diff --git a/pi/skills/control-agent/startup-cleanup.sh b/pi/skills/control-agent/startup-cleanup.sh
index 98bd5a2..e6383e2 100755
--- a/pi/skills/control-agent/startup-cleanup.sh
+++ b/pi/skills/control-agent/startup-cleanup.sh
@@ -87,17 +87,35 @@ mkdir -p "$BRIDGE_LOG_DIR"
 # --- Kill anything holding port 7890, any existing bridge tmux session,
 #     and any leftover old-style PID-file supervisor.
 echo "Cleaning up old bridge..."
+
+# Kill the tmux session first — this stops the restart loop from respawning
+# the bridge while we're trying to clean up the port.
+tmux kill-session -t "$BRIDGE_TMUX_SESSION" 2>/dev/null || true
+
+# Now gracefully stop any process on the port. SIGTERM lets the bridge close
+# the HTTP server and release the port cleanly; SIGKILL is the fallback.
 PORT_PIDS=$(lsof -ti :7890 2>/dev/null || true)
 if [ -n "$PORT_PIDS" ]; then
-  echo "Killing processes on port 7890: $PORT_PIDS"
-  echo "$PORT_PIDS" | xargs kill -9 2>/dev/null || true
-  sleep 1
+  echo "Stopping processes on port 7890 (SIGTERM): $PORT_PIDS"
+  echo "$PORT_PIDS" | xargs kill 2>/dev/null || true
+  # Wait up to 3s for graceful shutdown
+  for i in 1 2 3; do
+    sleep 1
+    PORT_PIDS=$(lsof -ti :7890 2>/dev/null || true)
+    [ -z "$PORT_PIDS" ] && break
+  done
+  # Force-kill anything that didn't exit
+  if [ -n "$PORT_PIDS" ]; then
+    echo "Force-killing stubborn processes: $PORT_PIDS"
+    echo "$PORT_PIDS" | xargs kill -9 2>/dev/null || true
+    sleep 1
+  fi
 fi
-tmux kill-session -t "$BRIDGE_TMUX_SESSION" 2>/dev/null || true
+
 OLD_PID_FILE="$HOME/.pi/agent/slack-bridge.pid"
 if [ -f "$OLD_PID_FILE" ]; then
   OLD_PID="$(cat "$OLD_PID_FILE" 2>/dev/null || true)"
-  [ -n "$OLD_PID" ] && kill -9 "$OLD_PID" 2>/dev/null || true
+  [ -n "$OLD_PID" ] && kill "$OLD_PID" 2>/dev/null || true
   rm -f "$OLD_PID_FILE"
 fi
 
@@ -151,6 +169,12 @@ tmux new-session -d -s "$BRIDGE_TMUX_SESSION" "\
     exit_code=\$?; \
     echo \"[\$(date -Is)] bridge: exited with code \$exit_code, restarting in 5s\" >> $BRIDGE_LOG_FILE; \
     sleep 5; \
+    tries=0; \
+    while lsof -ti :7890 >/dev/null 2>&1 && [ \$tries -lt 10 ]; do \
+      echo \"[\$(date -Is)] bridge: port 7890 still in use, waiting...\" >> $BRIDGE_LOG_FILE; \
+      sleep 2; \
+      tries=\$((tries + 1)); \
+    done; \
   done"
 
 echo "Bridge tmux session: $BRIDGE_TMUX_SESSION"
diff --git a/slack-bridge/broker-bridge.mjs b/slack-bridge/broker-bridge.mjs
index 9bc00a6..2b42e38 100755
--- a/slack-bridge/broker-bridge.mjs
+++ b/slack-bridge/broker-bridge.mjs
@@ -885,6 +885,36 @@ function getLogLinesForResponse(url) {
   return lines;
 }
 
+/** Reference to the HTTP server so we can close it on shutdown. */
+let apiServer = null;
+let shuttingDown = false;
+
+/**
+ * Graceful shutdown: close the HTTP server (releases the port), then exit.
+ * Called on SIGTERM/SIGINT so restarts don't fight over the port.
+ */
+function gracefulShutdown(signal) {
+  if (shuttingDown) return;
+  shuttingDown = true;
+  logInfo(`🛑 received ${signal} — shutting down gracefully`);
+  if (apiServer) {
+    apiServer.close(() => {
+      logInfo("🛑 HTTP server closed, exiting");
+      process.exit(0);
+    });
+    // Force exit after 5s if connections don't drain
+    setTimeout(() => {
+      logWarn("🛑 forceful exit after 5s timeout");
+      process.exit(1);
+    }, 5000).unref();
+  } else {
+    process.exit(0);
+  }
+}
+
+process.on("SIGTERM", () => gracefulShutdown("SIGTERM"));
+process.on("SIGINT", () => gracefulShutdown("SIGINT"));
+
 function startApiServer() {
   const server = createServer(async (req, res) => {
     const url = new URL(req.url, `http://localhost:${API_PORT}`);
@@ -1024,9 +1054,33 @@ function startApiServer() {
     }
   });
 
-  server.listen(API_PORT, "127.0.0.1", () => {
+  // Retry with backoff if the port is still held by a dying predecessor.
+  const MAX_BIND_RETRIES = 5;
+  const BIND_RETRY_DELAY_MS = 2000;
+  let bindAttempt = 0;
+
+  function tryListen() {
+    bindAttempt++;
+    server.listen(API_PORT, "127.0.0.1");
+  }
+
+  server.on("listening", () => {
+    apiServer = server;
     logInfo(`📡 Outbound API listening on http://127.0.0.1:${API_PORT}`);
   });
+
+  server.on("error", (err) => {
+    if (err.code === "EADDRINUSE" && bindAttempt < MAX_BIND_RETRIES) {
+      logWarn(`⚠️ port ${API_PORT} in use, retrying in ${BIND_RETRY_DELAY_MS}ms (attempt ${bindAttempt}/${MAX_BIND_RETRIES})`);
+      server.close();
+      setTimeout(tryListen, BIND_RETRY_DELAY_MS);
+    } else {
+      logError(`❌ HTTP server error: ${err.message}`);
+      process.exit(1);
+    }
+  });
+
+  tryListen();
 }
 
 async function startPollLoop() {