Add CLI package, config file support, and workspace setup

Add cli/ package with initial scaffolding. Add config-schema to shared
package for typed configuration. Add server config-file loader for
paperclip.config.ts support. Register cli in pnpm workspace. Add
.paperclip/ and .pnpm-store/ to gitignore. Minor Companies page fix.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

cli/src/checks/config-check.ts

@@ -0,0 +1,33 @@
+import { readConfig, configExists, resolveConfigPath } from "../config/store.js";
+import type { CheckResult } from "./index.js";
+
+export function configCheck(configPath?: string): CheckResult {
+  const filePath = resolveConfigPath(configPath);
+
+  if (!configExists(configPath)) {
+    return {
+      name: "Config file",
+      status: "fail",
+      message: `Config file not found at ${filePath}`,
+      canRepair: false,
+      repairHint: "Run `paperclip onboard` to create one",
+    };
+  }
+
+  try {
+    readConfig(configPath);
+    return {
+      name: "Config file",
+      status: "pass",
+      message: `Valid config at ${filePath}`,
+    };
+  } catch (err) {
+    return {
+      name: "Config file",
+      status: "fail",
+      message: `Invalid config: ${err instanceof Error ? err.message : String(err)}`,
+      canRepair: false,
+      repairHint: "Run `paperclip onboard` to recreate",
+    };
+  }
+}

cli/src/checks/database-check.ts

@@ -0,0 +1,57 @@
+import fs from "node:fs";
+import path from "node:path";
+import type { PaperclipConfig } from "../config/schema.js";
+import type { CheckResult } from "./index.js";
+
+export async function databaseCheck(config: PaperclipConfig): Promise<CheckResult> {
+  if (config.database.mode === "postgres") {
+    if (!config.database.connectionString) {
+      return {
+        name: "Database",
+        status: "fail",
+        message: "PostgreSQL mode selected but no connection string configured",
+        canRepair: false,
+        repairHint: "Run `paperclip configure --section database`",
+      };
+    }
+
+    try {
+      const { createDb } = await import("@paperclip/db");
+      const db = createDb(config.database.connectionString);
+      await db.execute("SELECT 1");
+      return {
+        name: "Database",
+        status: "pass",
+        message: "PostgreSQL connection successful",
+      };
+    } catch (err) {
+      return {
+        name: "Database",
+        status: "fail",
+        message: `Cannot connect to PostgreSQL: ${err instanceof Error ? err.message : String(err)}`,
+        canRepair: false,
+        repairHint: "Check your connection string and ensure PostgreSQL is running",
+      };
+    }
+  }
+
+  // PGlite mode — check data dir
+  const dataDir = path.resolve(config.database.pgliteDataDir);
+  if (!fs.existsSync(dataDir)) {
+    return {
+      name: "Database",
+      status: "warn",
+      message: `PGlite data directory does not exist: ${dataDir}`,
+      canRepair: true,
+      repair: () => {
+        fs.mkdirSync(dataDir, { recursive: true });
+      },
+    };
+  }
+
+  return {
+    name: "Database",
+    status: "pass",
+    message: `PGlite data directory exists: ${dataDir}`,
+  };
+}

cli/src/checks/index.ts

@@ -0,0 +1,14 @@
+export interface CheckResult {
+  name: string;
+  status: "pass" | "warn" | "fail";
+  message: string;
+  canRepair?: boolean;
+  repair?: () => void | Promise<void>;
+  repairHint?: string;
+}
+
+export { configCheck } from "./config-check.js";
+export { databaseCheck } from "./database-check.js";
+export { llmCheck } from "./llm-check.js";
+export { logCheck } from "./log-check.js";
+export { portCheck } from "./port-check.js";

cli/src/checks/llm-check.ts

@@ -0,0 +1,86 @@
+import type { PaperclipConfig } from "../config/schema.js";
+import type { CheckResult } from "./index.js";
+
+export async function llmCheck(config: PaperclipConfig): Promise<CheckResult> {
+  if (!config.llm) {
+    return {
+      name: "LLM provider",
+      status: "warn",
+      message: "No LLM provider configured",
+      canRepair: false,
+      repairHint: "Run `paperclip configure --section llm` to set one up",
+    };
+  }
+
+  if (!config.llm.apiKey) {
+    return {
+      name: "LLM provider",
+      status: "warn",
+      message: `${config.llm.provider} configured but no API key set`,
+      canRepair: false,
+      repairHint: "Run `paperclip configure --section llm`",
+    };
+  }
+
+  try {
+    if (config.llm.provider === "claude") {
+      const res = await fetch("https://api.anthropic.com/v1/messages", {
+        method: "POST",
+        headers: {
+          "x-api-key": config.llm.apiKey,
+          "anthropic-version": "2023-06-01",
+          "content-type": "application/json",
+        },
+        body: JSON.stringify({
+          model: "claude-sonnet-4-5-20250929",
+          max_tokens: 1,
+          messages: [{ role: "user", content: "hi" }],
+        }),
+      });
+      if (res.ok || res.status === 400) {
+        return { name: "LLM provider", status: "pass", message: "Claude API key is valid" };
+      }
+      if (res.status === 401) {
+        return {
+          name: "LLM provider",
+          status: "fail",
+          message: "Claude API key is invalid (401)",
+          canRepair: false,
+          repairHint: "Run `paperclip configure --section llm`",
+        };
+      }
+      return {
+        name: "LLM provider",
+        status: "warn",
+        message: `Claude API returned status ${res.status}`,
+      };
+    } else {
+      const res = await fetch("https://api.openai.com/v1/models", {
+        headers: { Authorization: `Bearer ${config.llm.apiKey}` },
+      });
+      if (res.ok) {
+        return { name: "LLM provider", status: "pass", message: "OpenAI API key is valid" };
+      }
+      if (res.status === 401) {
+        return {
+          name: "LLM provider",
+          status: "fail",
+          message: "OpenAI API key is invalid (401)",
+          canRepair: false,
+          repairHint: "Run `paperclip configure --section llm`",
+        };
+      }
+      return {
+        name: "LLM provider",
+        status: "warn",
+        message: `OpenAI API returned status ${res.status}`,
+      };
+    }
+  } catch {
+    return {
+      name: "LLM provider",
+      status: "warn",
+      message: "Could not reach API to validate key",
+    };
+  }
+}

cli/src/checks/log-check.ts

@@ -0,0 +1,37 @@
+import fs from "node:fs";
+import path from "node:path";
+import type { PaperclipConfig } from "../config/schema.js";
+import type { CheckResult } from "./index.js";
+
+export function logCheck(config: PaperclipConfig): CheckResult {
+  const logDir = path.resolve(config.logging.logDir);
+
+  if (!fs.existsSync(logDir)) {
+    return {
+      name: "Log directory",
+      status: "warn",
+      message: `Log directory does not exist: ${logDir}`,
+      canRepair: true,
+      repair: () => {
+        fs.mkdirSync(logDir, { recursive: true });
+      },
+    };
+  }
+
+  try {
+    fs.accessSync(logDir, fs.constants.W_OK);
+    return {
+      name: "Log directory",
+      status: "pass",
+      message: `Log directory is writable: ${logDir}`,
+    };
+  } catch {
+    return {
+      name: "Log directory",
+      status: "fail",
+      message: `Log directory is not writable: ${logDir}`,
+      canRepair: false,
+      repairHint: "Check file permissions on the log directory",
+    };
+  }
+}

cli/src/checks/port-check.ts

@@ -0,0 +1,24 @@
+import type { PaperclipConfig } from "../config/schema.js";
+import { checkPort } from "../utils/net.js";
+import type { CheckResult } from "./index.js";
+
+export async function portCheck(config: PaperclipConfig): Promise<CheckResult> {
+  const port = config.server.port;
+  const result = await checkPort(port);
+
+  if (result.available) {
+    return {
+      name: "Server port",
+      status: "pass",
+      message: `Port ${port} is available`,
+    };
+  }
+
+  return {
+    name: "Server port",
+    status: "warn",
+    message: result.error ?? `Port ${port} is not available`,
+    canRepair: false,
+    repairHint: `Check what's using port ${port} with: lsof -i :${port}`,
+  };
+}

cli/src/commands/configure.ts

@@ -0,0 +1,113 @@
+import * as p from "@clack/prompts";
+import pc from "picocolors";
+import { readConfig, writeConfig, configExists } from "../config/store.js";
+import type { PaperclipConfig } from "../config/schema.js";
+import { promptDatabase } from "../prompts/database.js";
+import { promptLlm } from "../prompts/llm.js";
+import { promptLogging } from "../prompts/logging.js";
+import { promptServer } from "../prompts/server.js";
+
+type Section = "llm" | "database" | "logging" | "server";
+
+const SECTION_LABELS: Record<Section, string> = {
+  llm: "LLM Provider",
+  database: "Database",
+  logging: "Logging",
+  server: "Server",
+};
+
+export async function configure(opts: {
+  config?: string;
+  section?: string;
+}): Promise<void> {
+  p.intro(pc.bgCyan(pc.black(" paperclip configure ")));
+
+  if (!configExists(opts.config)) {
+    p.log.error("No config file found. Run `paperclip onboard` first.");
+    p.outro("");
+    return;
+  }
+
+  const config = readConfig(opts.config);
+  if (!config) {
+    p.log.error("Could not read config file. Run `paperclip onboard` to recreate.");
+    p.outro("");
+    return;
+  }
+
+  let section: Section | undefined = opts.section as Section | undefined;
+
+  if (section && !SECTION_LABELS[section]) {
+    p.log.error(`Unknown section: ${section}. Choose from: ${Object.keys(SECTION_LABELS).join(", ")}`);
+    p.outro("");
+    return;
+  }
+
+  // Section selection loop
+  let continueLoop = true;
+  while (continueLoop) {
+    if (!section) {
+      const choice = await p.select({
+        message: "Which section do you want to configure?",
+        options: Object.entries(SECTION_LABELS).map(([value, label]) => ({
+          value: value as Section,
+          label,
+        })),
+      });
+
+      if (p.isCancel(choice)) {
+        p.cancel("Configuration cancelled.");
+        return;
+      }
+
+      section = choice;
+    }
+
+    p.log.step(pc.bold(SECTION_LABELS[section]));
+
+    switch (section) {
+      case "database":
+        config.database = await promptDatabase();
+        break;
+      case "llm": {
+        const llm = await promptLlm();
+        if (llm) {
+          config.llm = llm;
+        } else {
+          delete config.llm;
+        }
+        break;
+      }
+      case "logging":
+        config.logging = await promptLogging();
+        break;
+      case "server":
+        config.server = await promptServer();
+        break;
+    }
+
+    config.$meta.updatedAt = new Date().toISOString();
+    config.$meta.source = "configure";
+
+    writeConfig(config, opts.config);
+    p.log.success(`${SECTION_LABELS[section]} configuration updated.`);
+
+    // If section was provided via CLI flag, don't loop
+    if (opts.section) {
+      continueLoop = false;
+    } else {
+      const another = await p.confirm({
+        message: "Configure another section?",
+        initialValue: false,
+      });
+
+      if (p.isCancel(another) || !another) {
+        continueLoop = false;
+      } else {
+        section = undefined; // Reset to show picker again
+      }
+    }
+  }
+
+  p.outro("Configuration saved.");
+}

cli/src/commands/doctor.ts

@@ -0,0 +1,120 @@
+import * as p from "@clack/prompts";
+import pc from "picocolors";
+import { readConfig } from "../config/store.js";
+import {
+  configCheck,
+  databaseCheck,
+  llmCheck,
+  logCheck,
+  portCheck,
+  type CheckResult,
+} from "../checks/index.js";
+
+const STATUS_ICON = {
+  pass: pc.green("✓"),
+  warn: pc.yellow("!"),
+  fail: pc.red("✗"),
+} as const;
+
+export async function doctor(opts: {
+  config?: string;
+  repair?: boolean;
+  yes?: boolean;
+}): Promise<void> {
+  p.intro(pc.bgCyan(pc.black(" paperclip doctor ")));
+
+  const results: CheckResult[] = [];
+
+  // 1. Config check (must pass before others)
+  const cfgResult = configCheck(opts.config);
+  results.push(cfgResult);
+  printResult(cfgResult);
+
+  if (cfgResult.status === "fail") {
+    printSummary(results);
+    return;
+  }
+
+  const config = readConfig(opts.config)!;
+
+  // 2. Database check
+  const dbResult = await databaseCheck(config);
+  results.push(dbResult);
+  printResult(dbResult);
+  await maybeRepair(dbResult, opts);
+
+  // 3. LLM check
+  const llmResult = await llmCheck(config);
+  results.push(llmResult);
+  printResult(llmResult);
+
+  // 4. Log directory check
+  const logResult = logCheck(config);
+  results.push(logResult);
+  printResult(logResult);
+  await maybeRepair(logResult, opts);
+
+  // 5. Port check
+  const portResult = await portCheck(config);
+  results.push(portResult);
+  printResult(portResult);
+
+  // Summary
+  printSummary(results);
+}
+
+function printResult(result: CheckResult): void {
+  const icon = STATUS_ICON[result.status];
+  p.log.message(`${icon} ${pc.bold(result.name)}: ${result.message}`);
+  if (result.status !== "pass" && result.repairHint) {
+    p.log.message(`  ${pc.dim(result.repairHint)}`);
+  }
+}
+
+async function maybeRepair(
+  result: CheckResult,
+  opts: { repair?: boolean; yes?: boolean },
+): Promise<void> {
+  if (result.status === "pass" || !result.canRepair || !result.repair) return;
+  if (!opts.repair) return;
+
+  let shouldRepair = opts.yes;
+  if (!shouldRepair) {
+    const answer = await p.confirm({
+      message: `Repair "${result.name}"?`,
+      initialValue: true,
+    });
+    if (p.isCancel(answer)) return;
+    shouldRepair = answer;
+  }
+
+  if (shouldRepair) {
+    try {
+      await result.repair();
+      p.log.success(`Repaired: ${result.name}`);
+    } catch (err) {
+      p.log.error(`Repair failed: ${err instanceof Error ? err.message : String(err)}`);
+    }
+  }
+}
+
+function printSummary(results: CheckResult[]): void {
+  const passed = results.filter((r) => r.status === "pass").length;
+  const warned = results.filter((r) => r.status === "warn").length;
+  const failed = results.filter((r) => r.status === "fail").length;
+
+  const parts: string[] = [];
+  parts.push(pc.green(`${passed} passed`));
+  if (warned) parts.push(pc.yellow(`${warned} warnings`));
+  if (failed) parts.push(pc.red(`${failed} failed`));
+
+  p.note(parts.join(", "), "Summary");
+
+  if (failed > 0) {
+    p.outro(pc.red("Some checks failed. Fix the issues above and re-run doctor."));
+  } else if (warned > 0) {
+    p.outro(pc.yellow("All critical checks passed with some warnings."));
+  } else {
+    p.outro(pc.green("All checks passed!"));
+  }
+}

cli/src/commands/onboard.ts

@@ -0,0 +1,127 @@
+import * as p from "@clack/prompts";
+import pc from "picocolors";
+import { configExists, readConfig, writeConfig } from "../config/store.js";
+import type { PaperclipConfig } from "../config/schema.js";
+import { promptDatabase } from "../prompts/database.js";
+import { promptLlm } from "../prompts/llm.js";
+import { promptLogging } from "../prompts/logging.js";
+import { promptServer } from "../prompts/server.js";
+
+export async function onboard(opts: { config?: string }): Promise<void> {
+  p.intro(pc.bgCyan(pc.black(" paperclip onboard ")));
+
+  // Check for existing config
+  if (configExists(opts.config)) {
+    const existing = readConfig(opts.config);
+    if (existing) {
+      const overwrite = await p.confirm({
+        message: "A config file already exists. Overwrite it?",
+        initialValue: false,
+      });
+
+      if (p.isCancel(overwrite) || !overwrite) {
+        p.cancel("Keeping existing configuration.");
+        return;
+      }
+    }
+  }
+
+  // Database
+  p.log.step(pc.bold("Database"));
+  const database = await promptDatabase();
+
+  if (database.mode === "postgres" && database.connectionString) {
+    const s = p.spinner();
+    s.start("Testing database connection...");
+    try {
+      const { createDb } = await import("@paperclip/db");
+      const db = createDb(database.connectionString);
+      await db.execute("SELECT 1");
+      s.stop("Database connection successful");
+    } catch (err) {
+      s.stop(pc.yellow("Could not connect to database — you can fix this later with `paperclip doctor`"));
+    }
+  }
+
+  // LLM
+  p.log.step(pc.bold("LLM Provider"));
+  const llm = await promptLlm();
+
+  if (llm?.apiKey) {
+    const s = p.spinner();
+    s.start("Validating API key...");
+    try {
+      if (llm.provider === "claude") {
+        const res = await fetch("https://api.anthropic.com/v1/messages", {
+          method: "POST",
+          headers: {
+            "x-api-key": llm.apiKey,
+            "anthropic-version": "2023-06-01",
+            "content-type": "application/json",
+          },
+          body: JSON.stringify({
+            model: "claude-sonnet-4-5-20250929",
+            max_tokens: 1,
+            messages: [{ role: "user", content: "hi" }],
+          }),
+        });
+        if (res.ok || res.status === 400) {
+          s.stop("API key is valid");
+        } else if (res.status === 401) {
+          s.stop(pc.yellow("API key appears invalid — you can update it later"));
+        } else {
+          s.stop(pc.yellow("Could not validate API key — continuing anyway"));
+        }
+      } else {
+        const res = await fetch("https://api.openai.com/v1/models", {
+          headers: { Authorization: `Bearer ${llm.apiKey}` },
+        });
+        if (res.ok) {
+          s.stop("API key is valid");
+        } else if (res.status === 401) {
+          s.stop(pc.yellow("API key appears invalid — you can update it later"));
+        } else {
+          s.stop(pc.yellow("Could not validate API key — continuing anyway"));
+        }
+      }
+    } catch {
+      s.stop(pc.yellow("Could not reach API — continuing anyway"));
+    }
+  }
+
+  // Logging
+  p.log.step(pc.bold("Logging"));
+  const logging = await promptLogging();
+
+  // Server
+  p.log.step(pc.bold("Server"));
+  const server = await promptServer();
+
+  // Assemble and write config
+  const config: PaperclipConfig = {
+    $meta: {
+      version: 1,
+      updatedAt: new Date().toISOString(),
+      source: "onboard",
+    },
+    ...(llm && { llm }),
+    database,
+    logging,
+    server,
+  };
+
+  writeConfig(config, opts.config);
+
+  p.note(
+    [
+      `Database: ${database.mode}`,
+      llm ? `LLM: ${llm.provider}` : "LLM: not configured",
+      `Logging: ${logging.mode} → ${logging.logDir}`,
+      `Server: port ${server.port}`,
+    ].join("\n"),
+    "Configuration saved",
+  );
+
+  p.log.info(`Run ${pc.cyan("pnpm paperclip doctor")} to verify your setup.`);
+  p.outro("You're all set!");
+}

cli/src/config/schema.ts

@@ -0,0 +1,14 @@
+export {
+  paperclipConfigSchema,
+  configMetaSchema,
+  llmConfigSchema,
+  databaseConfigSchema,
+  loggingConfigSchema,
+  serverConfigSchema,
+  type PaperclipConfig,
+  type LlmConfig,
+  type DatabaseConfig,
+  type LoggingConfig,
+  type ServerConfig,
+  type ConfigMeta,
+} from "@paperclip/shared";

cli/src/config/store.ts

@@ -0,0 +1,42 @@
+import fs from "node:fs";
+import path from "node:path";
+import { paperclipConfigSchema, type PaperclipConfig } from "./schema.js";
+
+const DEFAULT_CONFIG_PATH = ".paperclip/config.json";
+
+export function resolveConfigPath(overridePath?: string): string {
+  if (overridePath) return path.resolve(overridePath);
+  if (process.env.PAPERCLIP_CONFIG) return path.resolve(process.env.PAPERCLIP_CONFIG);
+  return path.resolve(process.cwd(), DEFAULT_CONFIG_PATH);
+}
+
+export function readConfig(configPath?: string): PaperclipConfig | null {
+  const filePath = resolveConfigPath(configPath);
+  if (!fs.existsSync(filePath)) return null;
+  const raw = JSON.parse(fs.readFileSync(filePath, "utf-8"));
+  return paperclipConfigSchema.parse(raw);
+}
+
+export function writeConfig(
+  config: PaperclipConfig,
+  configPath?: string,
+): void {
+  const filePath = resolveConfigPath(configPath);
+  const dir = path.dirname(filePath);
+  fs.mkdirSync(dir, { recursive: true });
+
+  // Backup existing config before overwriting
+  if (fs.existsSync(filePath)) {
+    const backupPath = filePath + ".backup";
+    fs.copyFileSync(filePath, backupPath);
+    fs.chmodSync(backupPath, 0o600);
+  }
+
+  fs.writeFileSync(filePath, JSON.stringify(config, null, 2) + "\n", {
+    mode: 0o600,
+  });
+}
+
+export function configExists(configPath?: string): boolean {
+  return fs.existsSync(resolveConfigPath(configPath));
+}

cli/src/index.ts

@@ -0,0 +1,36 @@
+#!/usr/bin/env node
+import { Command } from "commander";
+import { onboard } from "./commands/onboard.js";
+import { doctor } from "./commands/doctor.js";
+import { configure } from "./commands/configure.js";
+
+const program = new Command();
+
+program
+  .name("paperclip")
+  .description("Paperclip CLI — setup, diagnose, and configure your instance")
+  .version("0.0.1");
+
+program
+  .command("onboard")
+  .description("Interactive first-run setup wizard")
+  .option("-c, --config <path>", "Path to config file")
+  .action(onboard);
+
+program
+  .command("doctor")
+  .description("Run diagnostic checks on your Paperclip setup")
+  .option("-c, --config <path>", "Path to config file")
+  .option("--repair", "Attempt to repair issues automatically")
+  .alias("--fix")
+  .option("-y, --yes", "Skip repair confirmation prompts")
+  .action(doctor);
+
+program
+  .command("configure")
+  .description("Update configuration sections")
+  .option("-c, --config <path>", "Path to config file")
+  .option("-s, --section <section>", "Section to configure (llm, database, logging, server)")
+  .action(configure);
+
+program.parse();

cli/src/prompts/database.ts

@@ -0,0 +1,48 @@
+import * as p from "@clack/prompts";
+import type { DatabaseConfig } from "../config/schema.js";
+
+export async function promptDatabase(): Promise<DatabaseConfig> {
+  const mode = await p.select({
+    message: "Database mode",
+    options: [
+      { value: "pglite" as const, label: "PGlite (embedded, no setup needed)", hint: "recommended" },
+      { value: "postgres" as const, label: "PostgreSQL (external server)" },
+    ],
+  });
+
+  if (p.isCancel(mode)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  if (mode === "postgres") {
+    const connectionString = await p.text({
+      message: "PostgreSQL connection string",
+      placeholder: "postgres://user:pass@localhost:5432/paperclip",
+      validate: (val) => {
+        if (!val) return "Connection string is required for PostgreSQL mode";
+        if (!val.startsWith("postgres")) return "Must be a postgres:// or postgresql:// URL";
+      },
+    });
+
+    if (p.isCancel(connectionString)) {
+      p.cancel("Setup cancelled.");
+      process.exit(0);
+    }
+
+    return { mode: "postgres", connectionString, pgliteDataDir: "./data/pglite" };
+  }
+
+  const pgliteDataDir = await p.text({
+    message: "PGlite data directory",
+    defaultValue: "./data/pglite",
+    placeholder: "./data/pglite",
+  });
+
+  if (p.isCancel(pgliteDataDir)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  return { mode: "pglite", pgliteDataDir: pgliteDataDir || "./data/pglite" };
+}

cli/src/prompts/llm.ts

@@ -0,0 +1,43 @@
+import * as p from "@clack/prompts";
+import type { LlmConfig } from "../config/schema.js";
+
+export async function promptLlm(): Promise<LlmConfig | undefined> {
+  const configureLlm = await p.confirm({
+    message: "Configure an LLM provider now?",
+    initialValue: false,
+  });
+
+  if (p.isCancel(configureLlm)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  if (!configureLlm) return undefined;
+
+  const provider = await p.select({
+    message: "LLM provider",
+    options: [
+      { value: "claude" as const, label: "Claude (Anthropic)" },
+      { value: "openai" as const, label: "OpenAI" },
+    ],
+  });
+
+  if (p.isCancel(provider)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  const apiKey = await p.password({
+    message: `${provider === "claude" ? "Anthropic" : "OpenAI"} API key`,
+    validate: (val) => {
+      if (!val) return "API key is required";
+    },
+  });
+
+  if (p.isCancel(apiKey)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  return { provider, apiKey };
+}

cli/src/prompts/logging.ts

@@ -0,0 +1,35 @@
+import * as p from "@clack/prompts";
+import type { LoggingConfig } from "../config/schema.js";
+
+export async function promptLogging(): Promise<LoggingConfig> {
+  const mode = await p.select({
+    message: "Logging mode",
+    options: [
+      { value: "file" as const, label: "File-based logging", hint: "recommended" },
+      { value: "cloud" as const, label: "Cloud logging", hint: "coming soon" },
+    ],
+  });
+
+  if (p.isCancel(mode)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  if (mode === "file") {
+    const logDir = await p.text({
+      message: "Log directory",
+      defaultValue: "./data/logs",
+      placeholder: "./data/logs",
+    });
+
+    if (p.isCancel(logDir)) {
+      p.cancel("Setup cancelled.");
+      process.exit(0);
+    }
+
+    return { mode: "file", logDir: logDir || "./data/logs" };
+  }
+
+  p.note("Cloud logging is coming soon. Using file-based logging for now.");
+  return { mode: "file", logDir: "./data/logs" };
+}

cli/src/prompts/server.ts

@@ -0,0 +1,35 @@
+import * as p from "@clack/prompts";
+import type { ServerConfig } from "../config/schema.js";
+
+export async function promptServer(): Promise<ServerConfig> {
+  const portStr = await p.text({
+    message: "Server port",
+    defaultValue: "3100",
+    placeholder: "3100",
+    validate: (val) => {
+      const n = Number(val);
+      if (isNaN(n) || n < 1 || n > 65535 || !Number.isInteger(n)) {
+        return "Must be an integer between 1 and 65535";
+      }
+    },
+  });
+
+  if (p.isCancel(portStr)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  const port = Number(portStr) || 3100;
+
+  const serveUi = await p.confirm({
+    message: "Serve the UI from the server?",
+    initialValue: false,
+  });
+
+  if (p.isCancel(serveUi)) {
+    p.cancel("Setup cancelled.");
+    process.exit(0);
+  }
+
+  return { port, serveUi };
+}

cli/src/utils/net.ts

@@ -0,0 +1,18 @@
+import net from "node:net";
+
+export function checkPort(port: number): Promise<{ available: boolean; error?: string }> {
+  return new Promise((resolve) => {
+    const server = net.createServer();
+    server.once("error", (err: NodeJS.ErrnoException) => {
+      if (err.code === "EADDRINUSE") {
+        resolve({ available: false, error: `Port ${port} is already in use` });
+      } else {
+        resolve({ available: false, error: err.message });
+      }
+    });
+    server.once("listening", () => {
+      server.close(() => resolve({ available: true }));
+    });
+    server.listen(port, "127.0.0.1");
+  });
+}