diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8bc0047ae..e08ecccc7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -20,6 +20,7 @@
 
 ### Fixes
 - CLI/Daemon: add `clawdbot logs` tailing and improve restart/service hints across platforms.
+- Gateway/CLI: tighten LAN bind auth checks, warn on mis-keyed gateway tokens, and surface last gateway error when daemon looks running but the port is closed.
 - Auto-reply: keep typing indicators alive during tool execution without changing typing-mode semantics. Thanks @thesash for PR #452.
 - macOS: harden Voice Wake tester/runtime (pause trigger, mic persistence, local-only tester) and keep transcript logs private. Thanks @xadenryan for PR #438.
 - macOS: preserve node bridge tunnel port override so remote nodes connect on the bridge port. Thanks @sircrumpet for PR #364.
diff --git a/docs/gateway/configuration.md b/docs/gateway/configuration.md
index 3527399f6..b0741e479 100644
--- a/docs/gateway/configuration.md
+++ b/docs/gateway/configuration.md
@@ -1555,6 +1555,8 @@ Notes:
 - `clawdbot gateway` refuses to start unless `gateway.mode` is set to `local` (or you pass the override flag).
 - `gateway.port` controls the single multiplexed port used for WebSocket + HTTP (control UI, hooks, A2UI).
 - Precedence: `--port` > `CLAWDBOT_GATEWAY_PORT` > `gateway.port` > default `18789`.
+- Non-loopback binds (`lan`/`tailnet`/`auto`) require auth. Use `gateway.auth.token` (or `CLAWDBOT_GATEWAY_TOKEN`).
+- `gateway.remote.token` is **only** for remote CLI calls; it does not enable local gateway auth. `gateway.token` is ignored.
 
 Auth and Tailscale:
 - `gateway.auth.mode` sets the handshake requirements (`token` or `password`).
diff --git a/docs/gateway/troubleshooting.md b/docs/gateway/troubleshooting.md
index 5f8960238..e812034e9 100644
--- a/docs/gateway/troubleshooting.md
+++ b/docs/gateway/troubleshooting.md
@@ -29,6 +29,18 @@ Doctor/daemon will show runtime state (PID/last exit) and log hints.
 - Linux systemd (if installed): `journalctl --user -u clawdbot-gateway.service -n 200 --no-pager`
 - Windows: `schtasks /Query /TN "Clawdbot Gateway" /V /FO LIST`
 
+### Service Running but Port Not Listening
+
+If the service reports **running** but nothing is listening on the gateway port,
+the Gateway likely refused to bind.
+
+**Check:**
+- `gateway.mode` must be `local` for `clawdbot gateway` and the daemon.
+- Non-loopback binds (`lan`/`tailnet`/`auto`) require auth:
+  `gateway.auth.token` (or `CLAWDBOT_GATEWAY_TOKEN`).
+- `gateway.remote.token` is for remote CLI calls only; it does **not** enable local auth.
+- `gateway.token` is ignored; use `gateway.auth.token`.
+
 ### Address Already in Use (Port 18789)
 
 This means something is already listening on the gateway port.
diff --git a/docs/platforms/exe-dev.md b/docs/platforms/exe-dev.md
index 0261be2fb..b2ccae4a9 100644
--- a/docs/platforms/exe-dev.md
+++ b/docs/platforms/exe-dev.md
@@ -129,6 +129,10 @@ For daemon runs, persist it in `~/.clawdbot/clawdbot.json`:
 }
 ```
 
+Notes:
+- Non-loopback binds require `gateway.auth.token` (or `CLAWDBOT_GATEWAY_TOKEN`).
+- `gateway.remote.token` is only for remote CLI calls; it does not enable local auth.
+
 Then point exe.dev’s proxy at `8080` (or whatever port you chose) and open your VM’s HTTPS URL:
 
 ```bash
diff --git a/src/cli/daemon-cli.ts b/src/cli/daemon-cli.ts
index 0e818246b..8bfc6c1f7 100644
--- a/src/cli/daemon-cli.ts
+++ b/src/cli/daemon-cli.ts
@@ -5,7 +5,13 @@ import {
   DEFAULT_GATEWAY_DAEMON_RUNTIME,
   isGatewayDaemonRuntime,
 } from "../commands/daemon-runtime.js";
-import { loadConfig, resolveGatewayPort } from "../config/config.js";
+import {
+  createConfigIO,
+  loadConfig,
+  resolveConfigPath,
+  resolveGatewayPort,
+  resolveStateDir,
+} from "../config/config.js";
 import { resolveIsNixMode } from "../config/paths.js";
 import {
   GATEWAY_LAUNCH_AGENT_LABEL,
@@ -17,11 +23,13 @@ import {
   findExtraGatewayServices,
   renderGatewayServiceCleanupHints,
 } from "../daemon/inspect.js";
+import { readLastGatewayErrorLine } from "../daemon/diagnostics.js";
 import { resolveGatewayLogPaths } from "../daemon/launchd.js";
 import { findLegacyGatewayServices } from "../daemon/legacy.js";
 import { resolveGatewayProgramArguments } from "../daemon/program-args.js";
 import { resolveGatewayService } from "../daemon/service.js";
 import { callGateway } from "../gateway/call.js";
+import { resolveGatewayBindHost } from "../gateway/net.js";
 import {
   formatPortDiagnostics,
   inspectPortUsage,
@@ -33,6 +41,22 @@ import { defaultRuntime } from "../runtime.js";
 import { createDefaultDeps } from "./deps.js";
 import { withProgress } from "./progress.js";
 
+type ConfigSummary = {
+  path: string;
+  exists: boolean;
+  valid: boolean;
+  issues?: Array<{ path: string; message: string }>;
+};
+
+type GatewayStatusSummary = {
+  bindMode: string;
+  bindHost: string | null;
+  port: number;
+  portSource: "service args" | "env/config";
+  probeUrl: string;
+  probeNote?: string;
+};
+
 type DaemonStatus = {
   service: {
     label: string;
@@ -42,6 +66,8 @@ type DaemonStatus = {
     command?: {
       programArguments: string[];
       workingDirectory?: string;
+      environment?: Record<string, string>;
+      sourcePath?: string;
     } | null;
     runtime?: {
       status?: string;
@@ -57,15 +83,29 @@ type DaemonStatus = {
       missingUnit?: boolean;
     };
   };
+  config?: {
+    cli: ConfigSummary;
+    daemon?: ConfigSummary;
+    mismatch?: boolean;
+  };
+  gateway?: GatewayStatusSummary;
   port?: {
     port: number;
     status: PortUsageStatus;
     listeners: PortListener[];
     hints: string[];
   };
+  portCli?: {
+    port: number;
+    status: PortUsageStatus;
+    listeners: PortListener[];
+    hints: string[];
+  };
+  lastError?: string;
   rpc?: {
     ok: boolean;
     error?: string;
+    url?: string;
   };
   legacyServices: Array<{ label: string; detail: string }>;
   extraServices: Array<{ label: string; detail: string; scope: string }>;
@@ -253,6 +293,15 @@ async function gatherDaemonStatus(opts: {
     deep: opts.deep,
   });
   const rpc = opts.probe ? await probeGatewayStatus(opts.rpc) : undefined;
+  let lastError: string | undefined;
+  if (
+    loaded &&
+    runtime?.status === "running" &&
+    portStatus &&
+    portStatus.status !== "busy"
+  ) {
+    lastError = (await readLastGatewayErrorLine(process.env)) ?? undefined;
+  }
 
   return {
     service: {
@@ -264,6 +313,7 @@ async function gatherDaemonStatus(opts: {
       runtime,
     },
     port: portStatus,
+    lastError,
     rpc,
     legacyServices,
     extraServices,
@@ -334,6 +384,28 @@ function printDaemonStatus(status: DaemonStatus, opts: { json: boolean }) {
       defaultRuntime.error(line);
     }
   }
+  if (
+    service.loaded &&
+    service.runtime?.status === "running" &&
+    status.port &&
+    status.port.status !== "busy"
+  ) {
+    defaultRuntime.error(
+      `Gateway port ${status.port.port} is not listening (service appears running).`,
+    );
+    if (status.lastError) {
+      defaultRuntime.error(`Last gateway error: ${status.lastError}`);
+    }
+    if (process.platform === "linux") {
+      defaultRuntime.error(
+        `Logs: journalctl --user -u ${GATEWAY_SYSTEMD_SERVICE_NAME}.service -n 200 --no-pager`,
+      );
+    } else if (process.platform === "darwin") {
+      const logs = resolveGatewayLogPaths(process.env);
+      defaultRuntime.error(`Logs: ${logs.stdoutPath}`);
+      defaultRuntime.error(`Errors: ${logs.stderrPath}`);
+    }
+  }
 
   if (legacyServices.length > 0) {
     defaultRuntime.error("Legacy Clawdis services detected:");
diff --git a/src/cli/gateway-cli.ts b/src/cli/gateway-cli.ts
index 814eef12b..e846b612c 100644
--- a/src/cli/gateway-cli.ts
+++ b/src/cli/gateway-cli.ts
@@ -4,6 +4,7 @@ import type { Command } from "commander";
 import {
   CONFIG_PATH_CLAWDBOT,
   loadConfig,
+  readConfigFileSnapshot,
   resolveGatewayPort,
 } from "../config/config.js";
 import {
@@ -70,6 +71,26 @@ function describeUnknownError(err: unknown): string {
   return "Unknown error";
 }
 
+function extractGatewayMiskeys(parsed: unknown): {
+  hasGatewayToken: boolean;
+  hasRemoteToken: boolean;
+} {
+  if (!parsed || typeof parsed !== "object") {
+    return { hasGatewayToken: false, hasRemoteToken: false };
+  }
+  const gateway = (parsed as Record<string, unknown>).gateway;
+  if (!gateway || typeof gateway !== "object") {
+    return { hasGatewayToken: false, hasRemoteToken: false };
+  }
+  const hasGatewayToken = "token" in (gateway as Record<string, unknown>);
+  const remote = (gateway as Record<string, unknown>).remote;
+  const hasRemoteToken =
+    remote && typeof remote === "object"
+      ? "token" in (remote as Record<string, unknown>)
+      : false;
+  return { hasGatewayToken, hasRemoteToken };
+}
+
 function renderGatewayServiceStopHints(): string[] {
   switch (process.platform) {
     case "darwin":
@@ -368,7 +389,7 @@ export function registerGatewayCli(program: Command) {
           );
         } else {
           defaultRuntime.error(
-            "Gateway start blocked: set gateway.mode=local (or pass --allow-unconfigured).",
+            `Gateway start blocked: set gateway.mode=local (current: ${mode ?? "unset"}) or pass --allow-unconfigured.`,
           );
         }
         defaultRuntime.exit(1);
@@ -390,6 +411,72 @@ export function registerGatewayCli(program: Command) {
         return;
       }
 
+      const snapshot = await readConfigFileSnapshot().catch(() => null);
+      const miskeys = extractGatewayMiskeys(snapshot?.parsed);
+      const authModeFromConfig = cfg.gateway?.auth?.mode;
+      const tokenValue =
+        opts.token ??
+        cfg.gateway?.auth?.token ??
+        process.env.CLAWDBOT_GATEWAY_TOKEN;
+      const passwordValue =
+        opts.password ??
+        cfg.gateway?.auth?.password ??
+        process.env.CLAWDBOT_GATEWAY_PASSWORD;
+      const resolvedAuthMode =
+        authMode ??
+        authModeFromConfig ??
+        (passwordValue ? "password" : tokenValue ? "token" : "none");
+      const authHints: string[] = [];
+      if (miskeys.hasGatewayToken) {
+        authHints.push(
+          'Found "gateway.token" in config. Use "gateway.auth.token" instead.',
+        );
+      }
+      if (miskeys.hasRemoteToken) {
+        authHints.push(
+          '"gateway.remote.token" is for remote CLI calls; it does not enable local gateway auth.',
+        );
+      }
+      if (resolvedAuthMode === "token" && !tokenValue) {
+        defaultRuntime.error(
+          [
+            "Gateway auth is set to token, but no token is configured.",
+            "Set gateway.auth.token (or CLAWDBOT_GATEWAY_TOKEN), or pass --token.",
+            ...authHints,
+          ]
+            .filter(Boolean)
+            .join("\n"),
+        );
+        defaultRuntime.exit(1);
+        return;
+      }
+      if (resolvedAuthMode === "password" && !passwordValue) {
+        defaultRuntime.error(
+          [
+            "Gateway auth is set to password, but no password is configured.",
+            "Set gateway.auth.password (or CLAWDBOT_GATEWAY_PASSWORD), or pass --password.",
+            ...authHints,
+          ]
+            .filter(Boolean)
+            .join("\n"),
+        );
+        defaultRuntime.exit(1);
+        return;
+      }
+      if (bind !== "loopback" && resolvedAuthMode === "none") {
+        defaultRuntime.error(
+          [
+            `Refusing to bind gateway to ${bind} without auth.`,
+            "Set gateway.auth.token (or CLAWDBOT_GATEWAY_TOKEN) or pass --token.",
+            ...authHints,
+          ]
+            .filter(Boolean)
+            .join("\n"),
+        );
+        defaultRuntime.exit(1);
+        return;
+      }
+
       try {
         await runGatewayLoop({
           runtime: defaultRuntime,
diff --git a/src/config/io.ts b/src/config/io.ts
index 9ce2f72e5..a1e97b0a1 100644
--- a/src/config/io.ts
+++ b/src/config/io.ts
@@ -59,6 +59,20 @@ export type ConfigIoDeps = {
   logger?: Pick<typeof console, "error" | "warn">;
 };
 
+function warnOnConfigMiskeys(
+  raw: unknown,
+  logger: Pick<typeof console, "warn">,
+): void {
+  if (!raw || typeof raw !== "object") return;
+  const gateway = (raw as Record<string, unknown>).gateway;
+  if (!gateway || typeof gateway !== "object") return;
+  if ("token" in (gateway as Record<string, unknown>)) {
+    logger.warn(
+      'Config uses "gateway.token". This key is ignored; use "gateway.auth.token" instead.',
+    );
+  }
+}
+
 function resolveConfigPathForDeps(deps: Required<ConfigIoDeps>): string {
   if (deps.configPath) return deps.configPath;
   return resolveConfigPath(deps.env, resolveStateDir(deps.env, deps.homedir));
@@ -106,6 +120,7 @@ export function createConfigIO(overrides: ConfigIoDeps = {}) {
       }
       const raw = deps.fs.readFileSync(configPath, "utf-8");
       const parsed = deps.json5.parse(raw);
+      warnOnConfigMiskeys(parsed, deps.logger);
       if (typeof parsed !== "object" || parsed === null) return {};
       const validated = ClawdbotSchema.safeParse(parsed);
       if (!validated.success) {
diff --git a/src/gateway/server.ts b/src/gateway/server.ts
index 6ab603f45..5f21151cd 100644
--- a/src/gateway/server.ts
+++ b/src/gateway/server.ts
@@ -464,7 +464,7 @@ export async function startGatewayServer(
   }
   if (!isLoopbackHost(bindHost) && authMode === "none") {
     throw new Error(
-      `refusing to bind gateway to ${bindHost}:${port} without auth (set gateway.auth or CLAWDBOT_GATEWAY_TOKEN)`,
+      `refusing to bind gateway to ${bindHost}:${port} without auth (set gateway.auth.token or CLAWDBOT_GATEWAY_TOKEN, or pass --token)`,
     );
   }