diff --git a/Dockerfile-alpine.template b/Dockerfile-alpine.template
index 8c464dfd4..09ba3a393 100644
--- a/Dockerfile-alpine.template
+++ b/Dockerfile-alpine.template
@@ -76,3 +76,5 @@ RUN set -x \
     && if [ -n "/etc/apk/keys/nginx_signing.rsa.pub" ]; then rm -f /etc/apk/keys/nginx_signing.rsa.pub; fi \
 # Bring in curl and ca-certificates to make registering on DNS SD easier
     && apk add --no-cache curl ca-certificates
+# Add support for manually monitoring files to trigger server reloads
+    && apk add --no-cache inotify-tools
diff --git a/entrypoint/99-monitor-config-changes.sh b/entrypoint/99-monitor-config-changes.sh
new file mode 100755
index 000000000..c2ed02b3d
--- /dev/null
+++ b/entrypoint/99-monitor-config-changes.sh
@@ -0,0 +1,44 @@
+#!/bin/sh
+# vim:sw=2:ts=2:sts=2:et
+
+set -eu
+if [ -n "${DEBUG_TRACE_SH:-}" ] && \
+   [ "${DEBUG_TRACE_SH:-}" != "${DEBUG_TRACE_SH#*"$(basename "${0}")"*}" ] || \
+   [ "${DEBUG_TRACE_SH:-}" = 'all' ]; then
+  set -x
+fi
+
+LC_ALL=C
+
+if [ -e "${NGINX_ENTRYPOINT_MONITOR_PID:=/run/nginx_monitor.pid}" ] ||
+   [ -z "${NGINX_ENTRYPOINT_MONITOR_CONFIG+monitor}" ] || \
+   ! command -v inotifywait; then
+  exit 0
+fi
+
+echo "Monitoring for changes in '${NGINX_ENTRYPOINT_MONITOR_CONFIG:=/etc/nginx}'"
+while true; do
+  inotifywait \
+    --recursive \
+    --event 'create' \
+    --event 'delete' \
+    --event 'modify' \
+    --event 'move' \
+    "${NGINX_ENTRYPOINT_MONITOR_CONFIG}"
+
+  sleep "${NGINX_ENTRYPOINT_MONITOR_DELAY:-10s}"
+
+  if [ ! -e "${NGINX_ENTRYPOINT_MONITOR_PID}" ]; then
+    logger -s -t 'nginx' -p 'local0.3' 'Monitor failure or exit requested'
+    break
+  fi
+
+  if nginx -t; then
+    nginx -s
+  else
+    logger -s -t 'nginx' -p 'local0.3' 'Refusing to reload config, config error'
+  fi
+done &
+echo "${!}" > "${NGINX_ENTRYPOINT_MONITOR_PID}"
+
+exit 0