diff --git a/src/commands/configure.daemon.ts b/src/commands/configure.daemon.ts
index c05a60d30..a06e533c6 100644
--- a/src/commands/configure.daemon.ts
+++ b/src/commands/configure.daemon.ts
@@ -8,6 +8,7 @@ import {
 } from "../daemon/runtime-paths.js";
 import { resolveGatewayService } from "../daemon/service.js";
 import { buildServiceEnvironment } from "../daemon/service-env.js";
+import { withProgress } from "../cli/progress.js";
 import type { RuntimeEnv } from "../runtime.js";
 import { note } from "../terminal/note.js";
 import { confirm, select } from "./configure.shared.js";
@@ -43,63 +44,89 @@ export async function maybeInstallDaemon(params: {
       params.runtime,
     );
     if (action === "restart") {
-      await service.restart({
-        profile: process.env.CLAWDBOT_PROFILE,
-        stdout: process.stdout,
-      });
+      await withProgress(
+        { label: "Gateway daemon", indeterminate: true, delayMs: 0 },
+        async (progress) => {
+          progress.setLabel("Restarting Gateway daemon…");
+          await service.restart({
+            profile: process.env.CLAWDBOT_PROFILE,
+            stdout: process.stdout,
+          });
+          progress.setLabel("Gateway daemon restarted.");
+        },
+      );
       shouldCheckLinger = true;
       shouldInstall = false;
     }
     if (action === "skip") return;
     if (action === "reinstall") {
-      await service.uninstall({ env: process.env, stdout: process.stdout });
+      await withProgress(
+        { label: "Gateway daemon", indeterminate: true, delayMs: 0 },
+        async (progress) => {
+          progress.setLabel("Uninstalling Gateway daemon…");
+          await service.uninstall({ env: process.env, stdout: process.stdout });
+          progress.setLabel("Gateway daemon uninstalled.");
+        },
+      );
     }
   }
 
   if (shouldInstall) {
-    if (!params.daemonRuntime) {
-      daemonRuntime = guardCancel(
-        await select({
-          message: "Gateway daemon runtime",
-          options: GATEWAY_DAEMON_RUNTIME_OPTIONS,
-          initialValue: DEFAULT_GATEWAY_DAEMON_RUNTIME,
-        }),
-        params.runtime,
-      ) as GatewayDaemonRuntime;
-    }
-    const devMode =
-      process.argv[1]?.includes(`${path.sep}src${path.sep}`) && process.argv[1]?.endsWith(".ts");
-    const nodePath = await resolvePreferredNodePath({
-      env: process.env,
-      runtime: daemonRuntime,
-    });
-    const { programArguments, workingDirectory } = await resolveGatewayProgramArguments({
-      port: params.port,
-      dev: devMode,
-      runtime: daemonRuntime,
-      nodePath,
-    });
-    if (daemonRuntime === "node") {
-      const systemNode = await resolveSystemNodeInfo({ env: process.env });
-      const warning = renderSystemNodeWarning(systemNode, programArguments[0]);
-      if (warning) note(warning, "Gateway runtime");
-    }
-    const environment = buildServiceEnvironment({
-      env: process.env,
-      port: params.port,
-      token: params.gatewayToken,
-      launchdLabel:
-        process.platform === "darwin"
-          ? resolveGatewayLaunchAgentLabel(process.env.CLAWDBOT_PROFILE)
-          : undefined,
-    });
-    await service.install({
-      env: process.env,
-      stdout: process.stdout,
-      programArguments,
-      workingDirectory,
-      environment,
-    });
+    await withProgress(
+      { label: "Gateway daemon", indeterminate: true, delayMs: 0 },
+      async (progress) => {
+        if (!params.daemonRuntime) {
+          daemonRuntime = guardCancel(
+            await select({
+              message: "Gateway daemon runtime",
+              options: GATEWAY_DAEMON_RUNTIME_OPTIONS,
+              initialValue: DEFAULT_GATEWAY_DAEMON_RUNTIME,
+            }),
+            params.runtime,
+          ) as GatewayDaemonRuntime;
+        }
+
+        progress.setLabel("Preparing Gateway daemon…");
+
+        const devMode =
+          process.argv[1]?.includes(`${path.sep}src${path.sep}`) &&
+          process.argv[1]?.endsWith(".ts");
+        const nodePath = await resolvePreferredNodePath({
+          env: process.env,
+          runtime: daemonRuntime,
+        });
+        const { programArguments, workingDirectory } = await resolveGatewayProgramArguments({
+          port: params.port,
+          dev: devMode,
+          runtime: daemonRuntime,
+          nodePath,
+        });
+        if (daemonRuntime === "node") {
+          const systemNode = await resolveSystemNodeInfo({ env: process.env });
+          const warning = renderSystemNodeWarning(systemNode, programArguments[0]);
+          if (warning) note(warning, "Gateway runtime");
+        }
+        const environment = buildServiceEnvironment({
+          env: process.env,
+          port: params.port,
+          token: params.gatewayToken,
+          launchdLabel:
+            process.platform === "darwin"
+              ? resolveGatewayLaunchAgentLabel(process.env.CLAWDBOT_PROFILE)
+              : undefined,
+        });
+
+        progress.setLabel("Installing Gateway daemon…");
+        await service.install({
+          env: process.env,
+          stdout: process.stdout,
+          programArguments,
+          workingDirectory,
+          environment,
+        });
+        progress.setLabel("Gateway daemon installed.");
+      },
+    );
     shouldCheckLinger = true;
   }
 
diff --git a/src/commands/configure.wizard.ts b/src/commands/configure.wizard.ts
index 2a38ba691..c09a6d8a8 100644
--- a/src/commands/configure.wizard.ts
+++ b/src/commands/configure.wizard.ts
@@ -98,9 +98,18 @@ async function promptWebToolsConfig(
   const existingFetch = nextConfig.tools?.web?.fetch;
   const hasSearchKey = Boolean(existingSearch?.apiKey);
 
+  note(
+    [
+      "Web search lets your agent look things up online using the `web_search` tool.",
+      "It requires a Brave Search API key (you can store it in the config or set BRAVE_API_KEY in the Gateway environment).",
+      "Docs: https://docs.clawd.bot/tools/web",
+    ].join("\n"),
+    "Web search",
+  );
+
   const enableSearch = guardCancel(
     await confirm({
-      message: "Enable web_search (Brave Search API)?",
+      message: "Enable web_search (Brave Search)?",
       initialValue: existingSearch?.enabled ?? hasSearchKey,
     }),
     runtime,
@@ -116,7 +125,7 @@ async function promptWebToolsConfig(
       await text({
         message: hasSearchKey
           ? "Brave Search API key (leave blank to keep current or use BRAVE_API_KEY)"
-          : "Brave Search API key (leave blank to use BRAVE_API_KEY)",
+          : "Brave Search API key (paste it here; leave blank to use BRAVE_API_KEY)",
         placeholder: hasSearchKey ? "Leave blank to keep current" : "BSA...",
       }),
       runtime,
@@ -127,7 +136,8 @@ async function promptWebToolsConfig(
     } else if (!hasSearchKey) {
       note(
         [
-          "No key stored. web_search needs BRAVE_API_KEY or tools.web.search.apiKey.",
+          "No key stored yet, so web_search will stay unavailable.",
+          "Store a key here or set BRAVE_API_KEY in the Gateway environment.",
           "Docs: https://docs.clawd.bot/tools/web",
         ].join("\n"),
         "Web search",
diff --git a/src/wizard/onboarding.finalize.ts b/src/wizard/onboarding.finalize.ts
index 62671ca54..29b91239d 100644
--- a/src/wizard/onboarding.finalize.ts
+++ b/src/wizard/onboarding.finalize.ts
@@ -49,6 +49,19 @@ type FinalizeOnboardingOptions = {
 export async function finalizeOnboardingWizard(options: FinalizeOnboardingOptions) {
   const { flow, opts, baseConfig, nextConfig, settings, prompter, runtime } = options;
 
+  const withWizardProgress = async <T>(
+    label: string,
+    options: { doneMessage?: string },
+    work: (progress: { update: (message: string) => void }) => Promise<T>,
+  ): Promise<T> => {
+    const progress = prompter.progress(label);
+    try {
+      return await work(progress);
+    } finally {
+      progress.stop(options.doneMessage);
+    }
+  };
+
   const systemdAvailable =
     process.platform === "linux" ? await isSystemdUserServiceAvailable() : true;
   if (process.platform === "linux" && !systemdAvailable) {
@@ -123,12 +136,26 @@ export async function finalizeOnboardingWizard(options: FinalizeOnboardingOption
         ],
       })) as "restart" | "reinstall" | "skip";
       if (action === "restart") {
-        await service.restart({
-          profile: process.env.CLAWDBOT_PROFILE,
-          stdout: process.stdout,
-        });
+        await withWizardProgress(
+          "Gateway daemon",
+          { doneMessage: "Gateway daemon restarted." },
+          async (progress) => {
+          progress.update("Restarting Gateway daemon…");
+          await service.restart({
+            profile: process.env.CLAWDBOT_PROFILE,
+            stdout: process.stdout,
+          });
+          },
+        );
       } else if (action === "reinstall") {
-        await service.uninstall({ env: process.env, stdout: process.stdout });
+        await withWizardProgress(
+          "Gateway daemon",
+          { doneMessage: "Gateway daemon uninstalled." },
+          async (progress) => {
+          progress.update("Uninstalling Gateway daemon…");
+          await service.uninstall({ env: process.env, stdout: process.stdout });
+          },
+        );
       }
     }
 
@@ -138,37 +165,46 @@ export async function finalizeOnboardingWizard(options: FinalizeOnboardingOption
     ) {
       const devMode =
         process.argv[1]?.includes(`${path.sep}src${path.sep}`) && process.argv[1]?.endsWith(".ts");
-      const nodePath = await resolvePreferredNodePath({
-        env: process.env,
-        runtime: daemonRuntime,
-      });
-      const { programArguments, workingDirectory } = await resolveGatewayProgramArguments({
-        port: settings.port,
-        dev: devMode,
-        runtime: daemonRuntime,
-        nodePath,
-      });
-      if (daemonRuntime === "node") {
-        const systemNode = await resolveSystemNodeInfo({ env: process.env });
-        const warning = renderSystemNodeWarning(systemNode, programArguments[0]);
-        if (warning) await prompter.note(warning, "Gateway runtime");
-      }
-      const environment = buildServiceEnvironment({
-        env: process.env,
-        port: settings.port,
-        token: settings.gatewayToken,
-        launchdLabel:
-          process.platform === "darwin"
-            ? resolveGatewayLaunchAgentLabel(process.env.CLAWDBOT_PROFILE)
-            : undefined,
-      });
-      await service.install({
-        env: process.env,
-        stdout: process.stdout,
-        programArguments,
-        workingDirectory,
-        environment,
-      });
+      await withWizardProgress(
+        "Gateway daemon",
+        { doneMessage: "Gateway daemon installed." },
+        async (progress) => {
+        progress.update("Preparing Gateway daemon…");
+        const nodePath = await resolvePreferredNodePath({
+          env: process.env,
+          runtime: daemonRuntime,
+        });
+        const { programArguments, workingDirectory } = await resolveGatewayProgramArguments({
+          port: settings.port,
+          dev: devMode,
+          runtime: daemonRuntime,
+          nodePath,
+        });
+        if (daemonRuntime === "node") {
+          const systemNode = await resolveSystemNodeInfo({ env: process.env });
+          const warning = renderSystemNodeWarning(systemNode, programArguments[0]);
+          if (warning) await prompter.note(warning, "Gateway runtime");
+        }
+        const environment = buildServiceEnvironment({
+          env: process.env,
+          port: settings.port,
+          token: settings.gatewayToken,
+          launchdLabel:
+            process.platform === "darwin"
+              ? resolveGatewayLaunchAgentLabel(process.env.CLAWDBOT_PROFILE)
+              : undefined,
+        });
+
+        progress.update("Installing Gateway daemon…");
+        await service.install({
+          env: process.env,
+          stdout: process.stdout,
+          programArguments,
+          workingDirectory,
+          environment,
+        });
+        },
+      );
     }
   }
 
@@ -353,16 +389,23 @@ export async function finalizeOnboardingWizard(options: FinalizeOnboardingOption
   await prompter.note(
     hasWebSearchKey
       ? [
-          "Web search is ready.",
+          "Web search is enabled, so your agent can look things up online when needed.",
+          "",
           webSearchKey
-            ? "Brave API key: stored in config (tools.web.search.apiKey)."
-            : "Brave API key: provided via BRAVE_API_KEY env var.",
+            ? "API key: stored in config (tools.web.search.apiKey)."
+            : "API key: provided via BRAVE_API_KEY env var (Gateway environment).",
           "Docs: https://docs.clawd.bot/tools/web",
         ].join("\n")
       : [
-          "Recommended: set up a Brave Search API key for web_search.",
-          "Easiest: clawdbot configure --section web (stores tools.web.search.apiKey).",
-          "Env alternative: BRAVE_API_KEY (gateway environment).",
+          "If you want your agent to be able to search the web, you’ll need an API key.",
+          "",
+          "Clawdbot uses Brave Search for the `web_search` tool. Without a Brave Search API key, web search won’t work.",
+          "",
+          "Set it up interactively:",
+          "- Run: clawdbot configure --section web",
+          "- Enable web_search and paste your Brave Search API key",
+          "",
+          "Alternative: set BRAVE_API_KEY in the Gateway environment (no config changes).",
           "Docs: https://docs.clawd.bot/tools/web",
         ].join("\n"),
     "Web search (optional)",