[CI Failure] Flaky: AppHostServerSessionTests.Start_StopRequested_GracefulIgnored_ExpireEscalatesToTreeKill times out intermittently on Windows

## Build Information

Build: https://github.com/microsoft/aspire/actions/runs/32812190860
Build error leg or test failing: Tests / Cli / Cli (windows-latest) / `Aspire.Cli.Tests.Projects.AppHostServerSessionTests.Start_StopRequested_GracefulIgnored_ExpireEscalatesToTreeKill`
Pull request: #19032

## Error Message

```
System.TimeoutException : The operation has timed out.
at Aspire.Cli.Tests.Projects.AppHostServerSessionTests.Start_StopRequested_GracefulIgnored_ExpireEscalatesToTreeKill() in D:\a\aspire\aspire\tests\Aspire.Cli.Tests\Projects\AppHostServerSessionTests.cs:line 294
```

## Description

Flaky: AppHostServerSessionTests.Start_StopRequested_GracefulIgnored_ExpireEscalatesToTreeKill times out intermittently on Windows

**Type**: flaky-test

## Occurrences

| Date | Build | Job | PR |
|------|-------|-----|----|
| 2026-08-25 | [32812190860](https://github.com/microsoft/aspire/actions/runs/32812190860) | Tests / Cli / Cli (windows-latest) | #19032 |

Start with tests/Aspire.Cli.Tests/Projects/AppHostServerSessionTests.cs at line 294 and run AppHostServerSessionTests.Start_StopRequested_GracefulIgnored_ExpireEscalatesToTreeKill on windows-latest. Investigate the intermittent TimeoutException in the Windows CI job and verify the test completes reliably without timing out.

Written by the indexing model from the issue text.