diff --git a/vendor/easy-asterisk/docker/entrypoint.sh b/vendor/easy-asterisk/docker/entrypoint.sh
index b62caa9..1181c3e 100755
--- a/vendor/easy-asterisk/docker/entrypoint.sh
+++ b/vendor/easy-asterisk/docker/entrypoint.sh
@@ -479,15 +479,19 @@ for i in $(seq 1 60); do
     sleep 1
 done
 
-# Verify PJSIP transports are listening
+# Verify PJSIP transports are listening. res_pjsip finishes binding its
+# transports a beat after "core show version" first responds, so a single
+# immediate check can catch it mid-startup and misreport TLS as down even
+# though it comes up a second later — poll for a few seconds before giving up.
 tls_ok=false
 udp_ok=false
-if asterisk -rx "pjsip show transports" 2>/dev/null | grep -q "transport-tls"; then
-    tls_ok=true
-fi
-if asterisk -rx "pjsip show transports" 2>/dev/null | grep -q "transport-udp"; then
-    udp_ok=true
-fi
+for i in $(seq 1 10); do
+    transports_output=$(asterisk -rx "pjsip show transports" 2>/dev/null)
+    echo "$transports_output" | grep -q "transport-tls" && tls_ok=true
+    echo "$transports_output" | grep -q "transport-udp" && udp_ok=true
+    $tls_ok && $udp_ok && break
+    sleep 1
+done
 
 # Check if port 5061 is actually bound
 tls_listen=""
diff --git a/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh b/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
index bc63904..958c8ce 100755
--- a/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
+++ b/vendor/easy-asterisk/easy-asterisk-v0.10.0.sh
@@ -4340,6 +4340,7 @@ def delete_device(extension):
         with open(PJSIP_CONF, 'w') as f:
             f.writelines(new_lines)
         subprocess.run(['asterisk', '-rx', 'pjsip reload'], capture_output=True)
+        subprocess.run(['/usr/local/bin/easy-asterisk', '--rebuild-dialplan'], capture_output=True)
         return True, "Device deleted"
     return False, "Device not found"
 
@@ -4413,6 +4414,7 @@ def rename_device(extension, new_name):
         with open(PJSIP_CONF, 'w') as f:
             f.writelines(new_lines)
         subprocess.run(['asterisk', '-rx', 'pjsip reload'], capture_output=True)
+        subprocess.run(['/usr/local/bin/easy-asterisk', '--rebuild-dialplan'], capture_output=True)
         return True, "Device renamed"
     return False, "Device not found"
 
@@ -4525,6 +4527,7 @@ def change_device_category(extension, new_category):
         with open(PJSIP_CONF, 'w') as f:
             f.writelines(new_lines)
         subprocess.run(['asterisk', '-rx', 'pjsip reload'], capture_output=True)
+        subprocess.run(['/usr/local/bin/easy-asterisk', '--rebuild-dialplan'], capture_output=True)
         return True, "Category changed"
     return False, "Device not found"
 
@@ -4774,6 +4777,7 @@ qualify_frequency=30
 
     subprocess.run(['asterisk', '-rx', 'pjsip reload'], capture_output=True)
     subprocess.run(['chown', 'asterisk:asterisk', PJSIP_CONF], capture_output=True)
+    subprocess.run(['/usr/local/bin/easy-asterisk', '--rebuild-dialplan'], capture_output=True)
 
     return True, {'extension': extension, 'password': password, 'name': name}
 
@@ -6926,4 +6930,14 @@ main() {
     show_main_menu
 }
 
+# Non-interactive entry point used by the web admin (Python) after any
+# device/room change — regenerates extensions.conf's [intercom] context
+# and reloads it. Without this, PJSIP endpoints register fine but calls
+# between them fail with "extension not found" since nothing else ever
+# rebuilds the dialplan after the initial container boot.
+if [[ "${1:-}" == "--rebuild-dialplan" ]]; then
+    rebuild_dialplan quiet
+    exit 0
+fi
+
 main "$@"