Task and Session Assistant

A Claude Cowork skill that monitors your autonomous sessions and notifies you when something needs attention.

What it does

Task and Session Assistant runs as a scheduled task (default: every 2 hours) and silently monitors all your active Cowork/Dispatch sessions. It only notifies you when it finds something worth your attention — hung tasks, error loops, stalled progress, or tasks waiting for your input overnight.

It never stops or interrupts your work. It observes, classifies issues by severity, prepares recovery context, and sends you a consolidated notification with clear recommendations.

Features

• Pattern-based hang detection — Catches unanswered AskUserQuestion, stalled progress, and error loops
• Scaled turn-count thresholds — Different limits for research tasks, config/fix tasks, and long-running jobs
• Quiet hours mode (10pm–8am) — More aggressive severity escalation overnight
• Concurrent session monitoring — Flags when you exceed your session cap
• Recovery context preparation — Pre-builds recovery summaries with copy-paste respawn prompts
• Daily health dashboard — HTML report with KPIs, hang rate trends, and cleanup recommendations
• Anomaly tracking — Learns which tool combinations tend to cause problems
• Long-running task heartbeats — Relaxed thresholds and progress updates for overnight jobs

Installation

Install the .skill file in Claude Cowork, then set up a scheduled task to run it every 2 hours:

Cron: 0 */2 * * *

Configuration

All settings are in references/configuration.md. Key options:

Setting	Default
Quiet hours	10pm – 8am
Concurrent session cap	3
Recovery context	Enabled
Dashboard generation	Daily at 8am
Session cleanup threshold	7 days idle

See the configuration file for the full list and example profiles (relaxed / tight monitoring).

Structure

task-and-session-assistant/
├── SKILL.md                          # Main scheduled task prompt
├── CHANGELOG.md                      # Version history
├── references/
│   ├── configuration.md              # User-customizable settings
│   └── detection-patterns.md         # Hang detection logic details
├── scripts/
│   └── generate_dashboard.py         # Daily digest HTML generator
└── assets/
    └── dashboard_template.html       # Dashboard HTML template

Version

Current: 2.0.0 (notify-only model)

See CHANGELOG.md for version history.