diff --git a/vendor/easy-asterisk/docker/entrypoint.sh b/vendor/easy-asterisk/docker/entrypoint.sh
index 943b3d6..7bdf744 100755
--- a/vendor/easy-asterisk/docker/entrypoint.sh
+++ b/vendor/easy-asterisk/docker/entrypoint.sh
@@ -464,7 +464,20 @@ fi
 # ── 11. Signal handling for clean shutdown ────────────────────
 cleanup() {
     log_info "Shutting down..."
-    pkill -f "easy-asterisk-webadmin" 2>/dev/null || true
+    # pkill only sends the signal and returns immediately — it doesn't wait
+    # for the process to actually exit and release its listening socket.
+    # Under network_mode: host there's no Docker-managed port mapping to
+    # tear down, so the next container's bind attempt races however long
+    # this process actually takes to die. Wait for it (briefly) instead of
+    # racing the next container's startup — it retries too now, but a
+    # clean handoff here means it usually shouldn't need to.
+    if pkill -f "easy-asterisk-webadmin" 2>/dev/null; then
+        for i in $(seq 1 20); do
+            pgrep -f "easy-asterisk-webadmin" >/dev/null 2>&1 || break
+            sleep 0.1
+        done
+        pkill -9 -f "easy-asterisk-webadmin" 2>/dev/null || true
+    fi
     asterisk -rx "core stop now" 2>/dev/null || true
     exit 0
 }
diff --git a/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh b/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
index a3b1c55..d16fa12 100755
--- a/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
+++ b/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
@@ -4116,6 +4116,7 @@ import json
 import subprocess
 import os
 import re
+import time
 import base64
 import hashlib
 import html
@@ -6134,7 +6135,25 @@ class WebAdminHandler(http.server.BaseHTTPRequestHandler):
         self.wfile.write(json.dumps(data).encode())
 
 def main():
-    with socketserver.TCPServer(("", PORT), WebAdminHandler) as httpd:
+    # A container recreate under network_mode: host depends on the *previous*
+    # container's web admin process actually dying before the port is free —
+    # there's no Docker-managed port mapping to instantly release it like
+    # there would be in bridge mode. A fast recreate-right-after-recreate can
+    # briefly race that teardown. Retry instead of crashing on the first
+    # failure, which otherwise means the web admin silently never comes up.
+    httpd = None
+    last_err = None
+    for attempt in range(10):
+        try:
+            httpd = socketserver.TCPServer(("", PORT), WebAdminHandler)
+            break
+        except OSError as e:
+            last_err = e
+            print(f"Port {PORT} not free yet ({e}), retrying...")
+            time.sleep(2)
+    if httpd is None:
+        raise last_err
+    with httpd:
         print(f"Easy Asterisk Web Admin running on port {PORT}")
         httpd.serve_forever()