diff --git a/packages/cli/src/commands/init.ts b/packages/cli/src/commands/init.ts
index 9206817..5dcf188 100644
--- a/packages/cli/src/commands/init.ts
+++ b/packages/cli/src/commands/init.ts
@@ -219,6 +219,23 @@ const initWorkspaceCommand = defineCommand({
   },
 });
 
+async function tryRequireSqlite(nerveRoot: string): Promise<boolean> {
+  try {
+    const modulePath = join(nerveRoot, "node_modules", "better-sqlite3");
+    // Use a child process to test if the native module loads
+    const { execFile } = await import("node:child_process");
+    const { promisify } = await import("node:util");
+    const execFileAsync = promisify(execFile);
+    await execFileAsync("node", ["-e", `require(${JSON.stringify(modulePath)})`], {
+      cwd: nerveRoot,
+      timeout: 10_000,
+    });
+    return true;
+  } catch {
+    return false;
+  }
+}
+
 async function runInitWorkspace(force: boolean): Promise<void> {
   const nerveRoot = getNerveRoot();
 
@@ -242,20 +259,36 @@ async function runInitWorkspace(force: boolean): Promise<void> {
   );
 
   process.stdout.write("Installing dependencies…\n");
+  const { cmd, installArgs } = await detectPackageManager();
   try {
-    const { cmd, installArgs } = await detectPackageManager();
     await runCommand(cmd, installArgs, nerveRoot);
+  } catch {
+    process.stdout.write(
+      `⚠️ Install failed. Try manually:\n   cd ${nerveRoot} && ${cmd} ${installArgs.join(" ")}\n`,
+    );
+  }
 
-    process.stdout.write("Rebuilding native module better-sqlite3…\n");
-    try {
-      await runCommand(cmd, ["rebuild", "better-sqlite3"], nerveRoot);
-    } catch {
+  // Verify better-sqlite3 native module — rebuild up to 2 times if broken
+  const sqlitePath = join(nerveRoot, "node_modules", "better-sqlite3");
+  if (existsSync(sqlitePath)) {
+    for (let attempt = 1; attempt <= 2; attempt++) {
+      if (await tryRequireSqlite(nerveRoot)) break;
       process.stdout.write(
-        "⚠️ rebuild better-sqlite3 failed — if the daemon fails to start, reinstall from the workspace directory.\n",
+        `${attempt === 1 ? "Building" : "Retrying build of"} native module better-sqlite3 (attempt ${attempt}/2)…\n`,
+      );
+      try {
+        await runCommand(cmd, ["rebuild", "better-sqlite3"], nerveRoot);
+      } catch {
+        // will be caught by the verify below
+      }
+    }
+    if (!(await tryRequireSqlite(nerveRoot))) {
+      process.stdout.write(
+        `⚠️ better-sqlite3 native module is not working. The daemon will fail to start.\n` +
+          `   Fix: cd ${nerveRoot} && ${cmd} rebuild better-sqlite3\n` +
+          `   Or:  npm install --build-from-source better-sqlite3\n`,
       );
     }
-  } catch {
-    process.stdout.write("⚠️ Install failed — you may need to install dependencies manually.\n");
   }
 
   if (!existsSync(join(nerveRoot, ".git"))) {