diff --git a/bot/vikingbot/__init__.py b/bot/vikingbot/__init__.py
index ce093e3dd..a9a34240e 100644
--- a/bot/vikingbot/__init__.py
+++ b/bot/vikingbot/__init__.py
@@ -3,8 +3,13 @@
 """
 
 import warnings
+from importlib.metadata import PackageNotFoundError, version as _pkg_version
+
+try:
+    __version__ = _pkg_version("openviking")
+except PackageNotFoundError:
+    __version__ = "0.0.0+unknown"
 
-__version__ = "0.1.3"
 __logo__ = "🐈"
 
 # Suppress RequestsDependencyWarning from requests module
diff --git a/bot/vikingbot/cli/commands.py b/bot/vikingbot/cli/commands.py
index 907f3263e..431e62361 100644
--- a/bot/vikingbot/cli/commands.py
+++ b/bot/vikingbot/cli/commands.py
@@ -4,6 +4,7 @@
 import json
 import os
 import select
+import socket
 import sys
 import time
 import warnings
@@ -83,6 +84,32 @@ def _init_bot_data(config):
     set_bot_data_path(config.bot_data_path)
 
 
+def _abort_if_port_in_use(port: int, label: str) -> None:
+    """Exit with a clear message if anything is already listening on ``port``.
+
+    Without this check, a stale process holding the port keeps serving
+    traffic while a freshly-started gateway silently fails to bind — the
+    operator believes they upgraded but the old (potentially unpatched)
+    binary is still answering requests.
+    """
+    with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
+        s.settimeout(0.5)
+        try:
+            s.connect(("127.0.0.1", port))
+            in_use = True
+        except (ConnectionRefusedError, socket.timeout, OSError):
+            in_use = False
+    if in_use:
+        print(
+            f"Error: {label} port {port} is already in use.\n"
+            f"  A previous process is still bound — refusing to start a duplicate.\n"
+            f"  Identify it:  lsof -nP -iTCP:{port} -sTCP:LISTEN\n"
+            f"  Kill it, then retry.",
+            file=sys.stderr,
+        )
+        sys.exit(1)
+
+
 # ---------------------------------------------------------------------------
 # CLI input: prompt_toolkit for editing, paste, history, and display
 # ---------------------------------------------------------------------------
@@ -249,6 +276,8 @@ def gateway(
 ):
     """Start the vikingbot gateway with OpenAPI chat enabled by default."""
 
+    _abort_if_port_in_use(port, "vikingbot gateway")
+
     if verbose:
         import logging
 
diff --git a/openviking/server/bootstrap.py b/openviking/server/bootstrap.py
index c773fc630..0eda1ee61 100644
--- a/openviking/server/bootstrap.py
+++ b/openviking/server/bootstrap.py
@@ -5,6 +5,7 @@
 import argparse
 import os
 import shutil
+import socket
 import subprocess
 import sys
 import time
@@ -34,6 +35,34 @@ def _get_version() -> str:
         return "unknown"
 
 
+VIKINGBOT_DEFAULT_PORT = 18790
+
+
+def _abort_if_port_in_use(port: int, label: str) -> None:
+    """Exit with a clear message if anything is already listening on ``port``.
+
+    Without this, ``--with-bot`` would spawn a vikingbot subprocess that
+    silently fails to bind while a stale process keeps serving traffic —
+    the operator believes they upgraded but the old binary still answers.
+    """
+    with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
+        s.settimeout(0.5)
+        try:
+            s.connect(("127.0.0.1", port))
+            in_use = True
+        except (ConnectionRefusedError, socket.timeout, OSError):
+            in_use = False
+    if in_use:
+        print(
+            f"Error: {label} port {port} is already in use.\n"
+            f"  A previous process is still bound — refusing to start a duplicate.\n"
+            f"  Identify it:  lsof -nP -iTCP:{port} -sTCP:LISTEN\n"
+            f"  Kill it, then retry.",
+            file=sys.stderr,
+        )
+        sys.exit(1)
+
+
 def _normalize_host_arg(host: Optional[str]) -> Optional[str]:
     """Normalize special CLI host values."""
     if host is None:
@@ -170,6 +199,7 @@ def main():
 
     bot_process: Optional[BotProcess] = None
     if config.with_bot:
+        _abort_if_port_in_use(VIKINGBOT_DEFAULT_PORT, "vikingbot gateway")
         print(f"Bot API proxy enabled, forwarding to {config.bot_api_url}")
         # Determine if bot logging should be enabled
         enable_bot_logging = args.enable_bot_logging