diff --git a/docs/gateway/configuration.md b/docs/gateway/configuration.md
index 032015e37..48236e88d 100644
--- a/docs/gateway/configuration.md
+++ b/docs/gateway/configuration.md
@@ -1194,6 +1194,12 @@ Control UI base path:
 - Examples: `"/ui"`, `"/clawdbot"`, `"/apps/clawdbot"`.
 - Default: root (`/`) (unchanged).
 
+Related docs:
+- [Control UI](/web/control-ui)
+- [Web overview](/web)
+- [Tailscale](/gateway/tailscale)
+- [Remote access](/gateway/remote)
+
 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).
diff --git a/src/commands/configure.ts b/src/commands/configure.ts
index 027f35dd0..60a56516f 100644
--- a/src/commands/configure.ts
+++ b/src/commands/configure.ts
@@ -150,6 +150,14 @@ async function promptGatewayConfig(
 
   let tailscaleResetOnExit = false;
   if (tailscaleMode !== "off") {
+    note(
+      [
+        "Docs:",
+        "https://docs.clawd.bot/gateway/tailscale",
+        "https://docs.clawd.bot/web",
+      ].join("\n"),
+      "Tailscale",
+    );
     tailscaleResetOnExit = Boolean(
       guardCancel(
         await confirm({
@@ -300,6 +308,7 @@ async function promptAuthConfig(
     } catch (err) {
       spin.stop("OAuth failed");
       runtime.error(String(err));
+      note("Trouble with OAuth? See https://docs.clawd.bot/start/faq", "OAuth");
     }
   } else if (authChoice === "openai-codex") {
     const isRemote = isRemoteEnvironment();
@@ -373,6 +382,7 @@ async function promptAuthConfig(
     } catch (err) {
       spin.stop("OpenAI OAuth failed");
       runtime.error(String(err));
+      note("Trouble with OAuth? See https://docs.clawd.bot/start/faq", "OAuth");
     }
   } else if (authChoice === "antigravity") {
     const isRemote = isRemoteEnvironment();
@@ -447,6 +457,7 @@ async function promptAuthConfig(
     } catch (err) {
       spin.stop("Antigravity OAuth failed");
       runtime.error(String(err));
+      note("Trouble with OAuth? See https://docs.clawd.bot/start/faq", "OAuth");
     }
   } else if (authChoice === "apiKey") {
     const key = guardCancel(
@@ -608,9 +619,11 @@ export async function runConfigureWizard(
     note(summarizeExistingConfig(baseConfig), title);
     if (!snapshot.valid && snapshot.issues.length > 0) {
       note(
-        snapshot.issues
-          .map((iss) => `- ${iss.path}: ${iss.message}`)
-          .join("\n"),
+        [
+          ...snapshot.issues.map((iss) => `- ${iss.path}: ${iss.message}`),
+          "",
+          "Docs: https://docs.clawd.bot/gateway/configuration",
+        ].join("\n"),
         "Config issues",
       );
     }
@@ -789,6 +802,14 @@ export async function runConfigureWizard(
       await healthCommand({ json: false, timeoutMs: 10_000 }, runtime);
     } catch (err) {
       runtime.error(`Health check failed: ${String(err)}`);
+      note(
+        [
+          "Docs:",
+          "https://docs.clawd.bot/gateway/health",
+          "https://docs.clawd.bot/gateway/troubleshooting",
+        ].join("\n"),
+        "Health check help",
+      );
     }
   }
 
@@ -797,20 +818,22 @@ export async function runConfigureWizard(
     runtime.error(controlUiAssets.message);
   }
 
-  note(
-    (() => {
-      const bind = nextConfig.gateway?.bind ?? "loopback";
-      const links = resolveControlUiLinks({
-        bind,
-        port: gatewayPort,
-        basePath: nextConfig.gateway?.controlUi?.basePath,
-      });
-      return [`Web UI: ${links.httpUrl}`, `Gateway WS: ${links.wsUrl}`].join(
-        "\n",
-      );
-    })(),
-    "Control UI",
-  );
+    note(
+      (() => {
+        const bind = nextConfig.gateway?.bind ?? "loopback";
+        const links = resolveControlUiLinks({
+          bind,
+          port: gatewayPort,
+          basePath: nextConfig.gateway?.controlUi?.basePath,
+        });
+        return [
+          `Web UI: ${links.httpUrl}`,
+          `Gateway WS: ${links.wsUrl}`,
+          "Docs: https://docs.clawd.bot/web/control-ui",
+        ].join("\n");
+      })(),
+      "Control UI",
+    );
 
   const browserSupport = await detectBrowserOpenSupport();
   if (!browserSupport.ok) {
diff --git a/src/commands/onboard-helpers.ts b/src/commands/onboard-helpers.ts
index 43e91e33d..3cd1a48d7 100644
--- a/src/commands/onboard-helpers.ts
+++ b/src/commands/onboard-helpers.ts
@@ -195,6 +195,9 @@ export function formatControlUiSshHint(params: {
     "Then open:",
     localUrl,
     authedUrl,
+    "Docs:",
+    "https://docs.clawd.bot/gateway/remote",
+    "https://docs.clawd.bot/web/control-ui",
   ]
     .filter(Boolean)
     .join("\n");
diff --git a/src/commands/onboard-providers.ts b/src/commands/onboard-providers.ts
index 4ac6f032f..d061affd6 100644
--- a/src/commands/onboard-providers.ts
+++ b/src/commands/onboard-providers.ts
@@ -39,6 +39,7 @@ async function noteProviderPrimer(prompter: WizardPrompter): Promise<void> {
       "DM security: default is pairing; unknown DMs get a pairing code.",
       "Approve with: clawdbot pairing approve --provider <provider> <code>",
       'Public DMs require dmPolicy="open" + allowFrom=["*"].',
+      "Docs: https://docs.clawd.bot/start/pairing",
       "",
       "WhatsApp: links via WhatsApp Web (scan QR), stores creds for future sends.",
       "WhatsApp: dedicated second number recommended; primary number OK (self-chat).",
@@ -59,6 +60,7 @@ async function noteTelegramTokenHelp(prompter: WizardPrompter): Promise<void> {
       "2) Run /newbot (or /mybots)",
       "3) Copy the token (looks like 123456:ABC...)",
       "Tip: you can also set TELEGRAM_BOT_TOKEN in your env.",
+      "Docs: https://docs.clawd.bot/telegram",
     ].join("\n"),
     "Telegram bot token",
   );
@@ -71,6 +73,7 @@ async function noteDiscordTokenHelp(prompter: WizardPrompter): Promise<void> {
       "2) Bot → Add Bot → Reset Token → copy token",
       "3) OAuth2 → URL Generator → scope 'bot' → invite to your server",
       "Tip: enable Message Content Intent if you need message text.",
+      "Docs: https://docs.clawd.bot/discord",
     ].join("\n"),
     "Discord bot token",
   );
@@ -158,6 +161,7 @@ async function noteSlackTokenHelp(
       "4) Enable Event Subscriptions (socket) for message events",
       "5) App Home → enable the Messages tab for DMs",
       "Tip: set SLACK_BOT_TOKEN + SLACK_APP_TOKEN in your env.",
+      "Docs: https://docs.clawd.bot/slack",
       "",
       "Manifest (JSON):",
       manifest,
@@ -298,6 +302,7 @@ async function maybeConfigureDmPolicies(params: {
         "Default: pairing (unknown DMs get a pairing code).",
         `Approve: clawdbot pairing approve --provider ${params.provider} <code>`,
         `Public DMs: ${params.policyKey}="open" + ${params.allowFromKey} includes "*".`,
+        "Docs: https://docs.clawd.bot/start/pairing",
       ].join("\n"),
       `${params.label} DM access`,
     );
@@ -383,6 +388,7 @@ async function promptWhatsAppAllowFrom(
       "- disabled: ignore WhatsApp DMs",
       "",
       `Current: dmPolicy=${existingPolicy}, allowFrom=${existingLabel}`,
+      "Docs: https://docs.clawd.bot/whatsapp",
     ].join("\n"),
     "WhatsApp DM access",
   );
@@ -551,6 +557,7 @@ export async function setupProviders(
         [
           "Scan the QR with WhatsApp on your phone.",
           `Credentials are stored under ${WA_WEB_AUTH_DIR}/ for future runs.`,
+          "Docs: https://docs.clawd.bot/whatsapp",
         ].join("\n"),
         "WhatsApp linking",
       );
@@ -566,6 +573,10 @@ export async function setupProviders(
         await loginWeb(false, "web");
       } catch (err) {
         runtime.error(`WhatsApp login failed: ${String(err)}`);
+        await prompter.note(
+          "Docs: https://docs.clawd.bot/whatsapp",
+          "WhatsApp help",
+        );
       }
     } else if (!whatsappLinked) {
       await prompter.note(
@@ -864,6 +875,7 @@ export async function setupProviders(
         'Link device with: signal-cli link -n "Clawdbot"',
         "Scan QR in Signal → Linked Devices",
         "Then run: clawdbot gateway call providers.status --params '{\"probe\":true}'",
+        "Docs: https://docs.clawd.bot/signal",
       ].join("\n"),
       "Signal next steps",
     );
@@ -902,6 +914,7 @@ export async function setupProviders(
         "Ensure Clawdbot has Full Disk Access to Messages DB.",
         "Grant Automation permission for Messages when prompted.",
         "List chats with: imsg chats --limit 20",
+        "Docs: https://docs.clawd.bot/imessage",
       ].join("\n"),
       "iMessage next steps",
     );
diff --git a/src/commands/onboard-remote.ts b/src/commands/onboard-remote.ts
index e08b73230..61d62b54d 100644
--- a/src/commands/onboard-remote.ts
+++ b/src/commands/onboard-remote.ts
@@ -42,7 +42,10 @@ export async function promptRemoteGatewayConfig(
 
   if (!hasBonjourTool) {
     await prompter.note(
-      "Bonjour discovery requires dns-sd (macOS) or avahi-browse (Linux).",
+      [
+        "Bonjour discovery requires dns-sd (macOS) or avahi-browse (Linux).",
+        "Docs: https://docs.clawd.bot/gateway/discovery",
+      ].join("\n"),
       "Discovery",
     );
   }
@@ -98,6 +101,7 @@ export async function promptRemoteGatewayConfig(
             `ssh -N -L 18789:127.0.0.1:18789 <user>@${host}${
               selectedBeacon.sshPort ? ` -p ${selectedBeacon.sshPort}` : ""
             }`,
+            "Docs: https://docs.clawd.bot/gateway/remote",
           ].join("\n"),
           "SSH tunnel",
         );
diff --git a/src/commands/onboard-skills.ts b/src/commands/onboard-skills.ts
index 207480379..abab220cf 100644
--- a/src/commands/onboard-skills.ts
+++ b/src/commands/onboard-skills.ts
@@ -168,6 +168,7 @@ export async function setupSkills(
         runtime.log(
           "Tip: run `clawdbot doctor` to review skills + requirements.",
         );
+        runtime.log("Docs: https://docs.clawd.bot/skills");
       }
     }
   }
diff --git a/src/wizard/onboarding.ts b/src/wizard/onboarding.ts
index beb405b68..6b8842a8a 100644
--- a/src/wizard/onboarding.ts
+++ b/src/wizard/onboarding.ts
@@ -142,9 +142,11 @@ export async function runOnboardingWizard(
     await prompter.note(summarizeExistingConfig(baseConfig), title);
     if (!snapshot.valid && snapshot.issues.length > 0) {
       await prompter.note(
-        snapshot.issues
-          .map((iss) => `- ${iss.path}: ${iss.message}`)
-          .join("\n"),
+        [
+          ...snapshot.issues.map((iss) => `- ${iss.path}: ${iss.message}`),
+          "",
+          "Docs: https://docs.clawd.bot/gateway/configuration",
+        ].join("\n"),
         "Config issues",
       );
     }
@@ -302,6 +304,10 @@ export async function runOnboardingWizard(
     } catch (err) {
       spin.stop("OAuth failed");
       runtime.error(String(err));
+      await prompter.note(
+        "Trouble with OAuth? See https://docs.clawd.bot/start/faq",
+        "OAuth help",
+      );
     }
   } else if (authChoice === "openai-codex") {
     const isRemote = isRemoteEnvironment();
@@ -375,6 +381,10 @@ export async function runOnboardingWizard(
     } catch (err) {
       spin.stop("OpenAI OAuth failed");
       runtime.error(String(err));
+      await prompter.note(
+        "Trouble with OAuth? See https://docs.clawd.bot/start/faq",
+        "OAuth help",
+      );
     }
   } else if (authChoice === "antigravity") {
     const isRemote = isRemoteEnvironment();
@@ -448,6 +458,10 @@ export async function runOnboardingWizard(
     } catch (err) {
       spin.stop("Antigravity OAuth failed");
       runtime.error(String(err));
+      await prompter.note(
+        "Trouble with OAuth? See https://docs.clawd.bot/start/faq",
+        "OAuth help",
+      );
     }
   } else if (authChoice === "apiKey") {
     const key = await prompter.text({
@@ -520,6 +534,14 @@ export async function runOnboardingWizard(
 
   let tailscaleResetOnExit = false;
   if (tailscaleMode !== "off") {
+    await prompter.note(
+      [
+        "Docs:",
+        "https://docs.clawd.bot/gateway/tailscale",
+        "https://docs.clawd.bot/web",
+      ].join("\n"),
+      "Tailscale",
+    );
     tailscaleResetOnExit = Boolean(
       await prompter.confirm({
         message: "Reset Tailscale serve/funnel on exit?",
@@ -693,6 +715,14 @@ export async function runOnboardingWizard(
     await healthCommand({ json: false, timeoutMs: 10_000 }, runtime);
   } catch (err) {
     runtime.error(`Health check failed: ${String(err)}`);
+    await prompter.note(
+      [
+        "Docs:",
+        "https://docs.clawd.bot/gateway/health",
+        "https://docs.clawd.bot/gateway/troubleshooting",
+      ].join("\n"),
+      "Health check help",
+    );
   }
 
   const controlUiAssets = await ensureControlUiAssetsBuilt(runtime);
@@ -726,6 +756,7 @@ export async function runOnboardingWizard(
         `Web UI: ${links.httpUrl}`,
         tokenParam ? `Web UI (with token): ${authedUrl}` : undefined,
         `Gateway WS: ${links.wsUrl}`,
+        "Docs: https://docs.clawd.bot/web/control-ui",
       ]
         .filter(Boolean)
         .join("\n");
@@ -772,5 +803,13 @@ export async function runOnboardingWizard(
     }
   }
 
+  await prompter.note(
+    [
+      "Back up your agent workspace.",
+      "Docs: https://docs.clawd.bot/concepts/agent-workspace",
+    ].join("\n"),
+    "Workspace backup",
+  );
+
   await prompter.outro("Onboarding complete.");
 }