aws / aws/amazon-q-developer-cli

Kiro CLI 2.8.0 - Authentication failed on every prompt after login

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Dominant language
Rust
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Forks
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Description

### Checks

- [x] I have searched [github.com/aws/amazon-q-developer-cli/issues](https://github.com/aws/amazon-q-developer-cli/issues?q=) and there are no duplicates of my issue
- [x] I have run `q doctor` in the affected terminal session
- [x] I have run `q restart` and replicated the issue again

### Operating system

Linux 7.0.0-22-generic - Ubuntu 26.04 LTS

### Expected behaviour

After a successful login, Kiro CLI should answer prompts normally and return model responses.

### Actual behaviour

Every prompt returns:

Authentication failed. Your session may have expired. Run `kiro-cli login` to re-authenticate.

This happens even after:
- logout/login
- removing ~/.kiro
- updating to Kiro CLI 2.8.0
- successful whoami
- successful doctor

### Steps to reproduce

1. Run kiro-cli login
2. Verify with kiro-cli whoami
3. Run kiro-cli chat --legacy-ui
4. Ask any question (e.g. "Who discovered Brazil?")
5. CLI shows "Authentication failed. Your session may have expired."

### Environment

```yaml
OS: Ubuntu 26.04 LTS
Kiro CLI: 2.8.0
Plan: KIRO FREE
Authentication: Builder ID

Commands tested:
- kiro-cli login
- kiro-cli logout
- kiro-cli whoami
- kiro-cli doctor
- kiro-cli chat --legacy-ui

Additional details:
- Login succeeds
- whoami succeeds
- doctor reports "Everything looks good"
- MCP server loads successfully
- Model is shown as "claude-sonnet-4"
- Any prompt results in:
"Authentication failed. Your session may have expired."
```

Contributor guide

Open the contributing guide

Research direction

Start by reproducing the failure with kiro-cli login, whoami, doctor, and chat --legacy-ui on Ubuntu 26.04 with Kiro CLI 2.8.0 and Builder ID authentication. Trace the authentication flow from these CLI entry points; done means a successful login allows prompts to return model responses instead of the authentication error.

Written by the indexing model from the issue text.

Assessment

Tech stack
cli, rust
Domain
authentication, cli
Issue type
Bug
Difficulty
4/5
Estimated time
3-5 days
Activity status
Quiet
Clarity
Mostly clear
Newbie friendliness
35/100

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