diff --git a/.changeset/cutover-aware-ao-update.md b/.changeset/cutover-aware-ao-update.md
new file mode 100644
index 000000000..7934a3f0d
--- /dev/null
+++ b/.changeset/cutover-aware-ao-update.md
@@ -0,0 +1,11 @@
+---
+"@aoagents/ao-cli": minor
+---
+
+Teach `ao update` to perform the legacy-to-rewrite cutover (bridge 0.9.6).
+
+When a rewrite build is published under the npm `next` dist-tag (or `AO_CUTOVER_VERSION` is set) and the current install is still legacy (`major.minor < 0.10`), `ao update` now migrates the user's data via `ao migrate` (issue #2129) and installs the rewrite at the exact pinned version instead of running the normal channel update.
+
+The cutover flow: refuse if any active worker session is running (the orchestrator's own state never blocks), require a terminal confirmation (never auto-confirm a dashboard/api-invoked spawn), stop the daemon without restoring, run migration before the install replaces the legacy binary, install the rewrite, verify the new version, and finish without restarting the legacy daemon. `--check` now also reports `cutoverAvailable` and `cutoverTarget`.
+
+When no `next` build exists (the common case), `ao update` behaves exactly as before across all install methods.
diff --git a/packages/cli/src/commands/update.ts b/packages/cli/src/commands/update.ts
index ea70135aa..19c97eb6d 100644
--- a/packages/cli/src/commands/update.ts
+++ b/packages/cli/src/commands/update.ts
@@ -404,7 +404,9 @@ interface MigrationResult {
  * from stdout — the contract is documented on {@link MigrationSummary}.
  */
 async function runMigration(): Promise<MigrationResult> {
-  const result = await runCommandCapture("ao", ["migrate", "--json"], { echo: true });
+  // No echo: `--json` emits a machine-readable blob, not human progress. We
+  // surface a readable summary on success and the raw output on failure.
+  const result = await runCommandCapture("ao", ["migrate", "--json"]);
   return {
     exitCode: result.exitCode,
     summary: parseMigrationSummary(result.output),
@@ -412,6 +414,13 @@ async function runMigration(): Promise<MigrationResult> {
   };
 }
 
+/** One-line human summary of a migration result, for the success path. */
+function formatMigrationSummary(summary: MigrationSummary | null): string {
+  if (!summary) return "Migration complete.";
+  const { projects, orchestrators } = summary;
+  return `Migration complete: ${projects.created} project(s), ${orchestrators.created} orchestrator(s) migrated.`;
+}
+
 function parseMigrationSummary(output: string): MigrationSummary | null {
   const match = output.match(/\{[\s\S]*\}/);
   if (!match) return null;
@@ -513,13 +522,15 @@ async function handleCutover(method: InstallMethod, target: string): Promise<voi
     console.error(
       chalk.red(`\nMigration failed (exit ${migration.exitCode}). AO was NOT updated.`),
     );
+    if (migration.output.trim()) console.error(chalk.dim(migration.output.trim()));
     console.error(
       chalk.yellow(
-        "You are still on the legacy version. Resolve the migration error above and retry `ao update`.",
+        "You are still on the legacy version. Resolve the migration error and retry `ao update`.",
       ),
     );
     process.exit(migration.exitCode);
   }
+  console.log(chalk.dim(formatMigrationSummary(migration.summary)));
 
   // 5. Install the rewrite at the target.
   const cmd = getCutoverInstallCommand(method, target);