Problem

During live Slack + Playwright sessions, agents often generate screenshots in one session folder and then fail to attach them in the next turn/session because attach_file historically required current-session paths.

Observed failure pattern in daemon logs:

• Tool [attach_file] ... Error: File path must be within the session directory (...)
• Agent then manually copies files into the current session directory and retries.

This is partially mitigated by PR #148 (cross-session import support in attach_file), but the agent behavior is still brittle because skill guidance is not explicit or discoverable enough.

Why this matters

• Extra tool calls and retries waste tokens and latency.
• Agents appear unreliable even when tools are technically available.
• Skills are becoming too ad hoc; we need a narrower, predictable route for common workflows.

Proposed scope

1. Add a first-class skill for screenshot handoff (playwright-screenshot-handoff) that teaches agents to:
   • save screenshots into the current session workspace when possible, and
   • use attach_file directly (or import path) without manual copy loops.
2. Add explicit trigger metadata for this skill so it activates for terms like:
   • playwright, screenshot, attach, send image, upload file.
3. Add a concise skill-system cleanup pass (tapering):
   • reduce overlapping skill prompts,
   • improve deterministic routing for high-frequency operational workflows.

Acceptance criteria

• Agents can complete navigate -> screenshot -> attach in one pass without path-related retries.
• Session logs show no repeated attach_file path errors for this workflow.
• Skill triggers are explicit and testable.
• Add tests or scripted evals that assert successful screenshot handoff behavior.

Related

• PR Reduce attach_file friction for screenshot handoff between sessions #148 (attach_file cross-session import hardening)
• Follow-up area: broader skill-system simplification and routing consistency