sync counter frozen, still a series in an ESO
+  # pod older than the prune. Any alert built on this metric (REN-103) has to
+  # exclude that shape; this health check never sees it.
   healthCheckExprs:
     - apiVersion: external-secrets.io/v1
       kind: ExternalSecret
-      failed: "has(status.conditions) && status.conditions.exists(c, c.type == 'Ready' && c.status == 'False')"
+      failed: "has(status.conditions) && status.conditions.exists(c, c.type == 'Ready' && c.status == 'False' && (c.reason == 'SecretOwnedByOther' || c.reason == 'SecretImmutable'))"
       current: "has(status.conditions) && status.conditions.exists(c, c.type == 'Ready' && c.status == 'True')"
   dependsOn:
     # ESO itself, and the `uptime-monitor` namespace (declared centrally in