How do I install the Trail Checkin skill?

Run npx skillmds@latest add glebis/trail-checkin in your terminal (requires Node.js), paste this page's agent-chat prompt into Claude, Cursor, or any MCP-connected agent, or download the SKILL.md file and copy it into your agent's skills directory.

Is Trail Checkin safe to use?

This skill has not completed SkillMD's automated safety review yet. Capability flags: executes scripts. SkillMD never runs a skill's scripts for you; review the SKILL.md before installing.

Which AI agents work with Trail Checkin?

This skill is tagged as working with Claude Code, Claude.ai, OpenAI Codex. SKILL.md is an open format, so most agents that read a skills directory can load it too.

Is Trail Checkin free to use?

Yes. Installing skills from SkillMD is free, and the skill stays under its author's original license.

Who published Trail Checkin?

glebis (@glebis) published this skill. Their other Agent Skills are listed on their SkillMD profile.

Trail Checkin by glebis — Agent Skill

Name: Trail Checkin
Rating: 4.5 (4 reviews)
Author: glebis

Trail Checkin

Interactive trail review and update process for Obsidian vault at ~/Brains/brain. Lists available Trails, lets you select which to check in with, then walks through structured questions for each (progress, markers, tasks, metrics, open questions, status, next review date) and updates the trail file. Use for weekly reviews, milestone moments, context switching, or monthly reflection. Triggers on /trail-checkin.

glebis f69edc2 3 files · 14.4 KB Updated Sep 9, 2026

File contents

Base directory for this skill: ~/.Codex/skills/trail-checkin

Trail Check-in Skill

Interactive trail review and update process. Lists available trails, lets you select which to check in with, then walks through structured questions for each trail to capture progress, update markers, and reflect on direction.

Prerequisites

Obsidian vault at ~/Brains/brain
Trails located in ~/Brains/brain/Trails/
Trail files follow naming pattern Trail - *.md

Usage

Run the skill to start an interactive check-in:

/trail-checkin

Or invoke directly:

python3 ~/.Codex/skills/trail-checkin/scripts/trail_checkin.py

How It Works

Step 1: List Trails

Script scans Trails/ folder and extracts:

Trail name
Status (active/paused/completed)
Last updated date
Objective (first line summary)

Returns JSON with trail list.

Step 2: Select Trails

Codex uses AskUserQuestion with multiSelect to let you choose which trails to check in with.

Step 3: Check-in Questions (per trail)

For each selected trail, Codex asks:

Progress made - What happened since last check-in?
Markers to add - Any new milestones reached?
Tasks completed - Which tasks can be marked done?
New tasks - What needs to be added?
Metrics update - Any numbers to update?
Open questions - New questions or resolved ones?
Status change - Still active? Paused? Completed?
Next review date - When to check in again?

Step 4: Update Trails

Codex updates each trail file with:

New progress markers
Updated metrics
Task status changes
New open questions
Updated last_updated date
Next review date

Output

Returns summary of updates made to each trail.

Example Session

User: /trail-checkin

Codex: Found 5 trails. Which would you like to check in with?
[multiSelect: Mental Health Tech, Codex Lab, Telegram Agent, Salience, Voice Codex]

User: [selects Mental Health Tech, Voice Codex]

Codex: Let's check in with Trail: Mental Health Tech

What progress have you made since last update (2026-01-19)?
[short answer input]

User: Published Vastaamo hack post, drafted privacy ethics analysis

Codex: Should we add any progress markers?
[yes/no]

[continues through questions...]

Codex: Updated Trail: Mental Health Tech
- Added marker: Vastaamo hack post published
- Updated posts metric: 78
- Marked task complete: Publish privacy post
- Updated last_updated: 2026-01-19

Now checking in with Trail: Voice Codex...

Script API

# List all trails
python3 scripts/trail_checkin.py list

# Get trail details
python3 scripts/trail_checkin.py show "Mental Health Tech"

Returns JSON for programmatic use.

When to Use

Weekly reviews
Project milestone moments
When switching contexts between trails
Monthly reflection sessions
When a trail needs status update

---name: trail-checkindescription: Interactive trail review and update process for Obsidian vault at ~/Brains/brain. Lists available Trails, lets you select which to check in with, then walks through structured questions for each (progress, markers, tasks, metrics, open questions, status, next review date) and updates the trail file. Use for weekly reviews, milestone moments, context switching, or monthly reflection. Triggers on /trail-checkin.--- Base directory for this skill: ~/.Codex/skills/trail-checkin # Trail Check-in Skill Interactive trail review and update process. Lists available trails, lets you select which to check in with, then walks through structured questions for each trail to capture progress, update markers, and reflect on direction. ## Prerequisites - Obsidian vault at `~/Brains/brain` - Trails located in `~/Brains/brain/Trails/` - Trail files follow naming pattern `Trail - *.md` ## Usage Run the skill to start an interactive check-in: ```bash /trail-checkin ``` Or invoke directly: ```bash python3 ~/.Codex/skills/trail-checkin/scripts/trail_checkin.py ``` ## How It Works ### Step 1: List Trails Script scans `Trails/` folder and extracts: - Trail name - Status (active/paused/completed) - Last updated date - Objective (first line summary) Returns JSON with trail list. ### Step 2: Select Trails Codex uses `AskUserQuestion` with multiSelect to let you choose which trails to check in with. ### Step 3: Check-in Questions (per trail) For each selected trail, Codex asks: 1. **Progress made** - What happened since last check-in? 2. **Markers to add** - Any new milestones reached? 3. **Tasks completed** - Which tasks can be marked done? 4. **New tasks** - What needs to be added? 5. **Metrics update** - Any numbers to update? 6. **Open questions** - New questions or resolved ones? 7. **Status change** - Still active? Paused? Completed? 8. **Next review date** - When to check in again? ### Step 4: Update Trails Codex updates each trail file with: - New progress markers - Updated metrics - Task status changes - New open questions - Updated `last_updated` date - Next review date ## Output Returns summary of updates made to each trail. ## Example Session ``` User: /trail-checkin Codex: Found 5 trails. Which would you like to check in with? [multiSelect: Mental Health Tech, Codex Lab, Telegram Agent, Salience, Voice Codex] User: [selects Mental Health Tech, Voice Codex] Codex: Let's check in with Trail: Mental Health Tech What progress have you made since last update (2026-01-19)? [short answer input] User: Published Vastaamo hack post, drafted privacy ethics analysis Codex: Should we add any progress markers? [yes/no] [continues through questions...] Codex: Updated Trail: Mental Health Tech - Added marker: Vastaamo hack post published - Updated posts metric: 78 - Marked task complete: Publish privacy post - Updated last_updated: 2026-01-19 Now checking in with Trail: Voice Codex... ``` ## Script API ```bash # List all trails python3 scripts/trail_checkin.py list # Get trail details python3 scripts/trail_checkin.py show "Mental Health Tech" ``` Returns JSON for programmatic use. ## When to Use - Weekly reviews - Project milestone moments - When switching contexts between trails - Monthly reflection sessions - When a trail needs status update

Frequently asked questions