gloss-auto-tag

name	gloss-auto-tag
description	Auto-tag highlights in the current conversation using AI analysis. Use when asked to 'auto-tag', 'tag my highlights', 'gloss:auto-tag', or '/gloss:auto-tag'.
one_liner	AI-powered auto-tagging of conversation highlights.
activation_triggers	["gloss:auto-tag","auto-tag","auto tag","tag my highlights","tag highlights","When user wants Claude to automatically categorize/tag their highlights"]

/gloss:auto-tag — Auto-Tag Highlights

Read highlights from the current session, analyze them, and apply semantic tags automatically.

Script

bun <GLOSS_DIR>/src/cli.ts

Where <GLOSS_DIR> is the directory containing this skill (the repo root).

Procedure

1. Find the current session ID:

   • Use the working directory to build the encoded project path (replace / with -)
   • Find the most recently modified JSONL:

     ls -t ~/.claude/projects/-<ENCODED_CWD>/*.jsonl | head -1
     

   • Extract the session ID from the filename

2. Fetch all highlights for this session:

   bun <GLOSS_DIR>/src/cli.ts highlights --json --session "<session-id>"
   

3. If no highlights exist, tell the user they need to make highlights first via /gloss:convo.

4. Analyze each highlight and assign tags. Consider:

   • The highlighted text — what topic does it cover?
   • The comment — did the user add context?
   • The kind — decision, bug, constraint, todo, question, insight, highlight
   • The speaker — user vs assistant gives context on what's being captured
   • Existing tags — preserve any tags the user already set manually

   Use these tag categories as a guide (but don't force-fit — use whatever tags genuinely match):

   Category	Example tags
   Topic	architecture, testing, security, performance, refactoring, api-design
   Technology	typescript, rust, sqlite, websocket, css, react
   Action	action-item, follow-up, blocked, resolved, deferred
   Quality	pattern, anti-pattern, best-practice, gotcha, workaround
   Scope	breaking-change, config, migration, dependency, docs

5. Build the tag payload — a JSON array of {id, tags} objects:

   [
     {"id": "a1b2c3d4", "tags": ["architecture", "pattern", "typescript"]},
     {"id": "e5f6g7h8", "tags": ["bug", "sqlite", "resolved"]}
   ]
   

   Rules:

   • Merge with existing tags — don't drop tags the user already set
   • Keep tags lowercase, hyphenated (e.g., api-design not API Design)
   • 2-5 tags per highlight is ideal; don't over-tag
   • If a highlight already has good tags, skip it

6. Apply tags via batch-tag:

   echo '<json-array>' | bun <GLOSS_DIR>/src/cli.ts batch-tag
   

7. Report results:

   • Show each highlight with its new tags
   • Summarize: "Tagged N highlights with M unique tags"
   • List the unique tags used for easy reference

Example Output

Tagged 8 highlights with 14 unique tags:

  a1b2c3d4: "The server-first pivot makes live the default..."
    → [architecture, server, pivot] (was: [])

  e5f6g7h8: "replaceAnnotationTags() transaction in Step 7"
    → [sqlite, bug, codex-finding] (was: [bug])

Unique tags: architecture, server, pivot, sqlite, bug, codex-finding, ...