diff --git a/vendor/easy-asterisk/docker/entrypoint.sh b/vendor/easy-asterisk/docker/entrypoint.sh
index 1cadc6d..943b3d6 100755
--- a/vendor/easy-asterisk/docker/entrypoint.sh
+++ b/vendor/easy-asterisk/docker/entrypoint.sh
@@ -431,8 +431,15 @@ fi
 chown -R asterisk:asterisk /etc/asterisk /var/lib/asterisk /var/log/asterisk /var/spool/asterisk /var/run/asterisk 2>/dev/null || true
 
 # ── 10. Start Web Admin in background ─────────────────────────
-# The web admin script is generated by the 'easy-asterisk' management tool.
-# On first run: docker exec -it easy-asterisk easy-asterisk → Web Admin menu → Start
+# The web admin script is generated by the 'easy-asterisk' management tool,
+# but it only lives in the container's writable layer (not baked into the
+# image or bind-mounted), so it's gone every time the container is
+# recreated. Regenerate it unconditionally instead of only starting it if
+# it happens to already exist — otherwise the web admin never comes back
+# on its own after a restart, requiring a manual CLI trip every time.
+if [[ -x /usr/local/bin/easy-asterisk ]]; then
+    /usr/local/bin/easy-asterisk --write-web-admin-script >/dev/null 2>&1 || true
+fi
 if [[ -f "$WEB_ADMIN_SCRIPT" ]]; then
     log_info "Starting Web Admin on port ${WEB_ADMIN_PORT:-8080}..."
     WEBADMIN_PORT="${WEB_ADMIN_PORT:-8080}" \
diff --git a/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh b/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
index 3cd0981..4aad948 100755
--- a/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
+++ b/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
@@ -7024,4 +7024,16 @@ if [[ "${1:-}" == "--rebuild-dialplan" ]]; then
     exit 0
 fi
 
+# Non-interactive entry point used by the container entrypoint on every
+# start. create_web_admin_script() writes /usr/local/bin/easy-asterisk-
+# webadmin, but that file lives only in the container's writable layer —
+# it isn't baked into the image or bind-mounted anywhere — so it's wiped
+# on every recreate. Without regenerating it here, the web admin only
+# ever starts after someone manually runs it once from the interactive
+# CLI menu, which defeats the point of it auto-starting at all.
+if [[ "${1:-}" == "--write-web-admin-script" ]]; then
+    create_web_admin_script
+    exit 0
+fi
+
 main "$@"