diff --git a/src/cli/setup/automation.ts b/src/cli/setup/automation.ts
index 3c58db4..80293c5 100644
--- a/src/cli/setup/automation.ts
+++ b/src/cli/setup/automation.ts
@@ -5,18 +5,27 @@ export async function setupAutomation(p: Prompter, builder: ConfigBuilder): Prom
   const cron = await p.confirm('Enable cron scheduler?', false);
   if (cron) {
     builder.setCronEnabled();
-    p.println('✓ Cron enabled — add jobs to config.yaml later');
+    p.println('✓ Cron enabled — add jobs to config.yaml under automation.cron.jobs[]');
   }
 
   const webhooks = await p.confirm('Enable webhook receiver?', false);
   if (webhooks) {
+    p.println('  Webhooks accept HTTP POST at /webhooks/:name on the gateway port.');
+    p.println('  Set a shared secret to verify requests via HMAC signature.');
     const secret = await p.ask('Webhook shared secret (optional)', '');
     builder.setWebhooksEnabled(secret || undefined);
-    p.println('✓ Webhooks enabled');
+    p.println('✓ Webhooks enabled — define triggers in config.yaml under automation.webhooks[]');
   }
 
   const gmail = await p.confirm('Enable Gmail watcher?', false);
   if (gmail) {
+    p.println('  To set up Gmail access:');
+    p.println('  1. Go to https://console.cloud.google.com → create or select a project');
+    p.println('  2. Enable the Gmail API and Cloud Pub/Sub API');
+    p.println('  3. Go to APIs & Services → Credentials → Create Credentials → OAuth client ID');
+    p.println('  4. Choose "Desktop app", download the JSON file');
+    p.println('  5. Save it as ~/.config/flynn/gmail-credentials.json');
+    p.println('  On first run, Flynn will open a browser for OAuth consent and save the token.');
     const creds = await p.ask('OAuth credentials file', '~/.config/flynn/gmail-credentials.json');
     builder.setGmailEnabled(creds, 'webchat', 'gmail');
     p.println('✓ Gmail watcher enabled');
diff --git a/src/cli/setup/channels.ts b/src/cli/setup/channels.ts
index 58d79c5..f2d3005 100644
--- a/src/cli/setup/channels.ts
+++ b/src/cli/setup/channels.ts
@@ -2,6 +2,9 @@ import type { Prompter } from './prompts.js';
 import type { ConfigBuilder } from './config.js';
 
 async function setupTelegram(p: Prompter, builder: ConfigBuilder): Promise<void> {
+  p.println('  1. Message @BotFather on Telegram and use /newbot to create a bot');
+  p.println('  2. Copy the bot token it gives you');
+  p.println('  3. To find your chat ID, message @userinfobot or @RawDataBot');
   const botToken = await p.password('Bot token (from @BotFather)');
   const chatIdsRaw = await p.ask('Allowed chat IDs (comma-separated)');
   const chatIds = chatIdsRaw.split(',').map(s => parseInt(s.trim(), 10)).filter(n => !isNaN(n));
@@ -14,6 +17,11 @@ async function setupTelegram(p: Prompter, builder: ConfigBuilder): Promise<void>
 }
 
 async function setupDiscord(p: Prompter, builder: ConfigBuilder): Promise<void> {
+  p.println('  1. Go to https://discord.com/developers/applications');
+  p.println('  2. Create an application → Bot → copy the bot token');
+  p.println('  3. Enable MESSAGE CONTENT intent under Bot settings');
+  p.println('  4. Invite bot to your server with OAuth2 URL Generator (bot scope + Send Messages)');
+  p.println('  5. Guild ID: right-click your server → Copy Server ID (enable Developer Mode in settings)');
   const botToken = await p.password('Bot token');
   const guildIdsRaw = await p.ask('Allowed guild IDs (comma-separated, or * for all)');
   const guildIds = guildIdsRaw === '*' ? [] : guildIdsRaw.split(',').map(s => s.trim()).filter(Boolean);
@@ -22,6 +30,11 @@ async function setupDiscord(p: Prompter, builder: ConfigBuilder): Promise<void>
 }
 
 async function setupSlack(p: Prompter, builder: ConfigBuilder): Promise<void> {
+  p.println('  1. Go to https://api.slack.com/apps and create a new app');
+  p.println('  2. Enable Socket Mode → generate an App Token (xapp-...)');
+  p.println('  3. Under OAuth & Permissions, install to workspace → copy Bot Token (xoxb-...)');
+  p.println('  4. Under Basic Information → copy Signing Secret');
+  p.println('  5. Channel IDs: right-click a channel → View channel details → copy the ID at bottom');
   const botToken = await p.password('Bot token (xoxb-...)');
   const appToken = await p.password('App token (xapp-...)');
   const signingSecret = await p.password('Signing secret');
diff --git a/src/cli/setup/gateway.ts b/src/cli/setup/gateway.ts
index 7a99184..8c670f5 100644
--- a/src/cli/setup/gateway.ts
+++ b/src/cli/setup/gateway.ts
@@ -2,9 +2,12 @@ import type { Prompter } from './prompts.js';
 import type { ConfigBuilder } from './config.js';
 
 export async function setupGateway(p: Prompter, builder: ConfigBuilder): Promise<void> {
+  p.println('  The gateway serves the web dashboard and WebSocket API.');
   const port = await p.ask('Gateway port', '18800');
   builder.setGatewayPort(parseInt(port, 10) || 18800);
 
+  p.println();
+  p.println('  An auth token protects gateway access (required for remote/Tailscale use).');
   const wantAuth = await p.confirm('Set auth token?', false);
   if (wantAuth) {
     const token = await p.password('Auth token');
@@ -12,12 +15,16 @@ export async function setupGateway(p: Prompter, builder: ConfigBuilder): Promise
     p.println('✓ Gateway auth token set');
   }
 
+  p.println();
+  p.println('  Tailscale Serve exposes the gateway on your tailnet (requires tailscale CLI).');
   const tailscale = await p.confirm('Enable Tailscale Serve?', false);
   if (tailscale) {
     builder.setTailscaleServe(true);
     p.println('✓ Tailscale Serve enabled');
   }
 
+  p.println();
+  p.println('  Gateway lock limits connections to one client at a time.');
   const lock = await p.confirm('Enable gateway lock (single client)?', false);
   if (lock) {
     builder.setGatewayLock(true);
diff --git a/src/cli/setup/memory.ts b/src/cli/setup/memory.ts
index 3e5860c..83c577b 100644
--- a/src/cli/setup/memory.ts
+++ b/src/cli/setup/memory.ts
@@ -11,9 +11,13 @@ const EMBEDDING_PROVIDERS = [
 const REUSABLE_PROVIDERS = ['openai', 'gemini'];
 
 export async function setupMemory(p: Prompter, builder: ConfigBuilder): Promise<void> {
+  p.println('  Vector search enables semantic memory — Flynn remembers and retrieves');
+  p.println('  information based on meaning, not just keywords.');
   const enable = await p.confirm('Enable vector search for semantic memory?', false);
   if (!enable) return;
 
+  p.println('  Pick a provider to generate embeddings (vector representations of text).');
+  p.println('  If you already configured OpenAI or Gemini as a model, you can reuse that key.');
   const provider = await p.choose('Embedding provider:', EMBEDDING_PROVIDERS);
 
   const config = builder.build();
diff --git a/src/cli/setup/providers.ts b/src/cli/setup/providers.ts
index 5fc0801..75441fd 100644
--- a/src/cli/setup/providers.ts
+++ b/src/cli/setup/providers.ts
@@ -26,9 +26,23 @@ const SECOND_TIER: ProviderDef[] = [
   { name: 'GitHub Models', provider: 'github', defaultModel: 'claude-sonnet-4-20250514', needsApiKey: false, needsEndpoint: false },
 ];
 
+const PROVIDER_HELP: Record<string, string> = {
+  anthropic: 'Get your API key at https://console.anthropic.com/settings/keys',
+  openai: 'Get your API key at https://platform.openai.com/api-keys',
+  ollama: 'Ollama runs locally — install from https://ollama.com and run: ollama serve',
+  gemini: 'Get your API key at https://aistudio.google.com/apikey',
+  openrouter: 'Get your API key at https://openrouter.ai/keys (supports 200+ models)',
+  xai: 'Get your API key at https://console.x.ai',
+  bedrock: 'Uses AWS credentials from environment (~/.aws/credentials or IAM role)',
+  github: 'Uses GitHub Copilot — authenticate via OAuth device flow on first use',
+};
+
 async function configureProvider(p: Prompter, def: ProviderDef): Promise<{
   provider: string; model: string; api_key?: string; endpoint?: string;
 }> {
+  const help = PROVIDER_HELP[def.provider];
+  if (help) p.println(`  ${help}`);
+
   const config: Record<string, string> = { provider: def.provider };
   if (def.needsApiKey) config.api_key = await p.password(def.apiKeyLabel ?? 'API key');
   if (def.needsEndpoint) config.endpoint = await p.ask('Host', def.defaultEndpoint);
diff --git a/src/cli/setup/security.ts b/src/cli/setup/security.ts
index 5cb9623..3db82cf 100644
--- a/src/cli/setup/security.ts
+++ b/src/cli/setup/security.ts
@@ -9,18 +9,29 @@ const TOOL_PROFILES = [
 ];
 
 export async function setupSecurity(p: Prompter, builder: ConfigBuilder): Promise<void> {
+  p.println('  Docker sandboxing runs tool commands in isolated containers.');
+  p.println('  Requires Docker installed and running.');
   const sandbox = await p.confirm('Enable Docker sandboxing?', false);
   if (sandbox) {
     builder.setSandboxEnabled(true);
     p.println('✓ Docker sandboxing enabled');
   }
 
+  p.println();
+  p.println('  DM pairing requires unknown senders to enter a code before chatting.');
+  p.println('  Generate codes via the gateway or TUI /pair command.');
   const pairing = await p.confirm('Enable DM pairing for unknown senders?', false);
   if (pairing) {
     builder.setPairingEnabled(true);
     p.println('✓ DM pairing enabled');
   }
 
+  p.println();
+  p.println('  Tool profiles control which tools the agent can use:');
+  p.println('    full        — all tools available (file, shell, web, memory, messaging)');
+  p.println('    coding      — file system + shell + sessions + memory (no messaging/web)');
+  p.println('    messaging   — send messages only (no file/shell access)');
+  p.println('    minimal     — status checks only (read-only, safest)');
   const profile = await p.choose('Tool policy profile:', TOOL_PROFILES);
   builder.setToolProfile(profile);
 }