diff --git a/ansible/roles/ups/defaults/main.yml b/ansible/roles/ups/defaults/main.yml
index b8d8408..757b3d2 100644
--- a/ansible/roles/ups/defaults/main.yml
+++ b/ansible/roles/ups/defaults/main.yml
@@ -34,3 +34,8 @@ ups_deps:
 
 # Secrets live in ansible/vars/vault.yml (no vault_ prefix, per repo
 # convention): nut_upsmon_password, nut_truenas_password, idrac_password
+
+# Seconds between upsd restart attempts. Paired with StartLimitIntervalSec=0 in
+# the nut-server drop-in, so a late network address retries patiently instead of
+# exhausting the default five-tries-per-interval and giving up for good.
+ups_server_restart_sec: 10
diff --git a/ansible/roles/ups/handlers/main.yml b/ansible/roles/ups/handlers/main.yml
index e2af69c..d07685e 100644
--- a/ansible/roles/ups/handlers/main.yml
+++ b/ansible/roles/ups/handlers/main.yml
@@ -16,11 +16,16 @@
     name: "nut-driver@{{ ups_name }}.service"
     state: restarted
 
+# daemon_reload so the drop-in under nut-server.service.d is picked up. The
+# reload also clears the start-limit counter, which matters because a unit that
+# has latched into "start request repeated too quickly" refuses a plain restart
+# until that state is reset.
 - name: restart nut server
   become: true
   ansible.builtin.systemd:
     name: nut-server.service
     state: restarted
+    daemon_reload: true
 
 - name: restart nut monitor
   become: true
diff --git a/ansible/roles/ups/tasks/nut.yml b/ansible/roles/ups/tasks/nut.yml
index 3f86819..ef6cbe4 100644
--- a/ansible/roles/ups/tasks/nut.yml
+++ b/ansible/roles/ups/tasks/nut.yml
@@ -42,6 +42,29 @@
   notify: restart nut server
   tags: ups
 
+# upsd binds an explicit address, so it must not start before that address
+# exists. See the template for the boot race this fixes.
+- name: ensure nut-server drop-in directory exists
+  become: true
+  ansible.builtin.file:
+    path: /etc/systemd/system/nut-server.service.d
+    state: directory
+    owner: root
+    group: root
+    mode: '0755'
+  tags: ups
+
+- name: order upsd after the network is actually online
+  become: true
+  ansible.builtin.template:
+    src: nut-server-network-online.conf.j2
+    dest: /etc/systemd/system/nut-server.service.d/10-network-online.conf
+    owner: root
+    group: root
+    mode: '0644'
+  notify: restart nut server
+  tags: ups
+
 - name: deploy upsd users
   become: true
   ansible.builtin.template:
diff --git a/ansible/roles/ups/templates/nut-server-network-online.conf.j2 b/ansible/roles/ups/templates/nut-server-network-online.conf.j2
new file mode 100644
index 0000000..01555d6
--- /dev/null
+++ b/ansible/roles/ups/templates/nut-server-network-online.conf.j2
@@ -0,0 +1,30 @@
+# {{ ansible_managed }}
+# upsd binds explicit addresses (see upsd.conf), but the packaged unit only
+# orders itself After=network.target -- which is satisfied when networking
+# STARTS, not when an address actually exists. The shipped unit even carries
+# these two lines commented out, because upstream knows the case.
+#
+# On 2026-08-28 the host came up and upsd tried to bind 11 seconds into boot,
+# before NetworkManager had assigned the address:
+#   upsd: not listening on {{ ups_listen_addr }} port {{ ups_listen_port }}
+#   upsd: Fatal error: some listening interfaces were not available
+# It then burned all five of the default restart attempts inside one second,
+# tripped the start limit, and stayed dead. truenas monitors this host as a
+# SLAVE (MONITOR cyberpower@{{ ups_listen_addr }}:{{ ups_listen_port }}), so
+# it alarmed NOCOMM continuously until someone noticed. The UPS driver itself
+# was fine throughout -- only the server that publishes its state was gone.
+#
+# NetworkManager-wait-online is enabled on this host, so network-online.target
+# genuinely waits for addresses rather than just for the service to start.
+#
+# The restart settings are belt and braces: StartLimitIntervalSec=0 removes the
+# rate limit so a slow address can never exhaust the attempts, and RestartSec
+# spaces the retries out instead of hammering five times in a second.
+[Unit]
+Wants=network-online.target
+After=network-online.target
+StartLimitIntervalSec=0
+
+[Service]
+Restart=on-failure
+RestartSec={{ ups_server_restart_sec }}