diff --git a/nginx/nginx.sh b/nginx/nginx.sh
index d3d4422..9b93d6d 100644
--- a/nginx/nginx.sh
+++ b/nginx/nginx.sh
@@ -1,12 +1,55 @@
 #!/bin/sh
+# Watch /root for cert/config changes and (re)load nginx accordingly.
+#
+# The previous version "reloaded" by running bare `nginx`, which starts a
+# SECOND master that cannot bind 0.0.0.0:443 ("Address in use") and exits, so
+# after the first start NO change ever took effect: cert rotations were silently
+# dropped until a full container restart. SIGHUP (`nginx -s reload`) keeps the
+# listening sockets and re-execs workers with the new config.
+#
+# We also exclude *.crl: the manager's CRL is copied into /root for historical
+# reasons but this nginx never references it (no ssl_crl here), so reacting to
+# it just churned a reload every sync interval (incident 2026-06-13).
+#
+# We watch in --monitor mode so NO event is ever lost. The manager installs the
+# cert as separate Docker writes (pem.crt, then cert.key, then ca.pem); a
+# one-shot inotifywait exits after the first event and stops watching while
+# `nginx -t` runs, so a key write landing in that window is missed and nginx
+# never (re)loads until some unrelated later change. In monitor mode the kernel
+# queues events while we process, so the iteration where both cert and key are
+# present always converges. The outer loop respawns the watch if it ever dies.
+
+start_or_reload() {
+    # `nginx -t` fails when the cert material is not present yet (a fresh
+    # container has an empty /root until the manager installs the cert), which
+    # is expected. Distinguish that from a genuinely broken config so a real
+    # error is not swallowed silently.
+    if ! nginx -t >/dev/null 2>&1; then
+        if [ -s /root/pem.crt ]; then
+            echo "nginx -t failed with cert present (bad config?), not (re)loading:"
+            nginx -t
+        fi
+        return 0
+    fi
+    if pidof nginx >/dev/null 2>&1; then
+        echo "Reloading Nginx Configuration"
+        nginx -s reload
+    else
+        echo "Starting Nginx"
+        nginx
+    fi
+}
+
+# Bring nginx up if usable config + certs are already in place (e.g. a container
+# restart with the certs still on disk); otherwise the first event starts it.
+start_or_reload
+
 while true; do
-  inotifywait --exclude .crt -e create -e modify -e delete -e move /root/
-  # Check NGINX Configuration Test
-  # Only Reload NGINX If NGINX Configuration Test Pass
-  nginx -t
-  if [ $? -eq 0 ]
-  then
-    echo "Reloading Nginx Configuration"
-    nginx
-  fi
-done
\ No newline at end of file
+    inotifywait -m -q --exclude '\.crl$' -e create -e modify -e delete -e move /root/ |
+    while read -r _; do
+        start_or_reload
+    done
+    # inotifywait exited (watch lost / error); back off so we can't busy-spin,
+    # then respawn the monitor.
+    sleep 5
+done