diff --git a/packages/cli/src/cli.ts b/packages/cli/src/cli.ts
index 2bb8e2095..9a6d55ae4 100644
--- a/packages/cli/src/cli.ts
+++ b/packages/cli/src/cli.ts
@@ -19,6 +19,7 @@ import { runSendCommand } from './commands/agent/send.js'
 import { runInspectCommand } from './commands/agent/inspect.js'
 import { runWaitCommand } from './commands/agent/wait.js'
 import { runAttachCommand } from './commands/agent/attach.js'
+import { runDoctorCommand } from './commands/doctor.js'
 import { withOutput } from './output/index.js'
 import { onboardCommand } from './commands/onboard.js'
 
@@ -192,6 +193,14 @@ export function createCli(): Command {
     )
     .action(withOutput(runDaemonRestartCommand))
 
+  program
+    .command('doctor')
+    .description('Diagnose your Paseo setup (agents, config, runtime)')
+    .option('--remote', 'Fetch diagnostics from the running daemon instead of checking locally')
+    .option('--json', 'Output in JSON format')
+    .option('--host <host>', 'Daemon host target (used with --remote)')
+    .action(withOutput(runDoctorCommand))
+
   // Advanced agent commands (less common operations)
   program.addCommand(createAgentCommand())
 
diff --git a/packages/cli/src/commands/doctor.ts b/packages/cli/src/commands/doctor.ts
new file mode 100644
index 000000000..b65e7562f
--- /dev/null
+++ b/packages/cli/src/commands/doctor.ts
@@ -0,0 +1,96 @@
+import type { Command } from 'commander'
+import {
+  runDoctorChecks,
+  type DoctorCheckResult,
+  type DoctorReport,
+} from '@getpaseo/server'
+import { getDaemonHost, resolveDaemonTarget } from '../utils/client.js'
+import type { CommandOptions, ListResult, OutputSchema } from '../output/index.js'
+
+interface DoctorRow {
+  check: string
+  status: string
+  detail: string
+}
+
+function statusIndicator(status: DoctorCheckResult['status']): string {
+  switch (status) {
+    case 'ok':
+      return 'ok'
+    case 'warn':
+      return 'warn'
+    case 'error':
+      return 'error'
+  }
+}
+
+function toDoctorRows(report: DoctorReport): DoctorRow[] {
+  return report.checks.map((c) => ({
+    check: c.label,
+    status: statusIndicator(c.status),
+    detail: c.detail,
+  }))
+}
+
+function createDoctorSchema(report: DoctorReport): OutputSchema<DoctorRow> {
+  return {
+    idField: 'check',
+    columns: [
+      { header: 'CHECK', field: 'check' },
+      {
+        header: 'STATUS',
+        field: 'status',
+        color: (value) => {
+          if (value === 'ok') return 'green'
+          if (value === 'warn') return 'yellow'
+          if (value === 'error') return 'red'
+          return undefined
+        },
+      },
+      { header: 'DETAIL', field: 'detail' },
+    ],
+    serialize: () => report,
+  }
+}
+
+async function fetchRemoteReport(host: string): Promise<DoctorReport> {
+  const target = resolveDaemonTarget(host)
+  const baseUrl =
+    target.type === 'tcp'
+      ? target.url.replace(/^ws:\/\//, 'http://').replace(/\/ws$/, '')
+      : null
+
+  if (!baseUrl) {
+    throw new Error('Remote doctor requires a TCP daemon target (not unix socket)')
+  }
+
+  const response = await fetch(`${baseUrl}/api/doctor`)
+  if (!response.ok) {
+    const text = await response.text().catch(() => '')
+    throw new Error(`Doctor endpoint returned ${response.status}: ${text}`)
+  }
+  return (await response.json()) as DoctorReport
+}
+
+export type DoctorResult = ListResult<DoctorRow>
+
+export async function runDoctorCommand(
+  options: CommandOptions,
+  _command: Command
+): Promise<DoctorResult> {
+  const remote = Boolean(options.remote)
+
+  let report: DoctorReport
+  if (remote) {
+    const host = getDaemonHost(options)
+    report = await fetchRemoteReport(host)
+  } else {
+    report = await runDoctorChecks()
+  }
+
+  return {
+    type: 'list',
+    data: toDoctorRows(report),
+    schema: createDoctorSchema(report),
+  }
+}
diff --git a/packages/server/src/server/bootstrap.ts b/packages/server/src/server/bootstrap.ts
index eddfc337e..83284ec88 100644
--- a/packages/server/src/server/bootstrap.ts
+++ b/packages/server/src/server/bootstrap.ts
@@ -71,6 +71,7 @@ import { loadOrCreateDaemonKeyPair } from "./daemon-keypair.js";
 import { startRelayTransport, type RelayTransportController } from "./relay-transport.js";
 import { getOrCreateServerId } from "./server-id.js";
 import { resolveDaemonVersion } from "./daemon-version.js";
+import { runDoctorChecks } from "./doctor/index.js";
 import type {
   AgentClient,
   AgentProvider,
@@ -248,6 +249,20 @@ export async function createPaseoDaemon(
     res.json({ status: "ok", timestamp: new Date().toISOString() });
   });
 
+  // Doctor diagnostic endpoint
+  app.get("/api/doctor", async (_req, res) => {
+    try {
+      const report = await runDoctorChecks({
+        paseoHome: config.paseoHome,
+        version: daemonVersion,
+      });
+      res.json(report);
+    } catch (err) {
+      const message = err instanceof Error ? err.message : String(err);
+      res.status(500).json({ error: message });
+    }
+  });
+
   app.get("/api/files/download", async (req, res) => {
     const token =
       typeof req.query.token === "string" && req.query.token.trim().length > 0
diff --git a/packages/server/src/server/doctor/checks/config-checks.ts b/packages/server/src/server/doctor/checks/config-checks.ts
new file mode 100644
index 000000000..196ee4db8
--- /dev/null
+++ b/packages/server/src/server/doctor/checks/config-checks.ts
@@ -0,0 +1,72 @@
+import { loadPersistedConfig } from "../../persisted-config.js";
+import type { DoctorCheckResult } from "../types.js";
+
+/**
+ * Validate that a listen string is parseable as a valid listen target.
+ * Inline check to avoid importing from bootstrap.ts (which has heavy transitive deps).
+ */
+function isValidListenString(listen: string): boolean {
+  // Named pipe
+  if (listen.startsWith("\\\\.\\pipe\\") || listen.startsWith("pipe://")) return true;
+  // Unix socket
+  if (listen.startsWith("/") || listen.startsWith("~") || listen.includes(".sock")) return true;
+  if (listen.startsWith("unix://")) return true;
+  // TCP host:port
+  if (listen.includes(":")) {
+    const port = parseInt(listen.split(":")[1]!, 10);
+    return Number.isFinite(port);
+  }
+  // Just a port
+  return Number.isFinite(parseInt(listen, 10));
+}
+
+function checkConfigValid(paseoHome: string): DoctorCheckResult {
+  try {
+    loadPersistedConfig(paseoHome);
+    return {
+      id: "config.valid",
+      label: "Config file",
+      status: "ok",
+      detail: "Valid",
+    };
+  } catch (err) {
+    return {
+      id: "config.valid",
+      label: "Config file",
+      status: "error",
+      detail: err instanceof Error ? err.message : String(err),
+    };
+  }
+}
+
+function checkListenAddress(paseoHome: string): DoctorCheckResult {
+  try {
+    const config = loadPersistedConfig(paseoHome);
+    const listen = config.daemon?.listen ?? "127.0.0.1:6767";
+    if (!isValidListenString(listen)) {
+      return {
+        id: "config.listen",
+        label: "Listen address",
+        status: "error",
+        detail: `Malformed listen address: ${listen}`,
+      };
+    }
+    return {
+      id: "config.listen",
+      label: "Listen address",
+      status: "ok",
+      detail: listen,
+    };
+  } catch (err) {
+    return {
+      id: "config.listen",
+      label: "Listen address",
+      status: "error",
+      detail: err instanceof Error ? err.message : String(err),
+    };
+  }
+}
+
+export async function runConfigChecks(paseoHome: string): Promise<DoctorCheckResult[]> {
+  return [checkConfigValid(paseoHome), checkListenAddress(paseoHome)];
+}
diff --git a/packages/server/src/server/doctor/checks/provider-checks.ts b/packages/server/src/server/doctor/checks/provider-checks.ts
new file mode 100644
index 000000000..9fb9814fa
--- /dev/null
+++ b/packages/server/src/server/doctor/checks/provider-checks.ts
@@ -0,0 +1,87 @@
+import { execFileSync } from "node:child_process";
+
+import type { DoctorCheckResult } from "../types.js";
+
+interface ProviderDef {
+  name: string;
+  command: string;
+  label: string;
+}
+
+const PROVIDERS: ProviderDef[] = [
+  { name: "claude", command: "claude", label: "Claude CLI" },
+  { name: "codex", command: "codex", label: "Codex CLI" },
+  { name: "opencode", command: "opencode", label: "OpenCode CLI" },
+];
+
+function whichCommand(command: string): string | null {
+  try {
+    return execFileSync("which", [command], { encoding: "utf8" }).trim() || null;
+  } catch {
+    return null;
+  }
+}
+
+function getVersion(binaryPath: string): string | null {
+  try {
+    return execFileSync(binaryPath, ["--version"], { encoding: "utf8" }).trim() || null;
+  } catch {
+    return null;
+  }
+}
+
+function checkBinary(provider: ProviderDef): DoctorCheckResult {
+  const binaryPath = whichCommand(provider.command);
+  if (binaryPath) {
+    return {
+      id: `provider.${provider.name}.binary`,
+      label: provider.label,
+      status: "ok",
+      detail: binaryPath,
+    };
+  }
+  return {
+    id: `provider.${provider.name}.binary`,
+    label: provider.label,
+    status: "error",
+    detail: "Not found in PATH",
+  };
+}
+
+function checkVersion(provider: ProviderDef): DoctorCheckResult {
+  const binaryPath = whichCommand(provider.command);
+  if (!binaryPath) {
+    return {
+      id: `provider.${provider.name}.version`,
+      label: `${provider.label} version`,
+      status: "error",
+      detail: "Binary not found",
+    };
+  }
+
+  const version = getVersion(binaryPath);
+  if (version) {
+    return {
+      id: `provider.${provider.name}.version`,
+      label: `${provider.label} version`,
+      status: "ok",
+      detail: version,
+    };
+  }
+
+  return {
+    id: `provider.${provider.name}.version`,
+    label: `${provider.label} version`,
+    status: "warn",
+    detail: "Installed but version could not be parsed",
+  };
+}
+
+export async function runProviderChecks(): Promise<DoctorCheckResult[]> {
+  const results: DoctorCheckResult[] = [];
+  for (const provider of PROVIDERS) {
+    results.push(checkBinary(provider));
+    results.push(checkVersion(provider));
+  }
+  return results;
+}
diff --git a/packages/server/src/server/doctor/checks/runtime-checks.ts b/packages/server/src/server/doctor/checks/runtime-checks.ts
new file mode 100644
index 000000000..a82bdef89
--- /dev/null
+++ b/packages/server/src/server/doctor/checks/runtime-checks.ts
@@ -0,0 +1,43 @@
+import { resolveDaemonVersion } from "../../daemon-version.js";
+import type { DoctorCheckResult } from "../types.js";
+
+function checkNodeVersion(): DoctorCheckResult {
+  return {
+    id: "runtime.node",
+    label: "Node.js",
+    status: "ok",
+    detail: process.version,
+  };
+}
+
+function checkPaseoVersion(version?: string): DoctorCheckResult {
+  const resolved = version ?? tryResolveDaemonVersion();
+  if (resolved) {
+    return {
+      id: "runtime.paseo",
+      label: "Paseo daemon",
+      status: "ok",
+      detail: resolved,
+    };
+  }
+  return {
+    id: "runtime.paseo",
+    label: "Paseo daemon",
+    status: "error",
+    detail: "Version unknown",
+  };
+}
+
+function tryResolveDaemonVersion(): string | null {
+  try {
+    return resolveDaemonVersion();
+  } catch {
+    return null;
+  }
+}
+
+export async function runRuntimeChecks(options?: {
+  version?: string;
+}): Promise<DoctorCheckResult[]> {
+  return [checkNodeVersion(), checkPaseoVersion(options?.version)];
+}
diff --git a/packages/server/src/server/doctor/index.ts b/packages/server/src/server/doctor/index.ts
new file mode 100644
index 000000000..25bc33474
--- /dev/null
+++ b/packages/server/src/server/doctor/index.ts
@@ -0,0 +1,2 @@
+export { runDoctorChecks } from "./run-doctor-checks.js";
+export type { CheckStatus, DoctorCheckResult, DoctorReport } from "./types.js";
diff --git a/packages/server/src/server/doctor/run-doctor-checks.test.ts b/packages/server/src/server/doctor/run-doctor-checks.test.ts
new file mode 100644
index 000000000..3bfd6b567
--- /dev/null
+++ b/packages/server/src/server/doctor/run-doctor-checks.test.ts
@@ -0,0 +1,86 @@
+import { describe, it, expect } from "vitest";
+import { runDoctorChecks } from "./run-doctor-checks.js";
+import type { DoctorReport, DoctorCheckResult } from "./types.js";
+
+describe("runDoctorChecks", () => {
+  it("returns a valid DoctorReport shape", async () => {
+    const report = await runDoctorChecks();
+
+    expect(report).toHaveProperty("checks");
+    expect(report).toHaveProperty("summary");
+    expect(report).toHaveProperty("timestamp");
+    expect(Array.isArray(report.checks)).toBe(true);
+  });
+
+  it("has summary counts matching checks array", async () => {
+    const report = await runDoctorChecks();
+
+    const okCount = report.checks.filter((c) => c.status === "ok").length;
+    const warnCount = report.checks.filter((c) => c.status === "warn").length;
+    const errorCount = report.checks.filter((c) => c.status === "error").length;
+
+    expect(report.summary.ok).toBe(okCount);
+    expect(report.summary.warn).toBe(warnCount);
+    expect(report.summary.error).toBe(errorCount);
+    expect(okCount + warnCount + errorCount).toBe(report.checks.length);
+  });
+
+  it("has a valid ISO timestamp", async () => {
+    const report = await runDoctorChecks();
+    const parsed = new Date(report.timestamp);
+    expect(parsed.toISOString()).toBe(report.timestamp);
+  });
+
+  it("each check has the expected shape", async () => {
+    const report = await runDoctorChecks();
+
+    for (const check of report.checks) {
+      expect(typeof check.id).toBe("string");
+      expect(check.id.length).toBeGreaterThan(0);
+      expect(typeof check.label).toBe("string");
+      expect(check.label.length).toBeGreaterThan(0);
+      expect(["ok", "warn", "error"]).toContain(check.status);
+      expect(typeof check.detail).toBe("string");
+      expect(check.detail.length).toBeGreaterThan(0);
+    }
+  });
+
+  it("includes expected check IDs", async () => {
+    const report = await runDoctorChecks();
+    const ids = report.checks.map((c) => c.id);
+
+    // Provider checks
+    expect(ids).toContain("provider.claude.binary");
+    expect(ids).toContain("provider.claude.version");
+    expect(ids).toContain("provider.codex.binary");
+    expect(ids).toContain("provider.codex.version");
+    expect(ids).toContain("provider.opencode.binary");
+    expect(ids).toContain("provider.opencode.version");
+
+    // Config checks
+    expect(ids).toContain("config.valid");
+    expect(ids).toContain("config.listen");
+
+    // Runtime checks
+    expect(ids).toContain("runtime.node");
+    expect(ids).toContain("runtime.paseo");
+  });
+
+  it("runtime.node reports the current Node version", async () => {
+    const report = await runDoctorChecks();
+    const nodeCheck = report.checks.find((c) => c.id === "runtime.node");
+
+    expect(nodeCheck).toBeDefined();
+    expect(nodeCheck!.status).toBe("ok");
+    expect(nodeCheck!.detail).toBe(process.version);
+  });
+
+  it("accepts a custom version option", async () => {
+    const report = await runDoctorChecks({ version: "1.2.3-test" });
+    const paseoCheck = report.checks.find((c) => c.id === "runtime.paseo");
+
+    expect(paseoCheck).toBeDefined();
+    expect(paseoCheck!.status).toBe("ok");
+    expect(paseoCheck!.detail).toBe("1.2.3-test");
+  });
+});
diff --git a/packages/server/src/server/doctor/run-doctor-checks.ts b/packages/server/src/server/doctor/run-doctor-checks.ts
new file mode 100644
index 000000000..8b8e7a1a1
--- /dev/null
+++ b/packages/server/src/server/doctor/run-doctor-checks.ts
@@ -0,0 +1,26 @@
+import { resolvePaseoHome } from "../paseo-home.js";
+import { runProviderChecks } from "./checks/provider-checks.js";
+import { runConfigChecks } from "./checks/config-checks.js";
+import { runRuntimeChecks } from "./checks/runtime-checks.js";
+import type { DoctorReport } from "./types.js";
+
+export async function runDoctorChecks(options?: {
+  paseoHome?: string;
+  version?: string;
+}): Promise<DoctorReport> {
+  const paseoHome = options?.paseoHome ?? resolvePaseoHome();
+
+  const checks = [
+    ...(await runProviderChecks()),
+    ...(await runConfigChecks(paseoHome)),
+    ...(await runRuntimeChecks({ version: options?.version })),
+  ];
+
+  const summary = {
+    ok: checks.filter((c) => c.status === "ok").length,
+    warn: checks.filter((c) => c.status === "warn").length,
+    error: checks.filter((c) => c.status === "error").length,
+  };
+
+  return { checks, summary, timestamp: new Date().toISOString() };
+}
diff --git a/packages/server/src/server/doctor/types.ts b/packages/server/src/server/doctor/types.ts
new file mode 100644
index 000000000..86b5be4dd
--- /dev/null
+++ b/packages/server/src/server/doctor/types.ts
@@ -0,0 +1,14 @@
+export type CheckStatus = "ok" | "warn" | "error";
+
+export interface DoctorCheckResult {
+  id: string;
+  label: string;
+  status: CheckStatus;
+  detail: string;
+}
+
+export interface DoctorReport {
+  checks: DoctorCheckResult[];
+  summary: { ok: number; warn: number; error: number };
+  timestamp: string;
+}
diff --git a/packages/server/src/server/exports.ts b/packages/server/src/server/exports.ts
index dee16d888..88dedef55 100644
--- a/packages/server/src/server/exports.ts
+++ b/packages/server/src/server/exports.ts
@@ -23,6 +23,14 @@ export {
   type SherpaLoaderEnvResolution,
 } from "./speech/providers/local/sherpa/sherpa-runtime-env.js";
 
+// Doctor health check
+export {
+  runDoctorChecks,
+  type CheckStatus,
+  type DoctorCheckResult,
+  type DoctorReport,
+} from "./doctor/index.js";
+
 // Agent SDK types for CLI commands
 export type {
   AgentMode,