diff --git a/packages/examples/cli-demo/src/cli.ts b/packages/examples/cli-demo/src/cli.ts
index 63c08ae39f..3a8fecc7a8 100644
--- a/packages/examples/cli-demo/src/cli.ts
+++ b/packages/examples/cli-demo/src/cli.ts
@@ -361,7 +361,8 @@ export function formatTurnFailure(reason: TurnEndReason): string {
 
 /**
  * Execute one CLI invocation. Argument and boot failures never write stdout;
- * every booted context is disposed before this promise resolves.
+ * context disposal is awaited before return, and its failure does not replace
+ * an earlier diagnostic.
  * @param args - arguments after the executable name.
  * @param runtime - optional injected process boundaries for tests and embedding.
  * @returns the ordinary process exit code; the thin bin overrides it for Unix signals.
@@ -421,7 +422,7 @@ export async function executeCli(args: readonly string[], runtime: CliRuntime =
       try {
         await disposeContext(ctx)
       } catch (error: unknown) {
-        diagnostic ??= `${CLI_NAME}: dispose failed: ${toError(error).message}\n`
+        diagnostic = `${diagnostic ?? ''}${CLI_NAME}: dispose failed: ${toError(error).message}\n`
         exitCode = 1
       }
     }
diff --git a/packages/examples/cli-demo/tests/cli.spec.ts b/packages/examples/cli-demo/tests/cli.spec.ts
index fcdf8a3004..8c41236829 100644
--- a/packages/examples/cli-demo/tests/cli.spec.ts
+++ b/packages/examples/cli-demo/tests/cli.spec.ts
@@ -398,6 +398,18 @@ describe('runOneShot and executeCli', () => {
     expect(disposalOutput.stderr).toContain('dispose exploded')
   })
 
+  it('reports disposal failure alongside an earlier run failure', async () => {
+    const ctx = new Context()
+    liveContexts.push(ctx)
+    const output = await invoke(ctx, ['task'], { failDispose: true })
+    expect(output).toEqual({
+      code: 1,
+      stdout: '',
+      stderr: 'dsh-cli-demo: config must create exactly one top-level agent, found 0\n'
+        + 'dsh-cli-demo: dispose failed: dispose exploded\n',
+    })
+  })
+
   it('cancels startup work and queued work before the correlated turn begins', async () => {
     const startup = await harness(['hang'])
     let started!: () => void