diff --git a/scripts/upgrade_state.sh b/scripts/upgrade_state.sh
index 2e6e7faa..51fbf5d8 100755
--- a/scripts/upgrade_state.sh
+++ b/scripts/upgrade_state.sh
@@ -445,6 +445,17 @@ collect_k8s() {
 
     K8S_NEXT="$(next_daily_noon_utc)"
 
+    # Failed chain-Job detection. A preflight/phase Job can abort BEFORE pushing
+    # k8s_upgrade_in_flight=1 (the preflight gates exit pre-metric), so in-flight
+    # / stalled stay clean while the pipeline is actually wedged: the
+    # deterministic-name + 7d-TTL Job blocks re-spawn. Surface it directly.
+    # (2026-06-17: a transient critical alert wedged the 1.34.9 preflight for 5
+    # days, invisible to every metric-based check.)
+    local failed_jobs
+    failed_jobs=$($KUBECTL -n k8s-upgrade get jobs \
+        -o jsonpath='{range .items[*]}{.metadata.name}{"\t"}{.status.conditions[?(@.type=="Failed")].status}{"\n"}{end}' 2>/dev/null \
+        | awk -F'\t' '$2=="True" && $1 ~ /^k8s-upgrade-/{print $1}' | paste -sd' ' - || true)
+
     # Status logic.
     local stalled=0
     if [[ "${in_flight:-0}" == "1" && "$started_int" -gt 0 ]]; then
@@ -463,6 +474,10 @@ collect_k8s() {
         K8S_STATUS_ICON="✗"; K8S_STATUS_TEXT="detection stale"
         K8S_NOTES="last detection >9d ago"
         raise_exit 2
+    elif [[ -n "$failed_jobs" ]]; then
+        K8S_STATUS_ICON="✗"; K8S_STATUS_TEXT="chain failed"
+        K8S_NOTES="failed upgrade Job(s): $failed_jobs — pipeline wedged. Inspect: kubectl -n k8s-upgrade describe job <name> (the retry-on-failure guard re-spawns on the next detection cycle)"
+        raise_exit 2
     elif [[ "${in_flight:-0}" == "1" ]]; then
         K8S_STATUS_ICON="…"; K8S_STATUS_TEXT="in-flight"
         K8S_NOTES="upgrade chain running"
diff --git a/stacks/k8s-version-upgrade/main.tf b/stacks/k8s-version-upgrade/main.tf
index 21d11427..58e5715c 100644
--- a/stacks/k8s-version-upgrade/main.tf
+++ b/stacks/k8s-version-upgrade/main.tf
@@ -451,9 +451,22 @@ resource "kubernetes_cron_job_v1" "k8s_version_check" {
                 #    Idempotency: deterministic name reconciles via `apply`.
                 JOB_NAME="k8s-upgrade-preflight-$${TARGET//./-}"
 
+                # Retry-on-failure idempotency: skip only if an existing preflight
+                # Job is Active/Complete. A *Failed* preflight (aborted on a
+                # transient gate, e.g. a spurious critical alert) is deleted and
+                # re-spawned — otherwise its deterministic name + 7d TTL wedges
+                # the entire pipeline until it ages out. (Stuck-pipeline fix
+                # 2026-06-17: a transient critical alert wedged 1.34.9 for 5 days.)
                 if /usr/local/bin/kubectl -n k8s-upgrade get job "$JOB_NAME" >/dev/null 2>&1; then
-                  slack "Preflight Job $JOB_NAME already exists (rerunning detection mid-flight?)"
-                  exit 0
+                  JOB_FAILED=$(/usr/local/bin/kubectl -n k8s-upgrade get job "$JOB_NAME" \
+                    -o jsonpath='{.status.conditions[?(@.type=="Failed")].status}' 2>/dev/null || true)
+                  if [ "$JOB_FAILED" = "True" ]; then
+                    slack "Preflight Job $JOB_NAME exists but FAILED — deleting and re-spawning"
+                    /usr/local/bin/kubectl -n k8s-upgrade delete job "$JOB_NAME" --wait=true >/dev/null 2>&1 || true
+                  else
+                    slack "Preflight Job $JOB_NAME already exists (active/complete) — skipping"
+                    exit 0
+                  fi
                 fi
 
                 export JOB_NAME PHASE_NEXT=preflight TARGET_NODE_NEXT="" \
diff --git a/stacks/k8s-version-upgrade/scripts/upgrade-step.sh b/stacks/k8s-version-upgrade/scripts/upgrade-step.sh
index b10b395d..f46e1af7 100644
--- a/stacks/k8s-version-upgrade/scripts/upgrade-step.sh
+++ b/stacks/k8s-version-upgrade/scripts/upgrade-step.sh
@@ -222,9 +222,23 @@ spawn_next() {
   local job_name="k8s-upgrade-${NEXT_PHASE}-${TARGET_VERSION//./-}"
   [ -n "${NEXT_TARGET_NODE:-}" ] && job_name="${job_name}-${NEXT_TARGET_NODE}"
 
+  # Retry-on-failure idempotency: skip an existing next-Job ONLY if it is
+  # Active or Complete. A *Failed* Job (a phase that aborted on a transient
+  # gate) is deleted and re-created — otherwise its deterministic name plus
+  # ttlSecondsAfterFinished (7d) would block the whole chain from re-running
+  # that phase until the dead Job aged out. (Stuck-pipeline fix 2026-06-17:
+  # a transient critical alert wedged the 1.34.9 preflight for 5 days.)
   if $KUBECTL -n "$NS" get job "$job_name" >/dev/null 2>&1; then
-    echo "Next Job $job_name already exists; idempotent skip."
-    return 0
+    local job_failed
+    job_failed=$($KUBECTL -n "$NS" get job "$job_name" \
+      -o jsonpath='{.status.conditions[?(@.type=="Failed")].status}' 2>/dev/null || true)
+    if [ "$job_failed" = "True" ]; then
+      echo "Next Job $job_name exists but FAILED — deleting and re-spawning."
+      $KUBECTL -n "$NS" delete job "$job_name" --wait=true >/dev/null 2>&1 || true
+    else
+      echo "Next Job $job_name already exists (active/complete); idempotent skip."
+      return 0
+    fi
   fi
 
   local scheduling_block=""
diff --git a/stacks/monitoring/modules/monitoring/prometheus_chart_values.tpl b/stacks/monitoring/modules/monitoring/prometheus_chart_values.tpl
index 4ca6667c..3895fa04 100755
--- a/stacks/monitoring/modules/monitoring/prometheus_chart_values.tpl
+++ b/stacks/monitoring/modules/monitoring/prometheus_chart_values.tpl
@@ -2224,6 +2224,29 @@ serverFiles:
               severity: critical
             annotations:
               summary: "K8s upgrade has been in flight for >90 min — chain is stuck. Check: kubectl -n k8s-upgrade get jobs"
+          # K8sUpgradeChainJobFailed: catches a FAILED phase Job even when it
+          # aborts BEFORE pushing k8s_upgrade_in_flight=1. The preflight gates
+          # (nodes-ready, halt-on-alert, settle-window, kubeadm-plan) all exit
+          # pre-metric, so a failed preflight is invisible to K8sUpgradeStalled
+          # and EtcdPreUpgradeSnapshotMissing (both need in_flight=1) AND to
+          # upgrade_state.sh — exactly how a transient critical alert wedged the
+          # 1.34.9 preflight for 5 days (2026-06-17). With the retry-on-failure
+          # idempotency guard the next detection cycle deletes + re-spawns it, so
+          # this firing for 15m means it re-failed: investigate the root cause.
+          # NB: keyed on failed-pod count (bare >0, matching the file's other
+          # job-failure alerts) not the terminal Failed *condition* — so a phase
+          # whose 1st pod failed but whose retry succeeded keeps this firing until
+          # the Job's 7d TTL expires. Accepted: warning-only + alert-on-change
+          # (notifies once) + send_resolved, and upgrade_state.sh uses the precise
+          # Failed condition. A false-positive here beats missing a real wedge.
+          - alert: K8sUpgradeChainJobFailed
+            expr: kube_job_status_failed{namespace="k8s-upgrade", job_name=~"k8s-upgrade-.*"} > 0
+            for: 15m
+            labels:
+              severity: warning
+              subsystem: k8s-upgrade
+            annotations:
+              summary: "K8s upgrade chain Job {{ $labels.job_name }} has failed pods — pipeline likely wedged. kubectl -n k8s-upgrade get jobs ; kubectl -n k8s-upgrade describe job {{ $labels.job_name }}"
       - name: "Traefik Ingress"
         rules:
           - alert: TraefikDown
@@ -3076,10 +3099,15 @@ serverFiles:
           - alert: WebterminalTtydUnreachable
             # In-cluster probe to ttyd Service. Bypasses Cloudflare/Traefik/
             # Authentik, so non-200 means ttyd itself is down on the DevVM.
+            # severity=warning (was critical until 2026-06-17): ttyd is a DevVM
+            # developer-convenience web terminal, not cluster infrastructure.
+            # As `critical` it tripped the k8s-upgrade preflight's halt-on-alert
+            # gate and — with the old no-retry idempotency — wedged the 1.34.9
+            # upgrade for 5 days. It is not upgrade-blocking; warning is correct.
             expr: webterminal_probe_ttyd_status{job="webterminal-probe"} != 200 and on() (time() - process_start_time_seconds{job="prometheus"}) > 900
             for: 10m
             labels:
-              severity: critical
+              severity: warning
               subsystem: webterminal
             annotations:
               summary: "ttyd in-cluster probe got HTTP {{ $value }} (expected 200) — ttyd on the DevVM (10.0.10.10:7681) is down. `systemctl status ttyd` on devvm."