diff --git a/services/headscale-ddns/README.md b/services/headscale-ddns/README.md
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+# headscale-ddns — keep `headscale.phasefinal.com` pointed at the NH3 WAN v4
+
+A user timer on nh3-dev, every 10 minutes: read the WAN v4, PATCH the Cloudflare
+A record if it moved. It is how every mesh client finds the control plane, so a
+silent failure here eventually costs the mesh.
+
+Installed at `~/.local/bin/headscale-ddns.sh` with user units
+`headscale-ddns.{service,timer}`. **Tracked here since 2026-09-22** — it was
+running untracked before that, so a fix to it lived on exactly one disk.
+
+## The 2026-09-22 failure, and what it exposed
+
+The unit failed at 15:28 (exit 1) after succeeding all afternoon. Cause was
+transient — `icanhazip.com` did not answer inside its 10s cap, so `$IP` came back
+empty and the regex guard refused it. No DNS impact: the record already held the
+right address and the next timer run succeeded.
+
+**What actually mattered was that the alarm carried no cause.** Both failure
+paths were `|| exit 1` in silence, so the failed-START notifier fired correctly
+and said only "exit status 1". An alarm you cannot act on costs the same triage
+as no alarm.
+
+Two fixes, both verified by making them fail:
+
+- **Every exit path now says why** — a missing vault key names the key; an empty
+  token is distinguished from a failed read; a dead WAN lookup says so and adds
+  *"DNS left unchanged"*, which is the fact the reader needs.
+- **The WAN lookup retries 3×** with announced attempts. One third-party blip
+  should not page a human, and a *silent* retry would hide a degrading
+  dependency.
+
+## ⚠ The vault read is 17 of the script's 18 seconds
+
+Measured 2026-09-22: `secret get` takes **~17s**, everything else ~1s. It runs
+every 10 minutes. That is not a fault — but it bounds any retry budget here, and
+it is a fleet-wide cost worth knowing: svos-dev's own alarm unit carries the same
+17-second note. Any script in a timer that reads the vault pays it.
+
+## Triage
+
+```sh
+systemctl --user status headscale-ddns.service
+journalctl --user -u headscale-ddns.service -n 50 --no-pager
+dig +short headscale.phasefinal.com @1.1.1.1     # the thing that actually matters
+/home/lkraven/.local/bin/headscale-ddns.sh       # safe to run by hand; idempotent
+```
+
+A failed unit clears itself on the next timer run; it does not need
+`reset-failed` unless you want the state gone immediately.
diff --git a/services/headscale-ddns/headscale-ddns.service b/services/headscale-ddns/headscale-ddns.service
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+++ b/services/headscale-ddns/headscale-ddns.service
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+[Unit]
+Description=Update headscale.phasefinal.com A record to NH3 WAN v4
+[Service]
+Type=oneshot
+ExecStart=/home/lkraven/.local/bin/headscale-ddns.sh
+
+# /home/lkraven/.config/systemd/user/headscale-ddns.service.d/10-onfailure-althing.conf
+# Installed as <unit>.service.d/10-onfailure-althing.conf on every fleet user
+# unit. A drop-in rather than an edit to the unit file so it is visible in
+# `systemctl --user cat`, reversible by deleting one file, and survives the
+# unit being reinstalled by its own deploy.
+#
+# %n is the failing unit's full name; the template receives it as %I.
+[Unit]
+OnFailure=althing-notify-failure@%n.service
diff --git a/services/headscale-ddns/headscale-ddns.sh b/services/headscale-ddns/headscale-ddns.sh
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+++ b/services/headscale-ddns/headscale-ddns.sh
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+#!/bin/bash
+# Keep headscale.phasefinal.com's A record on NH3's current WAN v4. Token from the vault at run time.
+set -u
+SECRET=/home/lkraven/development/eshpfi-management/services/secrets-broker/secret
+# ⚠ SAY WHY. Both failure paths below used to `|| exit 1` in silence, and on
+# 2026-09-22 15:28 this unit failed for real: the failed-START alarm fired
+# correctly and carried NO CAUSE, because the script had printed nothing. An
+# alarm you cannot act on costs the same triage as no alarm at all.
+T=$($SECRET get nh3-dev/.config/cloudflare/infra-ops-dns-token 2>/dev/null) || {
+  echo "FATAL: vault read failed for nh3-dev/.config/cloudflare/infra-ops-dns-token" >&2; exit 1; }
+[ -n "$T" ] || { echo "FATAL: vault returned an EMPTY token (read succeeded, value blank)" >&2; exit 1; }
+# The WAN lookup leans on a third party, so one blip should not page a human.
+# Measured 2026-09-22: the whole script takes ~18s of which ~17s is the vault
+# read, so three tries at a 10s cap is bounded and still well inside the 10-min
+# timer. Retries are announced -- a silent retry hides a degrading dependency.
+IP=""
+for try in 1 2 3; do
+  IP=$(curl -s -m 10 -4 https://icanhazip.com | tr -d '[:space:]')
+  [[ "$IP" =~ ^[0-9.]+$ ]] && break
+  echo "WARN: WAN lookup attempt $try/3 returned [$IP]" >&2
+  sleep 2
+done
+[[ "$IP" =~ ^[0-9.]+$ ]] || {
+  echo "FATAL: could not determine WAN v4 after 3 attempts (icanhazip.com unreachable or returning junk); DNS left unchanged" >&2; exit 1; }
+ZID=$(curl -s -m 15 -H "Authorization: Bearer $T" "https://api.cloudflare.com/client/v4/zones?name=phasefinal.com" | python3 -c 'import sys,json; print(json.load(sys.stdin)["result"][0]["id"])')
+read -r RID CUR < <(curl -s -m 15 -H "Authorization: Bearer $T" "https://api.cloudflare.com/client/v4/zones/$ZID/dns_records?type=A&name=headscale.phasefinal.com" | python3 -c 'import sys,json; r=json.load(sys.stdin)["result"][0]; print(r["id"], r["content"])')
+[ "$CUR" = "$IP" ] && { echo "unchanged $IP"; exit 0; }
+curl -s -m 15 -X PATCH -H "Authorization: Bearer $T" -H "Content-Type: application/json" "https://api.cloudflare.com/client/v4/zones/$ZID/dns_records/$RID" -d "{\"content\":\"$IP\"}" | python3 -c 'import sys,json; d=json.load(sys.stdin); print("updated", d["success"], d["result"]["content"])'
diff --git a/services/headscale-ddns/headscale-ddns.timer b/services/headscale-ddns/headscale-ddns.timer
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+++ b/services/headscale-ddns/headscale-ddns.timer
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+[Unit]
+Description=headscale DDNS every 10 minutes
+[Timer]
+OnBootSec=2min
+OnUnitActiveSec=10min
+[Install]
+WantedBy=timers.target